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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (04): 723-726. 上一篇    下一篇

研究简报

用铝-镍合金还原1-萘酚反应的再研究

张晶蕾，王洋*   

  1. (复旦大学药学院药物化学教研室 上海 200032)
  • 收稿日期:2007-06-25 修回日期:2007-09-07 发布日期:2008-04-17
  • 通讯作者: 王洋

Reinvestigation of the Reduction of 1-Naphthol Using Ni-Al Alloy

ZHANG Jing-Lei,WANG Yang*   

  1. (Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 200032)
  • Received:2007-06-25 Revised:2007-09-07 Published:2008-04-17
  • Contact: WANG Yang

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文献曾报道以铝-镍合金为还原剂, 在稀碱水溶液中, 可以将1-萘酚(1)以高收率还原为5,6,7,8-四氢-1-萘酚(2). 本研究工作发现, 在相同的条件下该反应除了生成少量2外, 3,4-二氢-2H-萘-1-酮(3)和1,2,3,4-四氢-1-萘酚(4)为主要产物, 该结果明显不同于文献报道, 对反应产物分布及其可能机理进行了探讨. 该还原反应体系为3,4-二氢-1(2H)-萘酮(3)和1,2,3,4-四氢-1-萘酚(4)的合成提供了一条新途径.

关键词: 1-萘酚, 3,4-二氢-2H-萘-1-酮, 还原, 1,2,3,4-四氢-1-萘酚, 铝-镍合金

The reduction of 1-naphthol (1) in dilute aqueous KOH using Ni-Al alloy as a reducing agent reported in the literature gave 5,6,7,8-tetrahydro-1-naphthol (2) in a high yield. The reinvestigation of this reaction under the same experimental conditions disclosed that the major products were 3,4-dihydro-2H- naphthalen-1-one (3) and 1,2,3,4-tetrahydro-1-naphthol (4) besides the formation of 2 as the minor product. The product distribution was examined and the possible mechanism was proposed. Accordingly, the reduction of 1-naphthol using Ni-Al alloy under alkaline conditions has provided a new synthetic pathway for the preparation of 3 and 4.

Key words: 3,4-dihydro-2H-naphthalen-1-one, 1-naphthol, 1,2,3,4-tetrahydro-1-naphthol, reduc-tion, Ni-Al alloy