镍合金还原1-萘酚反应的再研究reinvestigation of the reduction of 1 .pdf

2008 年第 28 卷 有 机 化 学 Vol. 28, 2008 第 4 期, 723～726 Chinese Journal of Organic Chemistry No. 4, 723～726 ·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* (复旦大学药学院药物化学教研室 上海 200032) 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. 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 Reinvestigation of the Reduction of 1-Naphthol Using Ni-Al Alloy ZHANG, Jing-Lei WANG, Yang* (Department of Medicinal Chemistry , School of Pharmacy, Fudan University, Shanghai 200032) 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 reduc- tion of 1-naphthol using Ni-Al alloy under alkaline conditions has provided a new synthetic pathway for the preparation of 3 and 4. Keywords 1-naphthol; 3,4-dihydro-2H-naphthalen-1-one; 1,2,3,4-tetrahydro-1-naphthol; Ni-Al alloy; reduction 我们在研究抗人类免疫缺陷病毒(human immuno- 1 实验部分 deficiency virus, HIV)活性化合物的合成过程中