| 用铝-镍合金还原1-萘酚反应的再研究 |
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| 引用本文： | 张晶蕾,王洋.用铝-镍合金还原1-萘酚反应的再研究[J].有机化学,2008,28(4):723-726. |
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| 作者姓名： | 张晶蕾 王洋 |
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| 作者单位： | 复旦大学药学院药物化学教研室,上海,200032 |
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| 摘 要： | 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.
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| 关 键 词： | 1-萘酚 3 4-二氢-2H-萘-1-酮 1 2 3 4-四氢-1-萘酚 铝-镍合金 还原 |
| 收稿时间： | 2007-6-25 |
| 修稿时间： | 2007年6月25日 |
Reinvestigation of the Reduction of 1-Naphthol Using Ni-Al Alloy |
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| ZHANG Jing-Lei,WANG Yang.Reinvestigation of the Reduction of 1-Naphthol Using Ni-Al Alloy[J].Chinese Journal of Organic Chemistry,2008,28(4):723-726. |
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| Authors: | ZHANG Jing-Lei WANG Yang |
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| Institution: | (Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 200032) |
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| Abstract: | 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. |
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| Keywords: | 1-naphthol 3 4-dihydro-2H-naphthalen-1-one 1 2 3 4-tetrahydro-1-naphthol Ni-Al alloy reduc-tion |
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