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一种多取代硝基环丙烷的开环反应研究
引用本文:宣宜宁,刘畅,周玉平.一种多取代硝基环丙烷的开环反应研究[J].广州化学,2014(2):33-36.
作者姓名:宣宜宁  刘畅  周玉平
作者单位:广东药学院药科学院,广东广州510006
摘    要:以一种多取代硝基环丙烷为底物,研究其在不同条件下的开环反应.以苄胺为亲核试剂时,底物发生开环生成烯胺化合物,对此反应机理进行了分析.研究了底物的还原开环反应:1)在Pd/C的催化氢化下,底物发生开环并消除硝基,得到烷基取代丙二酸二甲酯衍生物;2)在浓盐酸存在下用锌粉还原底物,得到五元环内酰胺.

关 键 词:硝基环丙烷  开环反应  催化氢化

Study on the Ring-opening Reactions of a Polysubstituted Nitrocyclopropane
XUAN Yi-ning,LIU Chang,ZHOU Yu-ping.Study on the Ring-opening Reactions of a Polysubstituted Nitrocyclopropane[J].Guangzhou Chemistry,2014(2):33-36.
Authors:XUAN Yi-ning  LIU Chang  ZHOU Yu-ping
Institution:(College of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China)
Abstract:Ring-opening reactions of a polysubstituted nitrocyclopropane under different conditions was studied. When the benzyl amine was used as nucleophile, ring-opening reaction of the substrate occurred and an enamine compound was obtained. The mechanism for the reaction was analyzed. The reductive ring-opening reaction of the substrate was also investigated: 1) By Pd/C catalytic hydrogenation, an aikyl-substituted dimethyl malonate derivative was obtained via nitro elimination and ring-opening of the substrate. 2) In the presence of concentrated hydrochloric acid, a lactam with a five-membered ring was acquired by reducing the cyclopropane with Zinc dust.
Keywords:nitrocyclopropane  ring-opening reaction  catalytic hydrogenation
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