Cyclohexane derivative

Abstract: A novel liquid crystal material having an alkenyl group at the end of the molecule, and having a low viscosity, and when the compound is added, being able to reduce the threshold voltage of the resulting display element, is provided, the compound being expressed by the formula (I), wherein X is a F atom, a trifluoromethyl group, a trifluoromethoxy group or a difluoromethoxy group, -A- is 1,4-cyclohexylene or 1,4-phenylene, -B- is 1,4-cyclohexylene, l is 0, 1 or 2, m is 0, 1 or 2, l+m≧1, Z is -CH₂CH₂- or single bond, n is an integer of 0 to 4, R is a H atom or a linear or branched alkyl group of 1-7C, and when R is an alkyl group, the double bond has a trans-configuration. The compounds of the present invention are suitable as liquid crystal material for STN display element, and further is chemically stable; hence it is possible to prepare a composition having a superior multiplex characteristic and capable of effecting a low voltage drive.

Description: BACKGROUND OF THE INVENTION 1. Field of the Invention This invention relates to a cyclohexane derivative useful as a liquid crystal material. More particularly, it relates to a liquid crystalline compound having an alkenyl group at the end of its molecule and a liquid crystal composition containing the compound. 2. Description of the Related Art Display elements utilizing liquid crystals have been broadly used for watches, electronic calculators, etc. These liquid crystal display elements are those utilizing the optical anisotropy and the dielectric anisotropy of liquid crystal substances. Liquid crystal phases include nematic liquid crystal phase, smectic liquid crystal phase and cholesteric liquid crystal phase, and among the above phases liquid crystal display elements utilizing nematic liquid crystal phase have been most broadly and practically used. Such display elements include those of TN (twisted nematic) mode, DS (dynamic scattering) mode, guest-host mode, DAP mode, etc., corresponding to the electro-optic effect applied to liquid crystal display, and as the liquid crystal substances utilized for the respective display elements, those exhibiting liquid crystal phases within a temperature range as broad as possible in the natural in the nature are preferred. A large number of liquid crystal compounds have already been known, but at present, there is no single liquid crystal substance satisfying such conditions, but several kinds of liquid crystal substances or non-liquid crystal compounds have been mixed to be practically used. These substances are required to be stable to moisture, light, heat, air, etc. In particular, recently, there has been increasing an importance of substances having a low optical anisotropy, as a material for liquid crystal display element for active matrix mode represented by thin film transistor (TFT) mode. Further, it has been required for the liquid crystal material that its compatibility with a number of already existing liquid crystal materials is as large as possible at low temperatures. DE-A-40 25 550 discloses phenyl cyclohexanes of the following formula which are suitable for STN mode displays wherein n is 0-7, Q 1 and Q 2 are H or one of Q 1 and Q 2 is CH 3 , r is 0-5, A is trans-1,4-cyclohexylene, 1,4-phenylene, 3-fluoro-1,4-phenylene or a single bond, X is F, Cl, -CF 3 , -CN, -OCF 3 or OCHF 2 , and Y and Z independently represent H or F, provided that Y and/or Z are F if simultaneously A is a single bond, Q 1 and Q 2 represent H and X is CN. The following compounds have so far been known as compounds similar to those of the present invention: These compounds, particularly (I), (II), (III), (VI) and (VII), have been reported to have a large dielectric anisotropy value (Δε) and a low viscosity and exhibit an effect of lowering the threshold voltage without raising the viscosity. However, according to research of the present inventors, it has been found that the Δε value is comparatively small and the threshold voltage cannot be sufficiently lowered. SUMMARY OF THE INVENTION The object of the present invention is to provide a cyclohexane derivative as a liquid crystal compound which has a low viscosity and can sufficiently lower the threshold voltage. The present inventors have made extensive research in order to solve the above mentioned problems, and as a result, have found a compound having a novel structure and having improved characteristics ever known liquid crystal compounds, and have completed the present invention. The compounds of the present invention are expressed by the formula (I) wherein X represents a fluorine atom, a trifluoromethyl group, trifluoromethoxy group or difluoromethoxy group, -A- represents 1,4-cyclohexylene or 1,4-phenylene, -B-represents 1,4-cyclohexylene, l represents 0, 1 or 2, m represents 0, 1 or 2, and l+m≧1, Z represents -CH 2 CH 2 - or a single bond, n represents an integer of 0 to 4, R represents a hydrogen atom or a linear or branched alkyl group of 1 to 7 carbon atoms, and when R represents an alkyl group, the double bond has a trans-configuration, and a liquid crystalline mixture containing at least one member of the cyclohexane derivative. DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS Compounds having an alkenyl substituent group, so far reported, have a higher elastic constant ratio (K 33 /K 11 ) than those of compounds having a normal alkyl substituent group, as reported in various papers, and hence they are suitable as a liquid crystal material for STN display elements. The characteristic of the liquid crystal compound provided by the present invention, surprisingly enough, has a lower elastic constant ratio (K 33 /K 11 ) than those of compounds having a normal alkyl substituent group, in spite of having an alkenyl substituent group. Materials having a low K 33 /K 11 are steep in the electro-optic characteristic of TN mode, and exhibit a superior multiplex characteristic. This fact is known for example by the following articles: a) J. Nehring, advance in Liquid Crystal Research and Applications (ed. L. Bata)., P1155. Pergamon Press (1980). b) G. Baur, The Physics and Chemistry of Liquid Crystal Devices (ed. G.J. Sprokel)., P61, Plenum (1980). c) Y. Takahashi, T. Uchida and M. Wada, Mol. Cryst. Liq. Cryst., 66, 171 (1981). Further, since the compound of the present invention is chemically stable, it is possible to prepare a composition having a superior multiplex characteristic and capable of effecting a low voltage drive by using the compound of the present invention. As the compound of the formula (I), compounds expressed by the formulas Ia to Ie can be exemplified (the definitions of the respective symbols are the same as those in the formula (I)). Particularly preferable compounds among those of the respective formulas will be illustrated below. Compounds of the formula (I) wherein R represents an alkyl group, form a trans-configuration in the aspect of the steric structure directed to the double bond having R bonded thereto. The alkyl group of R is preferably a linear alkyl group of 1 to 7 carbon atoms, more preferably a methyl group, ethyl group, propyl group, butyl group and pentyl group. The liquid crystal composition provided by the present invention is a liquid crystal dielectric comprising a component (A) containing at least one of the compounds expressed by the formula (I) and further, a component (B) containing at least one of compounds having a high dielectric anisotropy of preferably Δε≧5, a component (C) containing at least one of compounds having a low dielectric anisotropy of |Δε|<5 and a component (D) containing at least one of compounds having a clearing point exceeding 80°C, and further, if required, another component (E). Compounds particularly preferred as the component (B) will be shown below. In the above formulas, R" represents an alkyl group or an alkenyl group of 1 to 10 carbon atoms, and one carbon atom or two not-adjacent carbon atoms of the groups may be replaced by an oxygen atom. Compounds particularly preferred as the component (C) will be shown below. In these formulas, R" and R' each represent an alkyl group or an alkenyl group of 1 to 10 carbon atoms, and one carbon atom or two not-adjacent carbon atoms of the groups may be replaced by an oxygen atom. Particularly preferable compounds as the component (D) are shown below. In these compounds, R" and R' each represent an alkyl group or an alkenyl group of 1 to 10 carbon atoms, and one carbon atom or two not-adjacent carbon atoms of the groups may be replaced by an oxygen atom. Particularly preferable compounds as the component (E) are shown below. In these compounds, R" represents an alkyl group or an alkenyl group of 1 to 10 carbon atoms, and one carbon atom or two not-adjacent carbon atoms of the groups may be replaced by an oxygen atom. The composition according to the present invention is preferred to contain at least one of the compounds expressed by the formula (I) in a proportion of 0.1 to 40% by weight in the aspect of superiority of the resulting liquid crystal characteristics. Preparation of the compound The compound of the present invention can be obtained according to Wittig reaction (Organic Reaction Vol. 14, 270 (1965), that is, by reacting an aldehyde derivative expressed by the formula (II) wherein X represents a fluorin atom, trifluoromethyl group, trifluoromethoxy group or difluoromethoxy group, -A- represents 1,4-cyclohexylene or 1,4-phenylene, -B- represents 1,4-cyclohexylene, l represents 0, 1 or 2, m represents 0, 1 or 2, and 1+m≧1, Z represents -CH 2 CH 2 - or a single bond and n represents an integer of 0 to 4, with a phosphorus glide compound expressed by the formula (III) R 3 ' P=CH-R wherein R represents a hydrogen atom or a linear or branched alkyl group of 1 to 7 carbon atoms and R' represents an alkyl group, an aryl group or an aralkyl group. The compound of the present invention formed by the reaction of the compound of the formula (II) with that of the formula (III) is generally obtained in the form of a mixture of stereoisomers thereof, but the mixture can be separated for example according to a column chromatography. Further, if necessary, the mixture can be converted into the compound of the present invention according to a known method. Namely, by brominating the mixture with triphenylphosphinebromine and reducing the resulting halogenated compound, it is possible to convert to the mixture containing the compound of the present invention in a superior proportion. In the process for producing the compound of the present invention, the reaction of the compound expressed by the formula (II) with that expressed by the formula (III) can be carried out according to a known method. For example, it is possible to use a compound (III) obtained by reacting the corresponding phosphonium compound with, as a preferable base, potassium t-butoxide, sodium methoxide, lithium diisopropylamide n-butyl lithium sodium hydride, pyridine, triethylamine or the like. This reaction and the succeeding reaction with the compound (II) is generally carried out in an organic solvent. As the solvent usable in the present reaction, those which do not hinder the reaction may be sufficient. For example, diethyl ether, tetrahydrofuran, dioxane, benzene, toluene, hexane, methylene chloride, chloroform, dimethylsulfoxide, dimethylformamide, etc. are preferable, and they can be used as a single solvent or a mixed solvent. The reaction temperature can be chosen from among the range of -50°C to the boiling point of the solvent used. The reaction is preferably carried out at -30°C to room temperature, but when the raw material concentration in the reaction mixture is high, the reaction should be carried out at -30°C to 0°C. The compound expressed by the formula (II) as a starting