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，共价结构式为。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。

制备
三硫丙酮最早由（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。

反应
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。

300px|center|三硫丙酮（左）和硫丙酮（右）通过热分解/聚合可互相转化

用途
三硫丙酮存在于一些香料中。其FEMA编号为3475。

毒性
小鼠口服LD50为2.4 g/kg。

参见
 2,4,6-三甲基-1,3,5-三噻烷
 ，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

参考资料
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TCI America (2020): "Product H1278: 2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane ". Online catalog page, accessed on 2020-01-01.

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. 

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William H. Sharkey (1979): "Polymerization through the carbon-sulfur double bond". Polymerization, series Advances in Polymer Science, volume 17, pages 73-103. 

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. 

World Health Organization (1999): "Trithioacetone". Online data sheet in the Evaluation of the Joint FAO/WHO Expert Committee on Food Additives (JECFA). Accessedd on 2020-01-02.

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. 

NCBI PubChem (2010): "2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane ". Online chemical data sheet, accessed on 2020-01-01.

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. 

Category:含硫杂环
Category:六元环