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Chinese Journal of Organic Chemistry >

2012 >Issue 03: 520 - 525

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

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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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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

Cite this article

Chen Xiaodong , Ye Jiao , Hu Aixi . 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[J]. Chinese Journal of Organic Chemistry, 2012 , (03) : 520 -525 . DOI: 10.6023/cjoc1112031

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