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2012 >Issue 03: 520 - 525

DOI: https://doi.org/10.6023/cjoc1112031

研究论文

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

  • 陈晓东 ,
  • 叶姣 ,
  • 胡艾希
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  • 湖南大学化学化工学院 长沙 410082

收稿日期: 2011-12-03

  修回日期: 2012-01-05

  网络出版日期: 2012-03-24

基金资助

国家科技支撑计划(No. 2011 BAE06B01)资助项目.

收起

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

  • Chen Xiaodong ,
  • Ye Jiao ,
  • Hu Aixi
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  • College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received date: 2011-12-03

  Revised date: 2012-01-05

  Online published: 2012-03-24

Supported by

Project supported by the National Science & Technology Pillar Program of China (No. 2011 BAE06B01).

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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.

关键词： 鱼藤酮; 氧硫叶立德; 贝克曼重排; 晶体结构

本文引用格式

陈晓东 , 叶姣 , 胡艾希 . 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[J]. 有机化学, 2012 , (03) : 520 -525 . DOI: 10.6023/cjoc1112031

Abstract

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/cm3, μ(Mo Kα)＝0.092 mm-1, F(000)＝464.

Key words： rotenone; dimethyloxosulphonium methylide; Beckmann rearrangement; crystallographic structure

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