Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (12): 1612-1617. Previous Articles    

Reports

左旋异松蒎酮的合成

王石发*,李艳苹,张明光   

  1. (南京林业大学化学工程学院 南京 210037)
  • 收稿日期:2007-08-04 修回日期:2007-10-17 发布日期:2007-12-04
  • 通讯作者: 王石发

Synthesis of (-)-Isopinocamphone

WANG Shi-Fa*, LI Yan-Ping, ZHANG Ming-Guang   

  1. (College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037)
  • Received:2007-08-04 Revised:2007-10-17 Published:2007-12-04
  • Contact: WANG Shi-Fa

Synthesis of (-)-isopinocamphone was carried out using (-)-α-pinene as the starting material. Borane obtained from the reaction of NaBH4 and BF3•(C2H5)2O without purification was directly re-acted with α-pinene in THF to obtain diisopinocampheylborane, which was further oxidized with so-dium perborate tetrahydrate to afford isopinocampheol as white solids, in a yield 89.5%, purity 97.4%, m.p. 55~56 ℃, +28.31 (c 5.55, CH3OH). Isopinocamphone was prepared by oxidiz-ing isopinocampheol with hydrogen peroxide under catalysis of vanadium phosphorus oxide, in a yield over 88%, purity 96.0%, -10.58 (c 5.51, CH3OH). The structures of isopinocampheol and isopinocamphone were determined by IR, 1H NMR, 13C NMR and MS spec-tra.

Key words: (+)-isopinocampheol, (-)-isopinocamphone, (-)-α-pinene