摘要
通过２－甲基吡啶的烷基化、部分还原、Ｈｏｆｆｍａｎ消除开环，立体选择性地合成了马尾松毛虫性信息素的前体Ｎ，Ｎ－二甲基－［２Ｚ，４Ｅ］－壬二烯胺，其全合成的总化学产率为２５．４％，异构体纯度高达９２．０％。并分析了ＮａＢＨ４还原２－烷塞吡定的机理。
This paper reports a new synthetic route for thederivatives of(Z,E)conjugated diene with highstereoselectivity.The metalation and alkylation of picoline gave 2-n-butylpyridine(Ⅲ)which was thenreduced partly by NaBH4 to give N-methyl-2-nbutyl-1, 2, 5, 6-tetrahydropyridine(V).After Hoffman elimination,N,N-dimethyl-(2Z,4E)-nonadienamine(Ⅱ),the precursor of the sex pheromone ofpine-caterpillar,was obtained in 25 .4 % chemistryyield and 92.0% e.e.(Ⅲ),(Ⅴ),(Ⅱ)are newcompounds.The possible mechanism of the reductionprocess of 2-substituted pyridine was also suggested.
出处
《化学试剂》
CAS
CSCD
北大核心
1995年第6期335-338,共4页
Chemical Reagents
关键词
合成
二甲基
壬二烯胺
昆虫信息素
N, N-Dimethyl-(2Z, 4E)-nonadienamine, 2-n-butylpyridine, N-methyl-2-n-butyl-1, 2,5,6-tetrahydropyridine, synthesis
