基于消除-加成机理的β-氨基-β-芳基丙烯醛新合成方法研究  

Synthesis of β-Amino-β-arylacroleins Based on Elimination-addition Mechanism

作　　者：秦剑 刘雨风 居辰阳 李飞龙[1] 赵敏[1] 陈建中[2] QIN Jian;LIU Yu-feng;JU Chen-yang;LI Fei-long;ZHAO Min;CHEN Jian-zhong(School of Chemistry and Molecular Engineering,East China University of Sci- ence and Technology, Shanghai 200237, China;School of Chemistry and Chemical Engineering, Shanghai Jiaotong University, Shanghai 200240, China)

机构地区：[1]华东理工大学化学与分子工程学院,上海200237 [2]上海交通大学化学化工学院,上海200240

出　　处：《化学试剂》2017年第12期1275-1281,1288,共8页Chemical Reagents

基　　金：上海市科委基金资助项目(17ZR1415200)

摘　　要：研究了α-溴代肉桂醛与苯酚的具体反应过程,证明了其先消除再加成的反应机理,进而将该反应应用于β-芳基丙烯醛的β-位含氮基团官能化反应中。通过易得的α-溴代肉桂醛与邻苯二甲酰亚胺钾盐反应,得到一系列β-含氮官能团芳基丙烯醛,所得产物结构经1HNMR、13CNMR、ESI-MS和IR等表征,构型经X-射线单晶衍射确定。β-芳基丙烯醛官能化产物经简单转化即可应用于药物和天然产物的合成中。An elimination-addition pathway for the reaction of α-bromo-β-arylacroleins with phenol has been elucidated.β-Amino-β-arylacroleins have been prepared according to this reaction mechanism.The α-bromo-β-arylacroleins were obtained via bromination with bromine water. The corresponding β-（1,3-dioxoisoindolin-2-yl）-β-arylacroleins were subsequently prepared with good yields in the presence of potassium 1,3-dioxoisoindolin-2-ide in DMF.The structures were confirmed by1 HNMR,13 CNMR,ESIMS,IR and X-ray.The β-substituted-β-arylacrylaldehydes could be used for the synthesis of drugs and bioactive compounds.

关 键 词：消除-加成机理 α-溴代肉桂醛 β-氨基-β-芳基丙烯醛 药物合成 

分 类 号：O625[理学—有机化学] O622.6[理学—化学]