substance for preparing the compound of the present invention can be prepared according to various methods represented by the following (1) to (5): In these formulas, R is as defined above, X represents a fluorine atom, trifluoromethyl group, trifluoromethoxy group or difluoromethoxy group, l represents 0, 1 or 2, m represents 0, 1 or 2, and l+m≧1, -Z- represents -CH 2 CH 2 - or a single bond, n represents an integer of 1 to 4, n' represents n-1, and m' representes 0 or 1. Examples The compound of the present invention will be described in more detail by way of Examples, but it should not be construed to be limited thereto. Example 1 Preparation of 5-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-2E-pentene (Compound No. 1) (1) Mg (17.1 g) was suspended in THF (100 ml) in a nitrogen gas stream, followed by dropwise adding a solution of 3,4,5-trifluorobromobenzene (162 g) dissolved in THF (400 ml) to the suspension, stirring the mixture at room temperature for one hour, dropwise adding a solution of 1,4-cyclohexanedionemonoethylene ketal (100 g) dissolved in tetrahydrofuran (THF) (400 ml), stirring the mixture at room temperature for one hour, adding a saturated aqueous solution of NH 4 Cℓ (1 l) after completion of the reaction, extracting with ethyl acetate (1 l), drying the organic layer over anhydrous MgSO 4 and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-hydroxy-4-(3',4',5'-trifluorophenyl)cyclohexane (166.2 g). (2) 1,1-Ethylenedioxy-4-hydroxy-4-(3',4',5'-trifluorophenyl)cyclohexane (166.2 g) was dissolved in toluene (500 ml), followed by adding p-toluenesulfonic acidmonohydrate (20 g) into the solution, stirring the mixture under reflux for one hour, washing the reaction solution with water (500 ml), drying the organic layer over anhydrous magnesium sulfate, and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-(3',4,'5'-trifluorophenyl)-3-cyclohexene (102.6 g). (3) 1,1-Ethylenedioxy-4-(3,4',5'-trifluorophenyl)-3-cyclohexene (100 g) was dissolved in ethanol (1 l), followed by adding Pd/C (5%) (40 g), stirring the mixture in a hydrogen gas atmosphere to carry out a catalytic reduction, filtering off the catalyst after the reaction, and distilling off the organic layer under reduced pressure, to obtain 1,1-ethylenedioxy4-(3',4',5'-trifluorophenyl)cyclohexane (95 g). (4) Formic acid (82.7 g) and toluene (20 ml) were added to 1,1-ethylenedioxy-4-(3',4',5'-trifluorophenyl)cyclohexane (95.02 g), followed by heating the mixture under reflux with stirring for 2 hours, adding the reaction solution to water (500 ml), extracting with ethyl acetate (1 l), drying the organic layer over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, and recrystallizing from ethanol, to obtain 4-(3',4',5'-trifluorophenyl)cyclohexanone (63.1 g). m.p. 123.5°C. (5) A suspension of 2-(1',3'-dioxan-2'-yl)ethyltriphenylphosphonium bromide (48.6 g) in THF (250 ml) was cooled down to 0°C with stirring in a nitrogen gas stream, followed by adding potassium-t-butoxide (14.9 g) little by little, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluorophenyl)cyclohexanone (20 g) in THF (100 ml), raising the temperature of the reaction mixture up to room temperature, further stirring it for 2 hours, adding to water (500 ml) after completion of the reaction, extracting with ethyl acetate (1 l), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure and subjecting to chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 3',4',5'-trifluorophenyl-4-(2'-(1 ,3 -dioxan-2 -yl)ethylidene)cyclohexane (24.9 g). (6) 3',4',5'-trifluorophenyl-4-(2'-(1'',3''-dioxan-2''-yl)ethylidene)cyclohexane (24.9 g) was dissolved in ethanol (200 ml), followed by adding Pd/C (5%) (15 g), stirring the mixture in a hydrogen gas atmosphere to carry out a catalytic reduction, filtering off the catalyst after completion of the reaction, distilling off the filtrate under reduced pressure and recrystallizing from ethanol according to a recrystallization procedure, to obtain 3',4',5'-trifluorophenyl-4-(2'-(1'',3''-dioxan-2''-yl)ethyl)cyclohexane (13.2 g). (7) Formic acid (10 g) and toluene (2 ml) were added to 3',4',5'-trifluorophenyl-4-(2'-(1'',3''-dioxan-2''-yl)ethyl)cyclohexane (13 g), followed by heating the mixture under reflux with stirring for 2 hours, adding the reaction solution to water (50 ml), extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous magnesium sulfate and concentrating under reduced pressure, to obtain 3-(4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)propionaldehyde (10.7 g). (8) A suspension of ethyltriphenylphosphonium bromide (11.2 g) in THF (50 ml) was stirred in a nitrogen gas atmosphere, followed by cooling it down to 0°C, adding potassium-t-butoxide (4.2 g) little by little, agitating the reaction solution at room temperature for one hour, dropwise adding a solution of 3-(4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)propionaldehyde (67.8 g) in THF (20 ml), raising the reaction mixture up to room temperature, further stirring it for 2 hours, adding to water (50 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous magnesium sulfate, concentrating under reduced pressure, and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 5-(4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)-2-pentene (4.09 g). (9) m-Chloroperbenzoic acid (7.7 g) and potassium carbonate (6.2 g) were fed into a solution of 5-(4'-(3'',4'',5''-trifluorophenyl)cyclohexyl-2-pentene (4.09 g) in methylene chloride (50 ml) to obtain a mixture, followed by stirring the mixture for 2 hours in an ice bath, adding water (50 ml), after completion of the reaction, extracting with methylene chloride (100 ml), drying the organic layer over anhydrous MgSO 4 and concentrating it under reduced pressure, to obtain 5-(4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)-2,3-epoxypentane (3.84 g). (10) Dibromotriphenylphosphine (12.3 g) was fed into a suspension of 5-(4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)-2,3-epoxypentane (3.84 g) in benzene (100 ml) to obtain a mixture, followed by heating the mixture under reflux with stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , concentrating it under reduced pressure, and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 5-(4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)-2,3-dibromopentane (3.33 g). (11) Zinc powder (3.2 g) was fed into a solution of 5-(4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)-2,3-dibromopentane (3.33 g) in acetic acid (50 ml) to obtain a mixture, followed by stirring the mixture at room temperature over night, filtering off solids after completion of the reaction, adding the filtrate to water (50 ml), extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), and recrystallizing from heptane, to obtain 5-(4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)-2E-pentene (320 mg). m.p. 13.8-16.9°C. Example 2 Preparation of 4-trans-(3',4',5'-trifluorophenyl)cyclohexyletene (Compound No. 2) (1) A suspension of methoxymethyltriphenylphosphonium chloride (36.4 g) in THF (200 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (12 g) little by little, while cooling the suspension at 0°C, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluorophenyl)cyclohexanone (20 g) in THF (100 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (200 ml), drying the organic layer over anhydrous MgSO 4 , concentrating it under reduced pressure, and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 4-(3',4',5'-trifluorophenyl)methoxymethylenecyclohexane (18.25 g). (2) THF (40 ml) and 2N hydrochloric acid (20 ml) were added to 4-(3',4',5'-trifluorophenyl)methoxymethylenecyclohexane (14.5 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (200 ml) after completion of the reaction, extracting with ethyl acetate (500 ml), drying the organic layer over anhydrous MgSO 4 , and concentrating under reduced pressure, to obtain 4-(3',4',5'-trifluorophenyl)cyclohexanecarbaldehyde (6.5 g). (3) A suspension of methyltriphenylphosphonium bromide (2.7 g) in THF (20 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (1.1 g) little by little, while cooling the suspension at 0°C, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluorophenyl)cyclohexanecarbaldehyde (1.5 g) in THF (5 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (50 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), and recrystallizing from heptane, to obtain 4-trans-(3',4',5'-trifluorophenyl)cyclohexylethene (1.05 g). m.p. 20.3-21.3°C. Example 3 Preparation of 4-trans-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexylethene (Compound No. 3) (1) Mg (3.4 g) was suspended in THF (20 ml) in a nitrogen gas stream, followed by dropwise adding a solution of 3,5-difluoro-4-trifluoromethylbromobenzene (40 g) in THF (100 ml) to the suspension, stirring the mixture at room temperature for one hour, dropwise adding a solution of 1,4-cyclohexanedionemonoethylene ketal (20 g) in THF (100 ml), stirring the mixture at room temperature for one hour, adding a saturated aqueous solution of NH 4 Cℓ (200 ml) after completion of the reaction, extracting with ethyl acetate (500 ml), drying the organic layer over anhydrous MgSO 4 , and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-hydroxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexane (23 g). (2) 1,1-Ethylenedioxy-4-hydroxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexane (23 g) was dissolved in toluene (200 ml), followed by adding p-toluenesulfonic acidmonohydrate (5 g) to the solution, stirring the mixture under reflux for one hour, allowing the mixture to cool down, washing the reaction solution with water (200 ml), drying the organic layer over anhydrous MgSO 4 , and distilling off the solvent, to obtain 1,1-ethylenedioxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)-3-cyclohexene (17.3 g). (3) 1,1-Ethylenedioxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)-3-cyclohexene (17.3 g) was dissolved in ethanol (200 ml), followed by adding Pd/C (5%) (5 g), carrying out a catalytic reduction with stirring in a hydrogen gas atmosphere, filtering off the catalyst after completion of the reaction, and distilling off the organic layer under reduced pressure, to obtain 1,1-ethylenedioxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexane (15.7 g). (4) Formic acid (11.3 g) and toluene (5 ml) were added to 1,1-ethylenedioxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexane (15.7 g), followed by heating the mixture under reflux with stirring for 2 hours, adding the reaction solution to water (50 ml), extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , and distilling off the solvent under reduced pressure, to obtain 4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexanone (12.0 g). (5) A suspension of methoxymethyltriphenylphosphonium chloride (7 g) in THF (20 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (2.9 g) little by little, while cooling the suspension at 0°C, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexanone (4.7 g) in THF (30 ml), raising the temperature of the reaction mixture up to room temperature, further stirring it for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (200 ml), drying the organic layer over anhydrous MgSO 4 , concentrating it under reduced pressure, and carrying out chromatography treatment on silica gel, with ethyl acetate/heptane (1:5), to obtain 4-(3',5'-difluoro-4'-trifluoromethylphenyl)methoxymethylenecyclohexane (2.06 g). (6) THF (10 ml) and 2N hydrochloric acid (10 ml) were added to 4-(3',5'-difluoro-4'-trifluoromethylphenyl)methoxymethylenecyclohexane (2.06 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (20 ml) after completion of the reaction, extracting with ethyl acetate (50 ml), drying the organic layer over anhydrous MgSO 4 , and concentrating under reduced pressure, to obtain 4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexanecarbaldehyde (1.99 g). (7) A suspension of methyltriphenylphosphonium bromide (3 g) in THF (10 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (1.2 g) little by little, while cooling the suspension at 0°C, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexanecarbaldehyde (1.99 g) in THF (5 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (20 ml) after completion of the reaction, extracting with ethyl acetate (50 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5) and recrystallizing from heptane, to obtain 4-trans-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexylethene (300 mg). The following compounds are prepared according to the above-mentioned procedure: Compound Nos.: 4. 