| a,a-二(2-羟乙基)苯乙腈分子内环合现象的核磁共振研究 |
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| 引用本文： | 高振华,何小伟,郭永彪,邹传品.a,a-二(2-羟乙基)苯乙腈分子内环合现象的核磁共振研究[J].波谱学杂志,2014,31(2):284-294. |
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| 作者姓名： | 高振华 何小伟 郭永彪 邹传品 |
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| 作者单位： | 北京药物化学研究所，北京 102205 |
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| 摘 要： | 以苯乙腈为原料，在二异丙基氨基锂(LDA)的作用下连续与两分子环氧乙烷反应，一步合成a,a-二(2-羟乙基)苯乙腈(2a)．通过对1H NMR、13C NMR、DEPT、HSQC、HMBC等谱图的解析，证明此类化合物存在因分子内环合所致的互变异构现象．该现象可用于解释使用化合物2a为原料，甲磺酰化后再与伯胺反应生成哌啶衍生物产率低下的原因．
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| 关 键 词： | 核磁共振(NMR) 结构解析 D NMR α α-二(-羟乙基)苯乙腈 互变异构 |
| 收稿时间： | 2014-02-21 |
The NMR Study on the Intramolecular Cyclization ofa,a-Bis(2-Hydroxyethyl)phenylacetonitrile |
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| GAO Zhen-hua,HE Xiao-wei,GUO Yong-biao,ZOU Chuan-pin.The NMR Study on the Intramolecular Cyclization ofa,a-Bis(2-Hydroxyethyl)phenylacetonitrile[J].Chinese Journal of Magnetic Resonance,2014,31(2):284-294. |
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| Authors: | GAO Zhen-hua HE Xiao-wei GUO Yong-biao ZOU Chuan-pin |
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| Abstract: | a, a-Bis(2-hydroxyethyl)phenylacetonitrile (2a) was efficiently synthesized from phenylacetonitrile, lithium diisopropylamide and ethylene oxide by one-pot method. Through the analysis with 1H NMR, 13C NMR, DEPT, HSQC, HMBC spectra, it has proved that there is a tautomerism caused by intramolecular cyclization. This phenomena can be used to explain the low yield of piperidine derivatives synthesized from compounds 2avia mesylation and cyclization. |
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