Chin. J. Org. Chem. ›› 2012, Vol. ›› Issue (03): 520-525.DOI: 10.6023/cjoc1112031 Previous Articles     Next Articles



陈晓东, 叶姣, 胡艾希   

  1. 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 发布日期:2012-03-24
  • 通讯作者: 胡艾希
  • 基金资助:

    国家科技支撑计划(No. 2011 BAE06B01)资助项目.

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   

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
  • Received:2011-12-03 Revised:2012-01-05 Published:2012-03-24
  • Supported by:

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

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