3-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-2E-propene 5. 3-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-1-propene 6. 4-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-1-butene m.p. 16.8-19.3°C 7. 4-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-2E-butene 8. 4-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-3E-butene 9. 5-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-1-pentene 10. 5-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-3E-pentene 11. 5-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-4E-pentene 12. 6-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-1-hexene 13. 5-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-2E-hexene 14. 6-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-3E-hexene 15. 5-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-4E-hexene 16. 7-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-2E-heptene 17. 7-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-3E-heptene 18. 7-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-4E-heptene 19. 8-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-3E-octene 20. 8-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-4E-octene 21. 9-(4'-trans-(3'',4'',5''-trifluorophenyl)cyclohexyl)-4E-nonene 22. 3-(4'-trans-(3'',4'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -2E-propene 23. 3-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -1-propene 24. 4-(4'-trans(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -1-butene 25. 4-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -2E-butene 26. 4-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -3E-butene 27. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -1-pentene 28. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -2E-pentene 29. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -3E-pentene 30. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -4E-pentene 31. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -1-hexene 32. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -2E-hexene 33. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -3E-hexene 34. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -4E-hexene 35. 7-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -2E-heptene 36. 7-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -3E-heptene 37. 7-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -4E-heptene 38. 8-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -3E-octene 39. 8-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -4E-octene 40. 9-(4'-trans-(3'',5''-difluoro-4''-trifluoromethylphenyl)cyclohexyl) -4E-nonene 41. 2-(4'-trans-(3''-,5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) ethene 42. 3-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -2E-propene 43. 3-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -1-propene 44. 4-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -1-butene 45. 4-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -2E-butene 46. 4-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -3E-butene 47. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -1-pentene 48. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -2E-pentene 49. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -3E-pentene 50. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -4E-pentene 51. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -1-hexene 52. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -2E-hexene 53. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -3E-hexene 54. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -4E-hexene 55. 7-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -2E-heptene 56. 7-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -3E-heptene 57. 7-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -4E-heptene 58. 8-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -3E-octene 59. 8-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -4E-octene 60. 9-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxylphenyl)cyclohexyl) -4E-nonene 61. 2-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) ethene 62. 3-(4'-trans-(3'',5''-difluoro-4'-difluoromethoxylphenyl)cyclohexyl) -2E-propene 63. 3-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -1-propene 64. 4-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -1-butene 65. 4-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -2E-butene 66. 4-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -3E-butene 67. 5-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -1-pentene 68. 5-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -2E-pentene 69. 5-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -3E-pentene 70. 5-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -4E-pentene 71. 6-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -1-hexene 72. 6-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -2E-hexene 73. 6-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -3E-hexene 74. 6-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -4E-hexene 75. 7-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -2E-heptene 76. 7-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -3E-heptene 77. 7-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -4E-heptene 78. 8-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -3E-octene 79. 8-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -4E-octene 80. 9-(4'-trans(3'',5''-difluoro-4''-difluoromethoxylphenyl)cyclohexyl) -4E-nonene Example 4 Preparation of 2-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)ethene (Compound No. 81) (1) Flaked Mg (11.6 g, 0.477 mol) was placed in a 2 l capacity, three-neck flask, followed by adding THF (100 ml) in a nitrogen gas stream, dropwise adding a solution of 3,4,5-trifluorobromobenzene (91.6 g, 0.434 mol) in THF (200 ml) with stirring at a velocity of keeping 30°C, stirring the mixture at room temperature for 2 hours after completion of the dropwise addition, dropwise adding to the reaction solution, a solution of 4,4'-dicyclohexanedionemonoethylene acetal (94 g, 0.395 mol) in THF (200 ml) over 45 minutes so as to keep its temperature at 30°C or lower, stirring the mixture at room temperature for 2 hours after completion of the dropwise addition, allowing the reaction solution to stand overnight, again stirring the reaction solution, adding a saturated aqueous solution of NH 4 Cℓ little by little, extracting the resulting solution three times with ethyl acetate (400 ml), washing the organic layer with water, drying it over anhydrous MgSO 4 , and concentrating under reduced pressure, to obtain 4-hydroxy-4-(3',4',5'-trifluorophenyl)dicyclohexaneethylene acetal (125 g, GC 79%) in the form of yellow-brown solids. This product was used for the subsequent reaction without purification. (2) The above reaction product (125 g) was dissolved in toluene (500 ml), in a 2 l capacity three-neck flask equipped with Dean-Stark's device, followed by adding Amberlist-15 (6.5 g), heating the mixture under reflux with stirring for 4 hours, cooling the solution down to room temperature after completion of the reaction, filtering off the Amberlist-15, concentrating the mother liquor under reduced pressure and separating and purifying the residue according to silica gel chromatography, to obtain 4-(3',4',5'-trifluorophenyl)-3'- dicyclohexen-4-one ethylene acetal (85 g). m.p. 107.0-114.0°C. (3) 4-(3',4',5'-Trifluorophenyl)-3'-dicyclohexen-4-one ethylene acetal (66 g) was placed in a 1 l capacity three-neck flask and dissolved in a mixed solvent of ethyl acetate/ethanol (3:1) (500 ml), followed by adding Pd/C (5 wt%) catalyst (5 g) to the solution, stirring the mixture in a hydrogen gas atmosphere, completing the stirring when absorption of the hydrogen gas was not observed, filtering off the catalyst and concentrating the resulting solution under reduced pressure, to obtain a transparent oily substance. This substance was recrystallized from ethanol and purified, to obtain trans-4-(3',4',5'-trifluorophenyl)dicyclohexane-4-one ethylene acetal (24 g). m.p. 101.0-104.5°C. (4) Trans-4-(3',4',5'-trifluorophenyl)-dicyclohexan-4-one ethylene acetal (24 g) was placed in a 200 ml capacity, egg-plant type flask, followed by dissolving it in toluene (100 ml), adding formic acid (15.6 g) to the solution, heating the mixture under reflux with stirring for 4 hours, cooling it down to room temperature after completion of the reaction, adding ethyl acetate (200 ml), washing with water, drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure to obtain white crystals, and recrystallizing them from n-heptane for purification, to obtain 4-(trans-4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)cyclohexanone (17 g). m.p. 96.7-99.6°C. (5) Methoxymethyltriphenylphosphonium chloride (16.5 g) was placed in a 300 ml capacity three-neck flask, and added THF (100 ml) to obtain a suspension, followed by adding potassium-t-butoxide (6.5 g) to the suspension while keeping the temperature at -10°C or lower, stirring the mixture at -10°C for one hour, dropwise adding a solution of 4-(trans-4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)cyclohexanone (10 g) in THF (80 ml) at a speed of keeping -10°C, stirring the mixture at the temperature for one hour, further stirring at room temperature for 2 hours, adding water (100 ml) after completion of the reaction, extracting three times with ethyl acetate (100 ml), washing the organic layer with water, drying over anhydrous MgSO 4 , concentrating under reduced pressure to obtain white solids, and isolating and purifying them according to silica gel column chromatography, to obtain 4-(trans-4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)methoxymethylenecyclohexane (10.2 g) (white crystals). m.p. 78.4-81.2°C. (6) 4-(Trans-4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)methoxymethylenecyclohexane (10.2 g) was placed in a 300 ml capacity egg-plant type flask, followed by adding THF (80 ml) to obtain a solution, adding 2N-hydrochloric acid (30 ml) to the solution, heating the mixture with stirring for 2 hours, cooling down to room temperature after completion of the reaction, adding water (30 ml), extracting three times with ethyl acetate (50 ml), washing the organic layer with water, drying over anhydrous MgSO 4 , and concentrating under reduced pressure, to obtain 4-(trans-4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)cyclohexanecarbaldehyde (6 g) (a transparent oily substance). This product was used for the subsequent reaction without purification. (7) Methyltriphenylphosphonium bromide (14.0 g) was placed in a 300 ml capacity three-neck flask, followed by adding THF (100 ml) to obtain a suspension, adding potassium-t-butoxide (5.3 g) to the suspension while keeping a temperature of -10°C or lower, stirring the mixture at -10°C for one hour, dropwise adding a solution of 4-(trans-4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)cyclohexanecarbaldehyde (8.5 g) in THF (100 ml) at a speed of keeping -10°C, stirring the mixture at the temperature for one hour, further stirring at room temperature for 2 hours, adding water (100 ml) after completion of the reaction, extracting three times with ethyl acetate (100 ml), washing the organic layer with water, drying over anhydrous MgSO 4 and concentrating under reduced pressure to obtain white solids. The aimed product was isolated from the solids according to silica gel column chromatography, recrystallized and purified to obtain trans-(4-(trans-4'-(3'',4'',5''-trifluorophenyl)cyclohexyl)cyclohexylethene (3.8 g) (white crystals). This product exhibited liquid crystal phases: C-N point, 57.1-58.8°C and N-I point, 69.2-71.3°C. The following compounds are prepared according to the above procedure: 82. 