Starkenmann Christian, Brauchli Robert, Maurer Bruno
R&D Division, FIRMENICH SA, P.O. Box 239, CH-1211 Geneva 8, Switzerland.
J Agric Food Chem. 2005 Nov 16;53(23):9244-8. doi: 10.1021/jf051712h.
The reaction of beta,beta-disubstituted acroleins [3-methyl-2-butenal (1), 3-methyl-2-hexenal (2), and citral (3)] with cysteine gave 1:2 adducts of a novel structural type, namely hexahydro-1,4-thiazepines. To the best of our knowledge, the spontaneous formation of a seven-membered heterocycle from the addition of cysteine to alpha,beta-unsaturated aldehydes is unprecedented. The adduct 6 obtained from citral, under acidic conditions, reacted further to give the new bicyclic compound 8.
β,β-二取代丙烯醛[3-甲基-2-丁烯醛（1）、3-甲基-2-己烯醛（2）和柠檬醛（3）]与半胱氨酸反应生成了新型结构的1:2加合物，即六氢-1,4-硫氮杂䓬。据我们所知，半胱氨酸与α,β-不饱和醛加成自发形成七元杂环是前所未有的。柠檬醛得到的加合物6在酸性条件下进一步反应生成新的双环化合物8。
