基于1,6-亚甲基桥[10]轮烯的多环化合物的合成  

Synthesis of Polycyclic Compound Based on 1,6-Methano[10] annulene

作　　者：陈海平[1] 刘建军[1] 曹小舟[2] 白天省[1] 左胜利[1] 

机构地区：[1]北京化工大学理学院,北京100029 [2]大庆石化公司,黑龙江大庆163714

出　　处：《合成化学》2010年第5期591-594,共4页Chinese Journal of Synthetic Chemistry

基　　金：财政部公益性行业科研专项资金资助项目(200904026)

摘　　要：1,6-亚甲基桥[10]轮烯-4-溴-3-羧酸乙酯经LiAlH4还原后再在冰水浴下与PBr3反应制得3-溴甲基-4-溴-1,6-亚甲基桥[10]轮烯(3);3与PPh3在苯中回流,然后与对甲氧基苯甲醛进行Wittig反应,再经分子内异构化制得3-(p-甲氧基苯乙烯基)-4-溴-1,6-亚甲基桥[10]轮烯(trans-5);trans-5在钯盐催化下完成分子间耦合合成了基于1,6-亚甲基桥[10]轮烯的多环化合物,其结构经NMR,IR和MS表征。3-Bromomethyl-4-bromo-1,6-methano[10] annulene（3） was prepared by the reduction of ethyl 1,6-methano[10] annulene-4-bromo-3-carboxylate with LiAlH4,then reacted with PBr3 under icewater bath.3-（p-methoxystyryl）-4-bromo-1,6-methanoannulene（trans-5） was prepared by the reaction of 3 with PPh3 in benzene,Wittig reaction with p-methoxybenzaldehyde,and then isomerization of intramolecular.Polycyclic compound based on 1,6-methano[10] annulene was synthesized by intermolecular coupling reaction of trans-5 using palladium as the catalyst.The structures were confirmed by NMR,IR and MS.

关 键 词：1 轮烯 WITTIG反应 多缩环化合物 合成 

分 类 号：O625.5[理学—有机化学]