3-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-2E-propene 83. 3-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-1-propene 84. 4-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-1-butene C-N point, 64.1°C and N-I point, 99.1°C 85. 4-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-2E-butene 86. 4-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-3E-butene 87. 5-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-1-pentene 88. 5-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-2E-pentene 89. 5-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-3E-pentene 90. 5-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-4E-pentene 91. 6-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-1-hexene 92. 6-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-2E-hexene 93. 6-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-3E-hexene 94. 6-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-4E-hexene 95. 7-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-2E-heptene 96. 7-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-3E-heptene 97. 7-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-4E-heptene 98. 8-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-3E-octene 99. 8-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-4E-octene 100. 9-(4'-trans-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)cyclohexyl)-4E-nonene 101. 2-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)ethene 102. 3-(4'-trans-(4''-trans-(3''',5''',-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-2E-propene 103. 3-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-1-propene 104. 4-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-1-butene 105. 4-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-2E-butene 106. 4-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-3E-butene 107. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-1-pentene 108. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-2E-pentene 109. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-3E-pentene 110. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-4E-pentene 111. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-1-hexene 112. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-2E-hexene 113. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-3E-hexene 114. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-4E-hexene 115. 7-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-2E-heptene 116. 7-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-3E-heptene 117. 7-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-4E-heptene 118. 8-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-3E-octene 119. 8-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-4E-octene 120. 9-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethylpheny)cyclohexyl)cyclohexyl)-4E-nonene 121. 2-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)ethene 122. 3-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-2E-propene 123. 3-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1-propene 124. 4-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1-butene 125. 4-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-2E-butene 126. 4-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-3E-butene 127. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1-pentene 128. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-2E-pentene 129. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-3E-pentene 130. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-4E-pentene 131. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1-hexene 132. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-2E-hexene 133. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-3E-hexene 134. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-4E-hexene 135. 7-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-2E-heptene 136. 7-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-3E-heptene 137. 7-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-4E-heptene 138. 8-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-3E-octene 139. 8-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-4E-octene 140. 9-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-4E-nonene 141. 2-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)ethene 142. 3-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-2E-propene 143. 3-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1-propene 144. 4-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1-butene 145. 4-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-2E-butene 146. 4-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-3E-butene 147. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1-pentene 148. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-2E-pentene 149. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-3E-pentene 150. 5-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-4E-pentene 151. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1-hexene 152. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-2E-hexene 153. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-3E-hexene 154. 6-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-4E-hexene 155. 7-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-2E-heptene 156. 7-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-3E-heptene 157. 7-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-4E-heptene 158. 8-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-3E-octene 159. 8-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-4E-octene 160. 9-(4'-trans-(4''-trans-(3''',5'''-difluoro-4'''-difluoromethoxyphenyl)cyclohexyl)cyclohexyl)-4E-nonene Example 5 Preparation of 2-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl)ethene (Compound No. 161) (1) A suspension of 3,4,5-trifluorobenzyltriphenylphosphonium bromide (234 g) in THF (500 ml) was stirred in a nitrogen gas stream, followed by adding sodium methoxide (32.4 g) little by little at room temperature, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-formylcyclohexanone (50 g) in THF (250 ml), stirring the mixture at room temperature for 2 hours, adding it to water (1 l), extracting with ethyl acetate (1 l), washing the organic layer with water, drying over anhydrous MgSO 4 , concentrating the solvent under reduced pressure, to obtain 4-(2'-(3'',4'',5''-trifluorophenyl)ethenyl)cyclohexanone (71 g). (2) 4-(2'-(3'',4'',5''-Trifluorophenyl)ethenyl)cyclohexanone (71 g) was dissolved in ethanol (500 ml), followed by adding Pd/C (5%) (2.0 g), hydrogenating the compound in a hydrogen gas atmosphere with stirring till the hydrogen absorption was completed, filtering off the catalyst after completion of the reaction, and concentrating the solvent under reduced pressure, to obtain 4-(2'-(3'',4'',5''-trifluorophenyl)ethyl)cyclohexanone (70 g). (3) A suspension of methoxymethyltriphenylphosphonium chloride (112.3 g) in THF (300 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (45.4 g) little by little while cooling at 0°C, stirring the reaction solution at room temperature for one hour, dropwise adding 4-(2'-(3'',4'',5''-trifluorophenyl)ethyl)cyclohexanone (70 g) in THF (200 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (500 ml) after completion of the reaction, extracting with ethyl acetate (500 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure, and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 4-(2'-(3'',4'',5''-trifluorophenyl)ethyl)methoxymethylenecyclohexane (53.7 g). (4) THF (100 ml) and 2N-hydrochloric acid (100 ml) were added to 4-(2'-(3'',4'',5''-trifluorophenyl)ethyl)methoxymethylenecyclohexane (20 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (300 ml) after completion of the reaction, extracting with ethyl acetate (300 ml), drying the organic layer over anhydrous MgSO 4 and concentrating under reduced pressure, to obtain 4-(2'-(3'',4'',5''-trifluorophenyl)ethyl)cyclohexanecarbaldehyde (17 g). (5) A suspension of methyltriphenylphosphonium bromide (27 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide little by little under cooling at 0°C, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(2'-(3'',4'',5''-trifluorophenyl)ethyl)cyclohexanecarbaldehyde (17 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature, further stirring it for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5) and crystallizing from heptane, to obtain 2-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl)ethene (9 g). The following compounds are prepared according to the above procedure: Compound Nos. 162. 3-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -1-propene 163. 3-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -2E-propene 164. 4-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -1-butene 165. 4-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -2E-butene 166. 4-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -3E-butene 167. 5-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -1-pentene 168. 5-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -2E-pentene 169. 5-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -3E-pentene 170. 5-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -4E-pentene 171. 6-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -1-hexene 172. 6-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -2E-hexene 173. 6-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -3E-hexene 174. 6-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -4E-hexene 175. 7-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -2E-heptene 176. 7-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -3E-heptene 177. 7-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -4E-heptene 178. 8-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -3E-octene 179. 8-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -4E-octene 180. 9-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl) -4E-nonene 181. 2-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)ethene 182. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-2E-propene 183. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-1-propene 184. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-1-butene 185. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-2E-butene 186. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-3E-butene 187. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-1-pentene 188. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-2E-pentene 189. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-3E-pentene 190. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-4E-pentene 191. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-1-hexene 192. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-2E-hexene 193. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-3E-hexene 194. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-4E-hexene 195. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-2E-heptene 196. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-3E-heptene 197. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-4E-heptene 198. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-3E-octene 199. