三硫丙酮

三硫丙酮（2,2,4,4,6,6-六甲基-1,3,5-三噻烷），也称三聚硫代丙酮，是一种有机物，化学式为C 9H 18S 3，共价结构式为[–C(CH 3) 2–S–] 3。该化合物可以被看作是1,3,5-三硫雜環己烷的衍生物，即一个碳原子和硫原子交替出现的六元环，每个碳再连接两个甲基，由甲基取代所有的氢原子。 该化合物是硫代丙酮（丙烷-2-硫酮）的稳定的环状三聚物，而硫代丙酮本身是一个不稳定的化合物。相比之下，与之类似的化合物三丙酮（2,2,4,4,6,6-六甲基-1,3,5-三噁烷，氧原子代替硫原子）是不稳定的，而单体丙酮（2-丙酮）本身是稳定的。 三硫丙酮最早由欧根·鲍曼（英语：Eugen Baumann）（Eugen Baumann）和E·弗罗姆（E. Fromm）于1889年通过硫化氢与丙酮的反应而合成。在25℃、酸性、有ZnCl 2催化剂的条件下，得到的产物是60%－70%的三硫丙酮，30%－40%的2,2-丙二硫醇，以及少量的两种异构体杂质3,3,5,5,6,6-六甲基-1,2,4-三硫雜環己烷和4-巯基-2,2,4,6,6-五甲基-1,3-二硫雜環己烷。该产品也可以通过烯丙基异丙基硫醚（3-异丙硫基丙-1-烯）的热解来获得。 三硫丙酮在500－650℃和5－20 mmHg下热解产生硫丙酮，可通过−78℃的冷阱收集。 三硫丙酮存在于一些香料中。其FEMA编号为3475。 小鼠口服LD50为2.4 g/kg。 2,4,6-三甲基-1,3,5-三噻烷 六甲基环三硅氧烷（英语：Hexamethylcyclotrisiloxane），硅氧杂环之相似物 六甲基环三硅氮烷，硅氮杂环之相似物 2,2,4,4,6,6-六甲基-1,3,5-三硒-2,4,6-三锡环己烷，锡-硒杂环之相似物 TCI America (2020): "Product H1278: 2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane （页面存档备份，存于互联网档案馆）". Online catalog page, accessed on 2020-01-01. NCBI PubChem (2010): "2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane （页面存档备份，存于互联网档案馆）". Online chemical data sheet, accessed on 2020-01-01. David S. Breslow, Herman Skolnik (2009): Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 2; page 712. Volume 68 of Chemistry of Heterocyclic Compounds. ISBN 9780470188330 R. D. Lipscomb and W. H. Sharkey (1970): "Characterization and polymerization of thioacetone". Journal of Polymer Science - Part A: Polymer Chemistry, volume 8, issue 8, pages 2187–2196. doi:10.1002/pol.1970.150080826 William H. Sharkey (1979): "Polymerization through the carbon-sulfur double bond". Polymerization, series Advances in Polymer Science, volume 17, pages 73-103. doi:10.1007/3-540-07111-3_2 William J. Bailey and Hilda Chu (1965): "Synthesis of polythioacetone". ACS Polymer Preprints, volume 6, pages=145–155 Horst Bohme, Hans Pfeifer, and Erich Schneider (1942): "Dimeric thioketones". Berichte der Deutschen Chemischen Gesellschaft, volume 75B, issue 7, pages 900–909. doi:10.1002/cber.19420750722 Note: This early report mistakes the trimer for the monomer. E. J. Moran, O. D. Easterday, and B. L. Oser (1980): "Acute oral toxicity of selected flavor chemicals". Drug and Chemical Toxicology, volume 3,issue 3, pages 249-258.PMID 7449655 doi:10.3109/01480548009002221 World Health Organization (1999): "Trithioacetone[失效連結]". Online data sheet in the Evaluation of the Joint FAO/WHO Expert Committee on Food Additives (JECFA). Accessedd on 2020-01-02. G. Ohloff and I. Flament (1979): "The Role of Heteroatomic Substances in the Aroma Compounds of Foodstuffs". In Fortschritte der Chemie Organischer Naturstoffe (Progress in the Chemistry of Organic Natural Products), volume 36, pages 231-283. doi:10.1007/978-3-7091-3265-4_2 EUR-Lex (2012): "Table entry 15.009: Trithioacetone （页面存档备份，存于互联网档案馆）". In EU Regulation No. 872/2012, Document 32012R0872, Official Journal of the EU - Series L, volume 267, pages 1–161. Stuart D. Brewer and Charles P. Haber (1948): "Alkylsilazanes and Some Related Compounds". Journal of the American Chemical Society, volume 70, issue 11, pages 3888-3891. doi:10.1021/ja01191a106 B. M. Mikhova (2008), "NMR Data for Carbon-13 - C6H18Se3Sn3" in Landolt-Börnstein - Group III Condensed Matter, volume 35 Nuclear Magnetic Resonance Data, subvolume D5, Organometallic Compounds. doi:10.1007/978-3-540-74189-3_1362 Martin Dräger, Axel Blecher, Hans-Jürgen Jacobsen, Bernt Krebs (1978): "Molekül- und kristallstruktur von hexamethylcyclo-tristannaselenan [(CH 3) 2SnSe] 3". Journal of Organometallic Chemistry, volume 161, issue 3, pages 319-325. doi:10.1016/S0022-328X(00)92243-5