| 邻硝基酚醚上的异常取代反应 |
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| 引用本文： | 张裴,童元峰,王冬梅,吴松. 邻硝基酚醚上的异常取代反应[J]. 有机化学, 2011, 31(2) |
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| 作者姓名： | 张裴 童元峰 王冬梅 吴松 |
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| 作者单位： | 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 |
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| 基金项目： | 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 |
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| 摘 要： | 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.
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| 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 |
Unexpected Substitution of Alkyloxy-nitrobenzene |
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| Zhang Pei,Tong Yuanfeng,Wang Dongmei,Wu Song. Unexpected Substitution of Alkyloxy-nitrobenzene[J]. Chinese Journal of Organic Chemistry, 2011, 31(2) |
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| Authors: | Zhang Pei Tong Yuanfeng Wang Dongmei Wu Song |
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| Affiliation: | Zhang,Pei Tong,Yuanfeng Wang,Dongmei Wu,Song*(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) |
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| Abstract: | The unexpected product from reaction of 2-(2-nitrophenoxy)-1-bromoethane or 3-(2-nitro-phenoxy)-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. |
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| Keywords: | 2-(2-nitrophenoxy)-1-bromoethane N-Boc-4-hydroxypiperidine unexpected product mechanism |
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