(S)-(+)-1-cyano-1-cyclohexyl-1-phenylmethyl hydroxyacetate

• 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)-(+)-1-cyano-1-cyclohexyl-1-phenylmethyl hydroxyacetate
• 英文别名: [(S)-cyano-cyclohexyl-phenylmethyl] 2-hydroxyacetate
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: WYDZVXFSFLULME-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-[(1-cyano-1-cyclohexyl-1-phenylmethoxy)carbonyl]methyl acetate 在 Novozym 435 、 immobilized Pseudomonas cepacia lipase 作用下， 以 1,4-二氧六环 、 phosphate buffer 、 甲苯 为溶剂， 反应 88.0h， 生成 (S)-(+)-1-cyano-1-cyclohexyl-1-phenylmethyl hydroxyacetate
  参考文献：
  名称：

  Enzymatic resolution of hindered cyanohydrins, key precursors of muscarinic receptor antagonists

  摘要：

  Enantiomerically pure 1-cycloalkyl-1-hydroxy-1-phenylcyanohydrins, key precursors in the synthesis of (S)-oxybutynin and other antimuscarinic agents, have been successfully prepared via lipase-catalyzed kinetic resolutions. Pseudomonas cepacia and Candida antarctica lipase B have shown excellent enantioselectivities in hydrolysis and acylation processes, depending on the substrate structure and the reaction conditions. Furthermore, molecular modeling of phosphonate transition state analogue for the C antarctica lipase B enzymatic hydrolysis resolution step supports these facts, which were experimentally observed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.002

文献信息

• Enzymatic resolution of hindered cyanohydrins, key precursors of muscarinic receptor antagonists
  作者：Verónica Recuero、Miguel Ferrero、Vicente Gotor-Fernández、Rosario Brieva、Vicente Gotor

  DOI：10.1016/j.tetasy.2007.04.002

  日期：2007.5

  Enantiomerically pure 1-cycloalkyl-1-hydroxy-1-phenylcyanohydrins, key precursors in the synthesis of (S)-oxybutynin and other antimuscarinic agents, have been successfully prepared via lipase-catalyzed kinetic resolutions. Pseudomonas cepacia and Candida antarctica lipase B have shown excellent enantioselectivities in hydrolysis and acylation processes, depending on the substrate structure and the reaction conditions. Furthermore, molecular modeling of phosphonate transition state analogue for the C antarctica lipase B enzymatic hydrolysis resolution step supports these facts, which were experimentally observed. (c) 2007 Elsevier Ltd. All rights reserved.