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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (02): 246-248. 上一篇    下一篇

研究简报

邻硝基酚醚上的异常取代反应

张裴，童元峰，王冬梅，吴松*   

  1. (中国医学科学院北京协和医学院药物研究所 卫生部天然药物生物合成重点实验室 北京 100050)
  • 收稿日期:2010-05-11 修回日期:2010-08-30 发布日期:2010-10-08
  • 通讯作者: 张裴 E-mail:sophysea@163.com
  • 基金资助:

    “重大新药创制”科技重大专项;国家自然科学基金青年科学基金

Unexpected Substitution of Alkyloxy-nitrobenzene

ZHANG Pei, TONG Yuan-Feng, WANG Dong-Mei, WU Song   

  1. (Key Laboratory of Biosynthesis of Natural Products, Ministry of Health of PRC, Chinese Academy of Medical Sciences & Peking Union Medical College, Institute of Materia Medica, Beijing 100050)
  • Received:2010-05-11 Revised:2010-08-30 Published:2010-10-08

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被引次数

1

以2-(2-硝基苯氧基)-1-溴乙烷或3-(2-硝基苯氧基)-1-溴丙烷为原料分别在氢化钠作用下与N-Boc-4-羟基哌啶反应, 得到了与预期结构不同的产物. 该产物的结构经1H NMR, 13C NMR, LC-MS分析表明, 其并非为原料2-(2-硝基苯氧基)-1-溴乙烷与N-Boc-4-羟基哌啶发生Williamson反应生成预期的混合醚, 而是芳环上的烷氧基被取代的异常产物. 根据这个实验结果, 推测上述反应的可能机理是发生了芳环上的亲核取代反应.

关键词: 2-(2-硝基苯氧基)-1-溴乙烷, N-Boc-4-羟基哌啶, 异常产物, 反应机理

The unexpected product from reaction of 2-(2-nitrophenoxy)-1-bromoethane or 3-(2-nitrophenoxy)-1-bromopropane with N-Boc-4-hydroxypiperidine was obtained and the data of 1H NMR, 13C NMR and LC-MS of the product indicated that no Williamson reaction happened, instead, the alkyloxy in alkyloxy-nitrobenzene was substituted by N-Boc-4-hydroxypiperidine. Based on the fact, possible mechanism of the reaction was discussed.

Key words: 2-(2-nitrophenoxy)-1-bromoethane, N-Boc-4-hydroxypiperidine, unexpected product, mechanism