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-基甲酰胺的合成与表征

Synthesis and Characterization of 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

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.