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-4E-octene 200. 8-(4'-trans-(2''-(3''',5''',-difluoro-4'''-trifluoromethylphenyl)ethyl)cyclohexyl)-4E-nonene 201. 2-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)ethene 202. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-2E-propene 203. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-1-propene 204. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-1-butene 205. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-2E-butene 206. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-3E-butene 207. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-1-pentene 208. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-2E-pentene 209. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-3E-pentene 210. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-4E-pentene 211. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-1-hexene 212. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-2E-hexene 213. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-3E-hexene 214. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-4E-hexene 215. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-2E-heptene 216. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-3E-heptene 217. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-4E-heptene 218. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-3E-octene 219. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-4E-octene 220. 9-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxylphenyl)ethyl)cyclohexyl)-4E-nonene 221. 2-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)ethene 222. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-2E-propene 223. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-1-propene 224. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-1-butene 225. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-2E-butene 226. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-3E-butene 227. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-1-pentene 228. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-2E-pentene 229. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-3E-pentene 230. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-4E-pentene 231. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-1-hexene 232. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-2E-hexene 233. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-3E-hexene 234. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-4E-hexene 235. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-2E-heptene 236. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-3E-heptene 237. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-4E-heptene 238. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-3E-octene 239. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-4E-octene 240. 9-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxylphenyl)ethyl)cyclohexyl)-4E-nonene Example 6 Preparation of 2-(4'-trans -(2''-(4'''-trans-(3'''',4'''',5'''' -trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)ethene (Compound No. 241) (1) A suspension of triethyl phosphonoacetate (21.8 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (11.8 g) little by little at room temperature, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluorophenyl)cyclohexanone (20 g) in THF (50 ml), stirring at room temperature for 2 hours, adding to water (100 ml), extracting with ethyl acetate (100 ml), washing the organic layer with water, drying over anhydrous MgSO 4 , and concentrating the solvent under reduced pressure, to obtain 4-(3',4',5'-trifluorophenyl)ethoxycarbonylmethylenecyclohexane (18.3 g). (2) 4-(3',4',5'-Trifluorophenyl)ethoxycarbonylmethylenecyclohexane (18.3 g) was dissolved in ethanol (100 ml), followed by adding Pd/C (5%, 5 g), stirring the mixture, hydrogenating in a hydrogen gas atmosphere until completion of absorption of a hydrogen, filtering off the catalyst after completion of the reaction, and concentrating the solvent under reduced pressure, to obtain 4-(3',4',5' -trifluorophenyl)ethoxycarbonylmethylcyclohexane (17.2 g). (3) Lithiumaluminium hydride (2.2 g) was added to a solution of 4-(3',4',5'-trifluorophenyl)ethoxycarbonylmethylcyclohexane (17.2 g) in THF (100 ml), followed by stirring the mixture at room temperature for 2 hours, adding ethyl acetate (100 ml) little by little after completion of the reaction, further adding 2N hydrochloric acid (50 ml), washing the organic layer with water, drying over anhydrous MgSO 4 and concentrating the solvent under reduced pressure, to obtain 4-(3',4',5'-trifluorophenyl)-1-(2'-hydroxyethyl)cyclohexane (10.4 g). (4) 4-(3',4',5'-Trifluorophenyl)-1-(2'-hydroxyethyl)cyclohexane (10.4 g) was added to an aqueous solution of 47% HBr (15 ml), followed by stirring the mixture under reflux for 2 hours, adding the reaction solution to water (50 ml), extracting with ethyl acetate (100 ml), washing the organic layer with water, drying over anhydrous MgSO 4 , and concentrating the solvent under reduced pressure, to obtain 4-(3',4',5'-trifluorophenyl)-1-(2'-bromoethyl)cyclohexane (10.4 g). (5) Mg (0.7 g) was suspended in THF (10 ml) in a nitrogen gas stream, followed by dropwise adding a solution of 4-(3',4',5'-trifluorophenyl)-1-(2'-bromoethyl)cyclohexane (9.8 g) in THF (50 ml), into the suspension, stirring the mixture at room temperature for one hour, dropwise adding a solution of 1,4-cyclohexanedionemonoethylene ketal (4 g) in THF (30 ml), stirring the mixture at room temperature for one hour, adding a saturated aqueous solution of NH 4 Cℓ (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-hydroxy-4-(2'-(4''-(3''',4''',5'''-trifluorophenyl)cyclohexyl)ethylcyclohexane (8.2 g). (6) p-Toluenesulfonic acidmonohydrate (1 g) was added to a solution of 1,1-ethylenedioxy-4-hydroxy-4-(2'-(4''-(3''',4''', 5'''-trifluorophenyl)cyclohexyl)ethylcyclohexane (8.2 g) in toluene (100 ml), followed by stirring the mixture under reflux for one hour, washing the reaction solution with water (100 ml), drying the organic layer over anhydrous MgSO 4 , and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-(2'-(4''-(3''',4''',5''' -trifluorophenyl)cyclohexyl)ethyl)-3-cyclohexene (6.7 g). (7) Pd/C (5%) (1 g) was added to a solution of 1,1-ethylenedioxy-(2'-(4''-(3''',4''',5'''-trifluorophenyl)cyclohexyl)ethyl)-3-cyclohexene (6.7 g) in ethanol (200 ml), followed by carrying out catalytic reduction in a hydrogen gas atmosphere, filtering off the catalyst after completion of the reaction and distilling off the solvent from the organic layer under reduced pressure, to obtain 1,1-ethylenedioxy-(2'-(4''-(3''',4''',5'''-trifluorophenyl)cyclohexyl) ethyl)cyclohexane (6.2 g). (8) Formic acid (5 g) and toluene (2 ml) were added to 1,1-ethylenedioxy-(2'-(4''-(3'''-,4''',5'''-trifluorophenyl)cyclohexyl)ethyl)cyclohexane (6.2 g), followed by heating the mixture under reflux with stirring for 2 hours, pouring the reaction solution into water (20 ml), extracting with ethyl acetate (50 ml), drying the organic layer over anhydrous MgSO 4 , distilling off the solvent under reduced pressure, and recrystallizing from ethanol, to obtain 4-(2'-(4''-trans(3''',4''',5'''-trifluorophenyl)cyclohexyl)ethyl)cyclohexanone (4.9 g). (9) A suspension of methoxymethyltriphenylphosphonium chloride (6.2 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (2 g) little by little while cooling at 0°C, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(2'-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)ehtyl)cyclohexanone (4.9 g) in THF (20 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure, and carrying out chromatography treatment in silica gel with ethyl acetate/heptane (1:5), to obtain 4-(2'-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)ethyl)methoxymethylenecyclohexane (3.8 g). (10) THF (10 ml) and 2N hydrochloric acid (10 ml) were added to 4-(2'-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)ethyl)methoxymethylenecyclohexane (3.8 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (50 ml) after completion of the reaction, extracting with ethyl acetate (50 ml), drying the organic layer over anhydrous MgSO 4 and concentrating under reduced pressure, to obtain 4-(2'-(4''-trans-(3''',4''',5''' -trifluorophenyl)cyclohexyl)ethyl)cyclohexanecarbaldehyde (3.5 g). (11) A suspension of methyltriphenylphosphonium bromide (3.5 g) in THF (20 ml) was stirred in a nitrogen gas stream, followed by cooling it down to 0°C, adding potassium-t-butoxide (13 g) little by little, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(2'-(4''-trans-(3''',4''',5'''-trifluorophenyl)cyclohexyl)ethyl)cyclohexanecarbaldehyde (3.5 g) in THF (20 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (50 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5) and recrystallizing from heptane, to obtain 2-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5'''' -trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)ethene (2.2 g). The following compounds are prepared according to the above procedure: Compound Nos. 242. 3-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1-propene 243. 3-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-2E-propene 244. 4-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene 245. 4-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-2E-butene 246. 4-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-3E-butene 247. 5-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1-pentene 248. 5-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-2E-pentene 249. 5-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-3E-pentene 250. 5-(4'trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-4E-pentene 251. 6-(4'-trans-(2''-(4''''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)1-hexene 252. 6-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-2E-hexene 253. 6-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-3E-hexene 254. 6-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-4E-hexene 255. 7-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-2E-heptene 256. 7-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-3E-heptene 257. 7-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-4E-heptene 258. 8-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-3E-octene 259. 8-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-4E-octene 260. 9-(4'-trans-(2''-(4'''-trans-(3'''',4'''',5''''-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-4E-nonene 261. 2-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene 262. 3-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-propene 263. 3-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-propene 264. 4-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene 265. 4-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-butene 266. 4-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-butene 267. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-pentene 268. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-pentene 269. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-pentene 270. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-pentene 271. 6-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-hexene 272. 6-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-hexene 273. 6-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-hexene 274. 6-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-hexene 275. 7-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-heptene 276. 7-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-heptene 277. 7-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-heptene 278. 8-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-octene 279. 8-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-octene 280. 9-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-nonene 281. 