(S)-(+)-cyano(3-phenoxyphenyl)methyl butyrate | 298702-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(+)-cyano(3-phenoxyphenyl)methyl butyrate
• 英文别名: [(S)-cyano-(3-phenoxyphenyl)methyl] butanoate
• CAS: 298702-31-5
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: JZTLZAUEQAEOAC-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-cyano(3-phenoxyphenyl)methyl butyrate 在 吡啶 、 Pseudomonas cepacia lipase gelozyme 、 溶剂黄146 、 正丁醇 作用下， 以 正己烷 、 acetate buffer 为溶剂， 反应 3.0h， 生成 来福灵
  参考文献：
  名称：

  ‘Gelozymes’ in organic synthesis. Part 2: Candida rugosa lipase mediated synthesis of enantiomerically pure (S)-cyano(3-phenoxyphenyl)methyl butyrate

  摘要：

  Significant changes in enantioselectivity (E) have been observed when the butanoate ester of ()-1-hydroxy-1-(3-phenoxyphenyl)acetonitrile was subjected to hydrolysis in acetate buffer (pH 4.5 E=6.4) and alcoholysis with 1-butanol in hexane catalysed by Candida rugosa lipase (E=45). Enantiomerically pure (S)-butanoate ester so obtained (e.e. 98.4%) was converted to the corresponding (S)-cyanohydrin using Pseudomonas cepacia (Amano Ps) gelozyme. This strategy overcomes the problem of separation of the unwanted (R)-ester from the (S)-cyanohydrin. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00277-4
• 作为产物：
  描述：

  (R,S)-cyano(3-phenoxyphenyl)methyl butyrate 在 磷脂酶B 、 正丁醇 作用下， 以 正己烷 为溶剂， 反应 8.0h， 以70%的产率得到(S)-(+)-cyano(3-phenoxyphenyl)methyl butyrate
  参考文献：
  名称：

  ‘Gelozymes’ in organic synthesis. Part 2: Candida rugosa lipase mediated synthesis of enantiomerically pure (S)-cyano(3-phenoxyphenyl)methyl butyrate

  摘要：

  Significant changes in enantioselectivity (E) have been observed when the butanoate ester of ()-1-hydroxy-1-(3-phenoxyphenyl)acetonitrile was subjected to hydrolysis in acetate buffer (pH 4.5 E=6.4) and alcoholysis with 1-butanol in hexane catalysed by Candida rugosa lipase (E=45). Enantiomerically pure (S)-butanoate ester so obtained (e.e. 98.4%) was converted to the corresponding (S)-cyanohydrin using Pseudomonas cepacia (Amano Ps) gelozyme. This strategy overcomes the problem of separation of the unwanted (R)-ester from the (S)-cyanohydrin. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00277-4

文献信息

• Enantioselective Synthesis of Protected Cyanohydrins
  作者：Lars Veum、Marina Kuster、Selvedin Telalovic、Ulf Hanefeld、Thomas Maschmeyer

  DOI：10.1002/1099-0690(200205)2002:9<1516::aid-ejoc1516>3.0.co;2-c

  日期：2002.5

  straightforward process for the preparation of optically active protected cyanohydrins, important building blocks for the synthesis of drugs and agrochemicals, has been established. Lipase B from Candida Antarctica (CAL-B) catalysed the kinetic resolution of racemic cyanohydrin acetates under mild conditions. The resulting labile cyanohydrins were reprotected either by an enzyme-catalysed route involving the

  已经建立了制备光学活性受保护的氰醇的简单方法，该氰醇是合成药物和农用化学品的重要组成部分。来自南极念珠菌 (CAL-B) 的脂肪酶 B 在温和条件下催化外消旋醋酸氰的动力学拆分。所得不稳定的氰醇通过酶催化途径（包括加入丁酸乙烯酯）或在从反应混合物中除去酶后以化学方式再保护。该过程使两种对映异构体均以纯形式和良好的产率获得，同时显着降低了 HCN 引起的风险。还引入了各种不同的保护基团。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• ‘Gelozymes’ in organic synthesis. Part 2: Candida rugosa lipase mediated synthesis of enantiomerically pure (S)-cyano(3-phenoxyphenyl)methyl butyrate
  作者：Nitin W. Fadnavis、Ravi Luke Babu、Gurrala Sheelu、Ashlesha Deshpande

  DOI：10.1016/s0957-4166(01)00277-4

  日期：2001.7

  Significant changes in enantioselectivity (E) have been observed when the butanoate ester of ()-1-hydroxy-1-(3-phenoxyphenyl)acetonitrile was subjected to hydrolysis in acetate buffer (pH 4.5 E=6.4) and alcoholysis with 1-butanol in hexane catalysed by Candida rugosa lipase (E=45). Enantiomerically pure (S)-butanoate ester so obtained (e.e. 98.4%) was converted to the corresponding (S)-cyanohydrin using Pseudomonas cepacia (Amano Ps) gelozyme. This strategy overcomes the problem of separation of the unwanted (R)-ester from the (S)-cyanohydrin. (C) 2001 Elsevier Science Ltd. All rights reserved.