5-L-孟氧基-4-苄氨基丁烯内酯的不对称合成和晶体结构研究

摘要

The novel chiral 5-(L)-menthyloxy(1R,2S,5R)-4-benzylamine-butenolide (C21H29NO3) is synthesized by Michael addition / internal elimination reaction of 5-(L)-menthyloxy-3- bromo -2(5H)-furanone with benzylamine under mild condition,and its structure is determined by X-ray diffraction. The title chiral compound belongs to orthorhombic,space group P212121 with a=5.2945(4),b=14.2829(10),c=26.0769(18)(A),Mr=343.45,Z=4,V=1972.0(2)(A)3,Dc = 1.157 g/cm3,μ(MoKα)=0.076 mm-1,F(000)=744,R=0.0387 and wR=0.0880.%温和条件下,苄胺与手性合成子5-(L)-孟氧基3-溴-2(5)呋喃酮通过串联的不对称迈克尔加成/分子内消除反应合成了一种新手性化合物:5-L-孟氧基-4-苄胺基丁烯内酯.产物经过IR 、1H-NMR 、MS谱学表征,并经X-ray单晶衍射测定了其结构.新化合物属于正交晶系,P212121 空间群,a=5.2945(4),b=14.2829(10),c=26.0769(18) ,Mr=343.45,Z=4,V=1972.0(2) 3,Dc = 1.157 g/cm3,μ(MoKα)=0.076 mm-1,F(000)=744,R=0.0387 ,wR=0.0880.