(+/-)-4-cyano-5-methyl-4-phenylhexyl acetate | 352196-06-6

• 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: (+/-)-4-cyano-5-methyl-4-phenylhexyl acetate
• 英文别名: (4-Cyano-5-methyl-4-phenylhexyl) acetate
• CAS: 352196-06-6
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: YGTJNOREUGPRMK-UHFFFAOYSA-N

物化性质

• 沸点：
  400.0±35.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-4-cyano-5-methyl-4-phenylhexyl acetate 在 甲基叔丁基醚 、 immobilized Pseudomonas sp. lipase 、 水 作用下， 反应 24.0h， 生成 (2S)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile 、 (R)-(-)-4-cyano-5-methyl-4-phenylhexanol 、 (S)-(-)-4-cyano-5-methyl-4-phenylhexyl acetate 、 (R)-(+)-4-cyano-5-methyl-4-phenylhexyl acetate
  参考文献：
  名称：

  Enantioselective synthesis of (2S)-5-{4-[2-(4-fluorophenoxy)ethyl]piperazin-1-yl}-2-isopropyl-2-phenyl-pentanenitrile dihydrochloride (E2050) using enzyme-catalyzed kinetic resolution

  摘要：

  Immobilized lipase (Pseudomonas sp.)-catalyzed transesterification of (RS)-4-cyano-4-isopropyl-4-phenyl-1-butanol 4 in vinyl acetate gave (S)-4-cyano-4-isopropyl-4-phenyl-1-butyl acetate 3a with high enantiomeric excess values and conversions (95-97% ee, 30-47%, E = 90-93), leaving the enantiomerically pure (R)-alcohol 4 (>99% ee) unreacted. As 3a can be efficiently converted to E2050, use of the immobilized lipase should provide an economical route for large-scale synthesis of E2050. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00364-6
• 作为产物：
  描述：

  2-异丙基-2-苯基乙腈 在 吡啶 、 lithium aluminium tetrahydride 、 18-冠醚-6 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 (+/-)-4-cyano-5-methyl-4-phenylhexyl acetate
  参考文献：
  名称：

  Enantioselective synthesis of (2S)-5-{4-[2-(4-fluorophenoxy)ethyl]piperazin-1-yl}-2-isopropyl-2-phenyl-pentanenitrile dihydrochloride (E2050) using enzyme-catalyzed kinetic resolution

  摘要：

  Immobilized lipase (Pseudomonas sp.)-catalyzed transesterification of (RS)-4-cyano-4-isopropyl-4-phenyl-1-butanol 4 in vinyl acetate gave (S)-4-cyano-4-isopropyl-4-phenyl-1-butyl acetate 3a with high enantiomeric excess values and conversions (95-97% ee, 30-47%, E = 90-93), leaving the enantiomerically pure (R)-alcohol 4 (>99% ee) unreacted. As 3a can be efficiently converted to E2050, use of the immobilized lipase should provide an economical route for large-scale synthesis of E2050. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00364-6