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Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (12): 1612-1617. Previous Articles
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王石发*,李艳苹,张明光
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WANG Shi-Fa*, LI Yan-Ping, ZHANG Ming-Guang
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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
WANG Shi-Fa*, LI Yan-Ping, ZHANG Ming-Guang. Synthesis of (-)-Isopinocamphone[J]. Chin. J. Org. Chem., 2007, 27(12): 1612-1617.
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