(+/-)-[(1-cyano-1-cyclohexyl-1-phenylmethoxy)carbonyl]methyl acetate | 944324-90-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-[(1-cyano-1-cyclohexyl-1-phenylmethoxy)carbonyl]methyl acetate
• CAS: 944324-90-7
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: FZBOLGZOCYLNHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.39
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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 (R)-(-)-[(1-cyano-1-cyclohexyl-1-phenylmethoxy)carbonyl]methyl benzoate
  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
• 作为产物：
  描述：

  环己基苯基甲酮 在 吡啶 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (+/-)-[(1-cyano-1-cyclohexyl-1-phenylmethoxy)carbonyl]methyl acetate
  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