2-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)ethene 282. 3-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-propene 283. 3-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1-propene 284. 4-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene 285. 4-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-butene 286. 4-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-butene 287. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1-pentene 288. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-pentene 289. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-pentene 290. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-pentene 291. 6-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1-hexene 292. 6-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-hexene 293. 6-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-hexene 294. 6-(4'-trans-(2''-(4''''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-hexene 295. 7-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-heptene 296. 7-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-heptene 297. 7-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-heptene 298. 8-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-octene 299. 8-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-octene 300. 9-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-nonene 301. 2-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)ethene 302. 3-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-propene 303. 3-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1-propene 304. 4-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene 305. 4-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-butene 306. 4-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-butene 307. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1-pentene 308. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-pentene 309. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-pentene 310. 5-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-pentene 311. 6-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1-hexene 312. 6-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-hexene 313. 6-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-hexene 314. 6-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-hexene 315. 7-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-2E-heptene 316. 7-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-heptene 317. 7-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-heptene 318. 8-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-3E-octene 319. 8-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-octene 320. 9-(4'-trans-(2''-(4'''-trans-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-4E-nonene Example 7 Preparation of 2-(4'-trans-(4''-trans-(2'''-(3'''', 4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)ethene (Compound No. 321) (1) A suspension of 3,4,5-trifluorobenzyltriphenylphosphonium bromide (51.5 g) in THF (100 ml) was stirred in a nitrogen gas stream, followed by adding sodium methoxide (6.2 g) little by little at room temperature, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(4'-formylcyclohexyl)cyclohexanone (20 g) in THF (50 ml), stirring the mixture at room temperature for 2 hours, adding to water (500 ml), extracting with ethyl acetate (500 ml), washing the organic layer with water, drying over anhydrous MgSO 4 , and concentrating the solvent under reduced pressure, to obtain 4-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethenyl)cyclohexyl)cyclohexanone (22.5 g). (2) 4-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethenyl)cyclohexyl)cyclohexanone (22.5 g) was dissolved in ethanol (250 ml), followed by adding Pd/C (5%) (5 g), stirring the mixture, hydrogenating in a hydrogen gas atmosphere till completion of absorption of a hydrogen gas, filtering off the catalyst after completion of the reaction, and concentrating the solvent under reduced pressure, to obtain 4-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl)cyclohexanone (20.4 g). (3) A suspension of methoxymethyltriphenylphosphonium chloride (23 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by cooling it down to 0°C, adding potassium-t-butoxide (8.2 g) little by little, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl)cyclohexanone (20.4 g) in THF (100 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, pouring into water (250 ml) after completion of the reaction, extracting with ethyl acetate (250 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure, and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 4-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl)methoxymethylenecyclohexane (15.6 g). (4) THF (30 ml) and 2N hydrochloric acid (30 ml) were added to 4-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl)methoxymethylenecyclohexane (15.6 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , and concentrating under reduced pressure, to obtain 4-(4'-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl)cyclohexanecarbaldehyde (13.7 g). (5) A suspension of methyltriphenylphosphonium bromide (15.2 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (5.3 g) little by little while cooling at 0°C, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(4'-trans-(2''-(3''',4''',5'''-trifluorophenyl)ethyl)cyclohexyl)cyclohexanecarbaldehyde (13.7 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure, carrying out chromatography on silica gel with ethyl acetate/heptane (1:5) and recrystallizing from heptane, to obtain 2-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5'''' -trifluorophenyl)ethyl)cyclohexyl)ethene (8.2 g). The following compounds are prepared according to the above procedure: 322. 3-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-1-propene 323. 3-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-2E-propene 324. 4-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-1-butene 325. 4-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-2E-butene 326. 4-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-3E-butene 327. 5-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-1-pentene 328. 5-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-2E-pentene 329. 5-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-3E-pentene 330. 5-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-4E-pentene 331. 6-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-1-hexene 332. 6-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-2E-hexene 333. 6-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-3E-hexene 334. 6-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-4E-hexene 335. 7-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-2E-heptene 336. 7-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-3E-heptene 337. 7-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-4E-heptene 338. 8-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-3E-octene 339. 8-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-4E-octene 340. 9-(4'-trans-(4''-trans-(2'''-(3'''',4'''',5''''-trifluorophenyl)ethyl)cyclohexyl)cyclohexyl)-4E-nonene 341. 2-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)ethene 342. 3-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-propene 343. 3-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-1-propene 344. 4-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-1-butene 345. 4-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-butene 346. 4-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-butene 347. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-trifluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-1-pentene 348. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-pentene 349. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-pentene 350. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-pentene 351. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-1-hexene 352. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-hexene 353. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-hexene 354. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-hexene 355. 7-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-heptene 356. 7-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-heptene 357. 7-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-heptene 358. 8-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-octene 359. 8-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-octene 360. 9-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-nonene 361. 2-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)ethene 362. 3-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-propene 363. 3-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-1-propene 364. 4-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-1-butene 365. 4-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-butene 366. 4-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-butene 367. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-1-pentene 368. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-pentene 369. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-pentene 370. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-pentene 371. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-1-hexene 372. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-hexene 373. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-hexene 374. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-hexene 375. 7-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-heptene 376. 7-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-heptene 377. 7-(4'-trans-(4''-trans(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-heptene 378. 8-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-octene 379. 8-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-octene 380. 9-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-nonene 381. 2-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)ethene 382. 3-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-propene 383. 3-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-1-propene 384. 4-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-1-butene 385. 4-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-butene 386. 4-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-butene 387. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-1-pentene 388. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-pentene 389. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-pentene 390. 5-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-pentene 391. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-1-hexene 392. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-hexene 393. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-hexene 394. 6-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-hexene 395. 7-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-2E-heptene 396. 7-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-heptene 397. 7-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-heptene 398. 8-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-3E-octene 399. 8-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluormethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-octene 400. 