表面活性剂介入酵母细胞催化芳香酮的对映选择性还原
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Enantioselective reduction of aromatic ketones catalyzed by yeast cells in the presence of surfactants
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    摘要:

    以酵母细胞催化4’-氯苯乙酮合成(S)-1-4’-氯苯基乙醇为模型反应,研究了十六烷基三甲基溴化铵、十二烷基硫酸钠和壬基酚聚氧乙烯醚系列表面活性剂对酵母细胞催化4’-氯苯乙酮对映选择性还原反应的影响。结果表明向反应体系中加入表面活性剂可明显提高4’-氯苯乙酮的转化率,而对产物(S)-1-4’-氯苯基乙醇对映体过量值的影响极小,壬基酚四聚氧乙烯醚(NP-4)是最合适的添加剂。此外还考察了NP-4对酵母细胞催化系列芳香酮对映选择性还原反应的影响,结果表明NP-4对产物(S)-1-芳基乙醇的对映体过量值几乎没影响,但对底物芳香酮转化率均有明显的提高,同时还发现底物转化率的提高幅度与芳香环上取代基的电子效应有关,取代基供电子能力越强越有利于底物转化率的增加。

    Abstract:

    In aqueous buffer system containing surfactants (cetyltrimethyl ammonium bromide or sodium dodecyl sulfate or nonylphenol polyoxyethylene ether), the enantioselective reduction of 4’-chloroacetophenone to its corresponding chiral alcohol (S)-1-4’-chlorophenyl ethanol catalyzed by yeast cells were investigated. The results indicated that the conversion of 4’-chloroacetophenone was distinctly improved and the enantiomeric excess of product (S)-1-4’-chlorophenyl ethanol was barely changed when the surfactants were added to the system. Nonylphenol polyoxyethylene ether (NP-4) was the most appropriate additive among being added surfactants. In addition, the influence of nonionic surfactant NP-4 on the enantioselective reduction of aromatic ketones was studied. The results showed that the enantiomeric excesses of products (S)-1-aryl ethanol had little change and the conversions of all aromatic ketones were significantly enhanced in the presence of NP-4. It was also found that the increase of the substrate conversion was relevant to the electronic effect of the substituents on the aromatic ring. The stronger electron-donating capacity of the substituents was more beneficial to the increase of the substrate conversion.

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刘湘.表面活性剂介入酵母细胞催化芳香酮的对映选择性还原[J].精细化工,2014,31(5):

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  • 收稿日期:2014-01-07
  • 最后修改日期:2014-02-26
  • 录用日期:2014-03-10
  • 在线发布日期: 2014-05-04
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