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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (12): 1612-1617. 上一篇    

研究简报

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

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1491

被引次数

15 | 7

研究了以(－)-α-蒎烯为原料合成(－)-异松蒎酮的反应. 以四氢呋喃为溶剂, 硼氢化钠与三氟化硼乙醚溶液生成的硼烷不经分离直接与α-蒎烯发生反马氏加成反应, 生成二异松蒎烷基硼; 采用四水合过硼酸钠或NaOH-H2O2氧化硼氢化物得到(＋)-异松蒎醇, 产率为89.5%, 纯度97.4%, 熔点为55～56 ℃, 比旋光度 ＋28.31 (c 5.55, CH3OH). 以钒磷氧化物为催化剂、双氧水作氧化剂, 将(＋)-异松蒎醇氧化得到(－)-异松蒎酮, 产率88% 以上, 纯度96.0%, 比旋光度为 －10.58 (c 5.51, CH3OH). 采用IR, MS, 1H NMR, 13C NMR等对(＋)-异松蒎醇和(－)-异松蒎酮结构进行了表征.

关键词: α-蒎烯, (＋)-异松蒎醇, (－)-异松蒎酮

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