9-(4'-trans-(4''-trans-(2'''-(3'''',5''''-difluoro-4''''-difluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)-4E-nonene Example 8 Preparation of 2-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenyl)cyclohexyl)ethene (Compound No. 401) (1) 4-(3'',4'',5''-Trifluorophenyl)-3'-dicyclohexen-4-one ethylene acetal (20 g) and DDQ (2,3-dichloro-5,6-dicyanobenzoquinone) (16.7 g) were dissolved in toluene (200 ml), followed by stirring the solution under reflux for 4 hours, filtering off deposited insolubles, washing the organic layer with water, drying over anhydrous MgSO 4 , distilling off the solvent under reduced pressure, and purifying the resulting raw product according to column chromatography using silica gel (eluting solvent: ethyl acetate/heptane (1:5), to obtain 4-(3',4',5'-trifluoro-4''-biphenyl)cyclohexan-4-one ethylene acetal (13.9 g). (2) Formic acid (10 g) and toluene (2 ml) were added to 4-(3',4',5'-trifluoro-4''-biphenyl)cyclohexan-4-one ethylene acetal (13.9 g), followed by heating the mixture under reflux with stirring for 2 hours, adding the reaction solution to water (50 ml), extracting with ethyl acetate (50 ml), drying the organic layer over anhydrous MgSO 4 and distilling off the solvent under reduced pressure, to obtain 4-(3',4',5'-trifluoro-4''-biphenyl)cyclohexanone (11.5 g). (3) A suspension of methoxymethyltriphenylphosphonium chloride (13.6 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (48 g) little by little while cooling at 0°C, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluoro-4''-biphenyl)cyclohexanone (11.5 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 4-(3',4',5'-trifluoro-4''-biphenyl)methoxymethylenecyclohexane (8.8 g). (4) THF (50 ml) and 2N hydrochloric acid (50 ml) were added to 4-(3',4',5'-trifluoro-4''-biphenyl)methoxymethylenecyclohexane (8.8 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 and concentrating under reduced pressure, to obtain 4-(3',4',5'-trifluoro-4''-biphenyl)cyclohexanecarbaldehyde (7.5 g). (5) A suspension of methyltriphenylphosphonium bromide (9 g) in THF (20 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (3.1 g) little by little while cooling at 0°C, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluoro-4''-biphenyl)cyclohexanecarbaldehyde (7.5 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), and recrystallizing from heptane, to obtain 2-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenyl)cyclohexyl)ethene (4.6 g). The following compounds are prepared according to the above procedure: Compound No. 402. 3-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-1-propene 403. 3-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-2E-propene 404. 4-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-1-butene 405. 4-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-2E-butene 406. 4-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-3E-butene 407. 5-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-1-pentene 408. 5-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-2E-pentene 409. 5-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-3E-pentene 410. 5-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenyl)cyclophexyl)-4E-pentene 411. 6-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenyl)cyclohexyl)-1-hexene 412. 6-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenyl)cyclohexyl)-2E-hexene 413. 6-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-3E-hexene 414. 6-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenyl)cyclohexyl)-4E-hexene 415. 7-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenyl)cyclohexyl)-2E-heptene 416. 7-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-3E-heptene 417. 7-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-4E-heptene 418. 8-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-3E-octene 419. 8-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-4E-octene 420. 9-(4'-trans-(3'',4'',5''-trifluoro-4'''-biphenylyl)cyclohexyl)-4E-nonene 421. 2-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)ethene 422. 3-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenyl)cyclohexyl)-2E-propene 423. 3-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-1-propene 424. 4-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-1-butene 425. 4-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-2E-butene 426. 4-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-3E-butene 427. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-1-pentene 428. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-2E-pentene 429. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-3E-pentene 430. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-4E-pentene 431. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-1-hexene 432. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-2E-hexene 433. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-3E-hexene 434. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-4E-hexene 435. 7-(4'-trans-(3'',5''-difluoro-4''-trifluorometheyl-4'''-biphenylyl)cyclohexyl)-2E-heptene 436. 7-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-3E-heptene 437. 7-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-4E-heptene 438. 8-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-3E-octene 439. 8-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-4E-octene 440. 9-(4'-trans-(3'',5''-difluoro-4''-trifluoromethyl-4'''-biphenylyl)cyclohexyl)-4E-nonene 441. 2-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)ethene 442. 3-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-2E-propene 443. 3-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-1-propene 444. 4-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-1-butene 445. 4-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-2E-butene 446. 4-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-3E-butene 447. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-1-pentene 448. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-2E-pentene 449. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-3E-pentene 450. 5-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-4E-pentene 451. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-1-hexene 452. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-2E-hexene 453. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-3E-hexene 454. 6-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4''-biphenylyl)cyclohexyl)-4E-hexene 455. 7-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-2E-heptene 456. 7-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-3E-heptene 457. 7-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-4E-heptene 458. 8-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-3E-octene 459. 8-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-4E-octene 460. 9-(4'-trans-(3'',5''-difluoro-4''-trifluoromethoxy-4'''-biphenylyl)cyclohexyl)-4E-nonene 461. 2-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)ethene 462. 3-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-2E-propene 463. 3-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-1-propene 464. 4-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-1-butene 465. 4-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-2E-butene 466. 4-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-3E-butene 467. 5-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-1-pentene 468. 5-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-2E-pentene 469. 5-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-3E-pentene 470. 5-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-4E-pentene 471. 6-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-1-hexene 472. 6-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-2E-hexene 473. 6-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-3E-hexene 474. 6-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-4E-hexene 475. 7-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-2E-heptene 476. 7-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-3E-heptene 477. 7-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-4E-heptene 478. 8-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-3E-octene 479. 8-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-4E-octene 480. 9-(4'-trans-(3'',5''-difluoro-4''-difluoromethoxy-4'''-biphenylyl)cyclohexyl)-4E-nonene Example 9 Preparation of 2-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenyl)ehtyl)cyclohexyl)ethene (Compound No. 481). (1) Mg (2 g) was suspended in THF (10 ml) in a nitrogen gas stream, followed by dropwise adding a solution of 3,4,5-trifluorobromobenzene (19.0 g) in THF (150 ml), into the suspension, stirring the mixture at room temperature for one hour, dropwise adding a solution of 1,1-ethylenedioxy-4-(2'-(4''-oxocyclohexyl)ethyl)cyclohexane (20 g) in THF (50 ml), stirring the mixture at room temperature for one hour, adding a saturated aqueous solution of NH 4 Cℓ (200 ml) after completion of the reaction, extracting with ethyl acetate (500 ml), drying the organic layer over anhydrous MgSO 4 , and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-(2'-(4''-hydroxy-4''-(3''',4''',5'''-trifluorophenyl)cyclohexyl)ethylcyclohexane (23.8 g). (2) p-Toluenesulfonic acidmonohydrate (5 g) was added into a solution of 1,1-ethylenedioxy-4-(2'-(4''-hydroxy-4''-(3''', 4''',5'''-trifluorophenyl)cyclohexyl)ethyl)cyclohexane (23.8 g) in toluene (250 ml), followed by stirring the mixture under reflux for one hour, washing the reaction solution with water (250 ml), drying the organic layer over anhydrous MgSO 4 and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-(2'-(4''-(3''',4''',5'''-trifluorophenyl)-3''-cyclohexenyl)ethyl)cyclohexane (18.2 g). (3) 1,1-Ethylenedioxy-4-(2'-(4''-(3''',4''',5'''-trifluorophenyl)-3''-cyclohexenyl)ethyl)cyclohexane (18.2 g) and DDQ (14.1 g) were dissolved in toluene (250 ml), followed by stirring the mixture under reflux for 4 hours, filtering off deposited insolubles, washing the organic layer with water, drying over anhydrous MgSO 4 , distilling off the solvent under reduced pressure, and purifying the resulting raw product according to column chromatography on silica gel (eluent solvent: ethyl acetate/heptane = 1/5), to obtain 1,1-ethylenedioxy-4-(2'-(3'',4'',5''-trifluoro-4'''-biphenyl)ethyl)cyclohexane (12.6 g). (4) Formic acid (10 g) and toluene (2 ml) were added to 1,1-ethylenedioxy-4-(2'-(3'',4'',5''-trifluoro-4'''-biphenyl)ethyl)cyclohexane (12.6 g), followed by heating the mixture under reflux with stirring for 2 hours, adding the reaction solution to water (50 ml), extracting with ethyl acetate (50 ml), drying the organic solvent over anhydrous MgSO 4 , and distilling off the solvent under reduced pressure, to obtain 4-(2'-(3'',4'',5''-trifluoro-4'''-biphenyl)ethyl)cyclohexanone (10.0 g). (5) A suspension of methoxymethyltriphenylphosphonium chloride (11.3 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium -t-butoxide (4.1 g) little by little while cooling at 0°C, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(2'-(3'',4'',5''-trifluoro-4'''-biphenyl)ethyl)cyclohexanone (10.0 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature, further stirring the mixture for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (200 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 4-(2'-(3'',4'',5''-trifluoro-4'''-biphenyl)ethyl)methoxymethylenecyclohexane (7.5 g). (6) THF (50 ml) and 2N hydrochloric acid (50 ml) were added to 4-(2'-(3'',4'',5''-trifluoro-4'''-biphenyl)ethyl)methoxymethylenecyclohexane (7.5 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , and concentrating under reduced pressure, to obtain 4-(2'-(3'',4'',5''-trifluoro-4'''-biphenyl)ethyl)cyclohexylcarbaldehyde (5.8 g). (7) A suspension of methyltriphenylphosphonium bromide (7.2 g) in THF (20 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (1.6 g) little by little while cooling at 0°C, stirring the resulting reaction solution at room temperature for one hour, dropwise adding a solution of 4-(2'-(3'',4'',5''-trifluoro-4'''-biphenyl)ethyl)cyclohexanecarbaldehyde (5.8 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO 4 , concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5) and recrystallizing from heptane, to obtain 2-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenyl)ethyl)cyclohexyl)ethene (3.5 g). The following compounds are prepared by repeating the above-mentioned carbon number-increasing reactions: 482. 