1,2-二氧杂环戊烷

1,2-二氧杂环戊烷，别名1,2-二氧戊环、1,2-二氧五环等，是一种化合物，分子式为C3H6O2，由三个碳原子和相邻位置的两个氧原子组成的环组成。其结构式可写为[–(CH2)3–O–O–]。 该化合物是一种有机过氧化物，特别是内过氧化物，是更常见的1,3-二氧戊环的结构异构体。 1,2-二氧戊环核心结构的合成方法包括用单线态氧或分子氧与合适的催化剂氧化环丙烷衍生物、使用自动氧化、过氧化氢进行亲核置换，并用硝酸汞处理、扩展π-系统的光解、双甲硅烷基过氧化物与烯烃的反应，或与2-过羟基4-烯烃与二乙胺或乙酸汞的反应。 一些衍生物存在于自然界，例如在Calophyllum dispar和马米杏的种子。Plakinic acid A和类似化合物是从Plakortis的海绵中分离出来的。甘松新酮是一种含有1,2-二氧戊环的倍半萜衍生物，从名为Adenosma caeruleum的植物中分离出来。 合成和天然的二氧戊环衍生物已被用作或被认为是抗疟药。Plakinic acid A和相关化合物显示出抗真菌作用。 1,2-二𫫇烷 1,2-二氧杂环丁烷 1,2-二硫戊环 Lay TH, Bozzelli JW. Enthalpies of formation of cyclic alkyl peroxides: Dioxirane, 1,2-dioxetane, 1,2-dioxolane, and 1,2-dioxane. Chemical Physics Letters. 199, 268 (1–2): 175–179. Bibcode:1997CPL...268..175L. doi:10.1016/S0009-2614(97)00168-1.  Demaison J. 2.5.2.5 Elements with two or three internal rotors. Diamagnetic Molecules. Landolt-Börnstein - Group II Molecules and Radicals 14a. 1982: 415–425. ISBN 3-540-11365-7. doi:10.1007/10201404_40.  Akasaka T, Fukuoka K, Ando W. Formation of 1,2-dioxolane in the singlet oxygenation of cyclopropane. Tetrahedron Letters. 1991, 32 (52): 7695–7698. doi:10.1016/0040-4039(91)80568-Q.  Feldman KS, Simpson RE. Stereochemical studies on the preparation and subsequent reductive cleavage of 1,2-dioxolanes. Application to the synthesis of (±)-yashabushitriol. Tetrahedron Letters. 1989, 30 (50): 6985–6988. doi:10.1016/S0040-4039(01)93404-5.  Mata S, González J, Vicente R, López LA. Zinc-Catalyzed Multicomponent Reactions: Easy Access to Furyl-Substituted Cyclopropane and 1,2-Dioxolane Derivatives (PDF). European Journal of Organic Chemistry. 2016, 2016 (15): 2681–2687 [2023-04-26]. doi:10.1002/ejoc.201600393. （原始内容存档 (PDF)于2023-04-26）.  Helesbeux JJ, Peyronnet D, Labaïed M, Grellier P, Frappier F, Seraphin D, et al. Synthesis and antimalarial activity of some new 1,2-dioxolane derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry. December 2002, 17 (6): 431–7. PMID 12683680. doi:10.1080/1475636021000005677 .  Martyn DC, Ramirez AP, Beattie MJ, Cortese JF, Patel V, Rush MA, et al. Synthesis of spiro-1,2-dioxolanes and their activity against Plasmodium falciparum. Bioorganic & Medicinal Chemistry Letters. December 2008, 18 (24): 6521–4. PMID 18993067. doi:10.1016/j.bmcl.2008.10.083.  Liu HH, Jin HX, Wu YK. Synthesis and cleavage studies of a 1,2-dioxolane-type peroxide. Chinese Journal of Chemistry. 2010, 22 (9): 1029–1033. doi:10.1002/cjoc.20040220930.  Booldworth AJ, Tallant NA. 1,2,4-Trioxane versus 1,2-dioxolane formation in the mercury(II) acetate-mediated cyclisation of hemiperoxyacetals derived from allylic hydroperoxides. Journal of the Chemical Society, Chemical Communications. 1992, (5): 428. doi:10.1039/C39920000428.  Bloodworth AJ, Bothwell BD, Collins AN, Maidwell NL. A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group. Tetrahedron Letters. 1996, 37 (11): 1885–1888. doi:10.1016/0040-4039(96)00143-8.  Phillipson DW, Rinehart Jr K. Antifungal peroxide-containing acids from two Caribbean sponges. Journal of the American Chemical Society. 1983, 105 (26): 7735–7736. doi:10.1021/ja00364a045.  Dai P, Trullinger TK, Liu X, Dussault PH. Asymmetric synthesis of 1,2-dioxolane-3-acetic acids: synthesis and configurational assignment of plakinic acid A. The Journal of Organic Chemistry. March 2006, 71 (6): 2283–92. PMID 16526775. doi:10.1021/jo0522254.  Kandur WV, Richert KJ, Rieder CJ, Thomas AM, Hu C, Ziller JW, Woerpel KA. Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones. Organic Letters. May 2014, 16 (10): 2650–3. PMID 24779430. doi:10.1021/ol500835f.