路易斯酸促进异构化/消除一锅合成反式-4-苯基-3-丁烯酸乙酯  

Lewis acid-promoted isomerization/elimination of one-pot synthesis of ethyl (E)-4-phenylbut-3-enoate

作　　者：李全睿 张胜[1] 包明[1,2] LI Quan-rui;ZHANG Sheng;BAO Ming(State Key Laboratory of Fine Chemicals,Dalian University of Technology,Dalian 116023,China;School of Petroleum and Chemical Engineering,Dalian University of Technology,Panjin 124221,China)

机构地区：[1]大连理工大学精细化工国家重点实验室,辽宁大连116023 [2]大连理工大学石油与化学工程学院,辽宁盘锦124221

出　　处：《分子科学学报》2020年第5期353-360,I0001,共9页Journal of Molecular Science

基　　金：国家自然科学基金青年基金资助项目(21602026);中央高校基本科研业务费专项资金资助项目(DUT18RC(4)043)。

摘　　要：使用2-苯基环丙烷-1,1-二羧酸二乙酯及其衍生物为底物,通过路易斯酸促进的环丙烷异构化/消除串联策略一锅法合成了一系列反式-4-苯基-3-丁烯酸乙酯类化合物.结果表明:以无水氯化铝(AlCl3)为添加剂,N,N-二甲基甲酰胺为溶剂,130℃下反应12 h后,以高收率和高选择性得到一系列反式-4-苯基-3-丁烯酸乙酯类化合物,产率在60%~75%之间.该反应条件温和、底物适用性广,官能团兼容性较好.In this paper, a series of(E)-4-phenylbut-3-enoate compounds were synthesized by one-pot method using diethyl 2-phenylcyclopropane-1,1-dicarboxylate and its derivatives via Lewis acid-promoted tandem isomerization/elimination. The reaction of diethyl 2-phenylcyclopropane-1,1-dicarboxylate were performed in the presence of AlCl3, using DMF as solvent at 130 ℃ for 12 h. A series of(E)-4-phenylbut-3-enoate compounds were obtained with high yield and high selectivity. The yield was between 60% to 75%. This new type of reaction is operationally simple and exhibits high functional-group tolerance. Various synthetically useful functional groups.

关 键 词：反式-4-苯基-2-丁烯酸乙酯 路易斯酸促进 一锅法 异构化 消除反应 

分 类 号：O625[理学—有机化学]