3-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-1-propene 483. 3-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-2E-propene 484. 4-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-1-butene 485. 4-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-2E-butene 486. 4-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-3E-butene 487. 5-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-1-pentene 488. 5-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-2E-pentene 489. 5-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-3E-pentene 490. 5-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-4E-pentene 491. 6-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-1-hexene 492. 6-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-2E-hexene 493. 6-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-3E-hexene 494. 6-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-4E-hexene 495. 7-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-2E-heptene 496. 7-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-3E-heptene 497. 7-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-4E-heptene 498. 8-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-3E-octene 499. 8-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-4E-octene 500. 9-(4'-trans-(2''-(3''',4''',5'''-trifluoro-4'''-biphenylyl)ethyl)cyclohexyl)-4E-nonene 501. 2-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)ethene 502. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-2E-propene 503. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-1-propene 504. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoro'ethyl-4'''-biphenylyl)ethyl)cyclohexyl)-1-butene 505. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-2E-butene 506. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-3E-butene 507. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-1-pentene 508. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-2E-pentene 509. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoronethyl-4'''-biphenylyl)ethyl)cyclohexyl)-3E-pentene 510. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoronethyl-4'''-biphenylyl)ethyl)cyclohexyl)-4E-pentene 511. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-1-hexene 512. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-2E-hexene 513. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-3E-hexene 514. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-4E-hexene 515. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-2E-heptene 516. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluorcmethyl-4'''-biphenylyl)ethyl)cyclohexyl)-3E-heptene 517. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-4E-heptene 518. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-3E-octene 519. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-4E-octene 520. 9-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethyl-4'''-biphenylyl)ethyl)cyclohexyl)-4E-nonene 521. 2-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)ethene 522. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-2E-propene 523. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-1-propene 524. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-1-butene 525. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-2E-butene 526. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-3E-butene 527. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-1-pentene 528. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-2E-pentene 529. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-3E-pentene 530. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-4E-pentene 531. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoronethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-1-hexene 532. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoronethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-2E-hexene 533. 6-(4'-trans(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-3E-hexene 534. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-4E-hexene 535. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-2E-heptene 536. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-3E-heptene 537. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-4E-heptene 538. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-3E-octene 539. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-4E-octene 540. 9-(4'-trans-(2''-(3''',5'''-difluoro-4'''-trifluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-4E-nonene 541. 2-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)ethene 542. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-2E-propene 543. 3-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-1-propene 544. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-1-butene 545. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-2E-butene 546. 4-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-3E-butene 547. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-1-pentene 548. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-2E-pentene 549. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-3E-pentene 550. 5-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-4E-pentene 551. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-1-hexene 552. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-2E-hexene 553. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-3E-hexene 554. 6-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-4E-hexene 555. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-2E-heptene 556. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-3E-heptene 557. 7-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-4E-heptene 558. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-3E-octene 559. 8-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-4E-octene 560. 9-(4'-trans-(2''-(3''',5'''-difluoro-4'''-difluoromethoxy-4'''-biphenylyl)ethyl)cyclohexyl)-4E-nonene Application example 1 A compound of the present invention (15 parts by weight) shown in Example 1 was added to a composition A consisting of The resulting liquid crystal composition exhibited an NI point of -95.6°C when extrapolated, and a viscosity at 20°C of 2.3 cp. This liquid crystal composition was sealed in a TN cell of 8.7 µm thick, and its threshold voltage was observed to give 1.28 V. Its elastic constant of K 33 /K 11 , was 1.99 and that of K 33 /K 22 was 2.69. As a comparative example, a comparative compound (B) expressed by the formula, (15 parts by weight) was added to the composition (A) (85 parts by weight). The resulting liquid crystal composition exhibited a NI point of -59.6°C when extrapolated, and a viscosity at 20°C of -1.0 cp. Further, this liquid crystal composition was sealed in a TN cell of 8.7 µm thick, and its threshold voltage was observed to give 1.44 V. Its elastic constant of K 33 /K 11 was 1.74 and that of K 33 /K 22 was 2.07. Application example 2 A compound of the present invention shown in Example 2 (15 parts by weight) was added to the composition A used in Application example 1 (85 parts by weight). The resulting liquid crystal composition exhibited an NI point of -119.6°C when extrapolated. When the composition was filled in a TN cell of 8.7 µm thick and the threshold voltage was observed to give 1.15 V. The elastic constant of K 33 /K 11 was 1.77 and that of K 33 /K 22 was 2.53. Application example 3 A compound of the present invention shown in Example 4 (15 parts by weight) was added to the composition A used in Application example 1. The resulting liquid crystal composition exhibited an NI point of 57.1°C and a viscosity at 20°C of 31.0 cp. This liquid crystal composition was filled in a TN cell of 8.7 µm thick and the threshold voltage was observed to give 1.55 V. The elastic constant of K 33 /K 11 was 2.00 and that of K 33 /K 22 was 2.93. As a comparative example, a comparative compound (C) expressed by the formula (15 parts by weight) was added to the composition A used in Application example 1 (85 parts by weight). The liquid crystal composition exhibited an NI point of 47.7°C when extrapolated and a viscosity at 20°C of 30.3 cp. This liquid crystal composition was filled in a TN cell of 8.8 µm thick and the threshold voltage was observed to give 1.48 V. The elastic constant of K 33 /K 11 was 2.11 and that of K 33 /K 22 was 2.86. Application example 4 A compound of the present invention shown in Example 3 (15 parts by weight) was added to the composition A used in Application example 1 (85 parts by weight). The resulting liquid crystal composition exhibited an NI point of -133.6°C when extrapolated. Further, this liquid crystal composition was filled in a TN cell of 8.7 µm thick and the threshold voltage was observed to give 1.00 V. Application example 5 A compound of the present invention shown as compound No. 84 (15 parts by weight) was added to the composition A used in Application example 1 (85 parts by weight). The resulting liquid crystal composition exhibited an NI point of 79.1°C when extrapolated and a viscosity at 20°C of 29.0 cp. This liquid crystal composition was filled in a TN cell of 8.6 µm thick and the threshold voltage was observed to give 1.63 V. Effectiveness of the Invention The compound provided by the present invention has a low viscosity and when the compound is added, it is possible to lower the threshold voltage of the resulting display element.

Claims: A compound expressed by the formula (I) wherein X represents a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a difluoromethoxy group, -A- represents 1,4-cyclohexylene or 1,4-phenylene, -B- represents 1,4-cyclohexylene, l represents 0, 1 or 2, m represents 0, 1 or 2, and 1+m≧1, Z represents -CH 2 CH 2 - or a single bond, n represents an integer of 0 to 4, R represents a hydrogen atom or a linear or branched alkyl group of 1 to 7 carbon atoms, and when R represents an alkyl group, the double bond has a trans-configuration. A compound according to claim 1, wherein -A- represents 1,4-cyclohexylene, l represents 1, m represents 0 and Z represents a single bond. A compound according to claim 1, wherein -A- represents 1,4-cyclohexylene, l represents 2, m represents 0 and Z represents a single bond. A compound according to claim 1, wherein l represents 0, m represents 1 and Z represents -CH 2 CH 2 -. A compound according to claim 1, wherein -A- represents 1,4-cyclohexylene, l represents 1, m represents 1 and Z represents -CH 2 CH 2 -. A compound according to claim 1, wherein -B- represents 1,4-cyclohexylene, l represents 0, m represents 2 and Z represents-CH 2 CH 2 -. A compound according to claim 1, wherein -A- represents 1,4-phenylene, l represents 1, m represents 1 and Z represents a single bond. A compound according to claim 1, wherein -A- represents 1,4-phenylene, l represents 1, m represents 1 and Z represents -CH 2 CH 2 -. A liquid crystal composition comprising at least one liquid crystalline compound and at least one compound expressed by the formula (I) wherein X represents a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a difluoromethoxy group, -A- represents 1,4-cyclohexylene or 1,4-phenylene, -B- represents 1,4-cyclohexylene, l represents 0, 1 or 2, m represents 0, 1 or 2 and 1+m≧1, Z represents -CH 2 CH 2 - or a single bond, n represents an integer of 0 to 4, R represents a hydrogen atom or a linear or branched alkyl group of 1 to 7 carbon atoms, and when R represents an alkyl group, the double bond has a trans-configuration.

Inventors: GOTO YASUYUKI, KONDO TOMOYUKI, MATSUI SHUICHI, ONJI YUICHI, USHIODA MAKOTO, GOTO, YASUYUKI, KONDO, TOMOYUKI, MATSUI, SHUICHI, ONJI, YUICHI, USHIODA, MAKOTO
Applicants: CHISSO CORP, CHISSO CORPORATION
Application year: 1993
Main classification: C09K19
IPC codes: C07C45, C07C17, C07C43, C09K19, C07C25