摘要
鱼藤酮与氧硫叶立德反应得到关键中间体(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基)[(R)-4-羟基-2-(丙烯-2-基)-2,3-二氢苯并呋喃-5-基]甲酮(2),2再通过醚化、肟化、贝克曼重排得到5,6-二甲氧基-N-[(R)-4-甲氧基-2-(丙烯-2-基)-2,3-二氢苯并呋喃-5-基]-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基甲酰胺(5),化合物的结构经1H NMR,MS和元素分析确认,采用单晶X射线衍射法确定化合物5的晶体结构.化合物5属于三斜晶系,P1空间群,晶胞参数:a=0.95772(5)nm,b=1.06591(6)nm,c=1.30112(7)nm,α=111.8460(10)°,β=109.8870(10)°,γ=93.0870°,V=1.13429(11)nm3,Z=2,Dc=1.281 g/cm3,μ(Mo Kα)=0.092 mm-1,F(000)=464.
5,6-Dimethoxy-N-[(R)-4-methoxy-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-yl]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-7b-carboxamide(5) was prepared by etherification,oximation and Beckmann rearrangement from 5,6-dimethoxy-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7b-yl((R)-4-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-yl)-methanone(2) which synthesized from the reaction of the rotenone and dimethyloxosulphonium methylide.Their structures were identified by 1H NMR and MS techniques and elemental analysis.The crystal structures of compounds 2 and 5 were determined by X-ray single crystal diffraction analysis.The crystal of 5 belongs to triclinic,space group P1 with cell parameters a=0.95772(5) nm,b=1.06591(6) nm,c=1.30112(7) nm,α=111.8460(10)°,β=109.8870(10)°,γ=93.0870°,V=1.13429(11) nm3,Z=2,Dc= 1.281 g/cm^3,μ(Mo Kα)=0.092 mm^-1,F(000)=464.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2012年第3期520-525,共6页
Chinese Journal of Organic Chemistry
基金
国家科技支撑计划(No.2011 BAE06B01)资助项目~~
关键词
鱼藤酮
氧硫叶立德
贝克曼重排
晶体结构
rotenone
dimethyloxosulphonium methylide
Beckmann rearrangement
crystallographic structure