(S)-3-acetoxy-3-phenylpropanenitrile | 21087-76-3

• 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)-3-acetoxy-3-phenylpropanenitrile
• 英文别名: (S)-2-cyano-1-phenylethyl acetate；[(1S)-2-cyano-1-phenylethyl] acetate
• CAS: 21087-76-3
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: IOINVUDAFYPKGX-NSHDSACASA-N

物化性质

• 沸点：
  327.9±30.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+/-)-3-acetyloxy-3-phenylpropanenitrile 在 phosphate buffer 、 Pseudomonas cepacia lipase on modified ceramic particles 作用下， 反应 14.0h， 以41%的产率得到(R)-3-phenyl-3-hydroxypropanenitrile
  参考文献：
  名称：

  A new facile chemoenzymatic synthesis of levamisole

  摘要：

  An efficient and facile chemoenzymatic synthesis of levamisole by employing lipase-mediated resolution of 3-hydroxy-3-phenylpropanenitrile followed by its conversion to beta-amino alcohol as the key intermediate is described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.054

文献信息

• Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. A Route to Useful Precursors for γ-Amino Alcohols
  作者：Oscar Pàmies、Jan-E. Bäckvall

  DOI：10.1002/1615-4169(200108)343:6/7<726::aid-adsc726>3.3.co;2-5

  日期：2001.8
• Study of the enantioselectivity of the CAL-B-catalysed transesterification of α-substituted α-propylmethanols and α-substituted benzyl alcohols
  作者：Eduardo Garcı́a-Urdiales、Francisca Rebolledo、Vicente Gotor

  DOI：10.1016/s0957-4166(01)00532-8

  日期：2001.11

  A study of the enantioselectivity exhibited by the lipase B from Candida antarctica in the transesterification of different alpha-substituted alpha-propylmethanols with vinyl acetate is shown. The best results are obtained when the large-sized (L) substituent of the alcohol is either a phenyl group or more especially a cyclohexyl group, although the reaction rates are lower than when linear or slightly branched groups are present. It is also found that ramification at the beta-position of the L substituent has a deleterious effect on both lipase activity and enantioselectivity. Moreover, some alpha-substituted benzyl alcohols bearing medium-sized (M) substituents larger than an ethyl and smaller than a propyl group are resolved by means of this methodology with moderate-good enantioselectivities (E=46-57) and similar reaction rates. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A new facile chemoenzymatic synthesis of levamisole
  作者：Ahmed Kamal、G.B. Ramesh Khanna、T. Krishnaji、R. Ramu

  DOI：10.1016/j.bmcl.2004.11.054

  日期：2005.2

  An efficient and facile chemoenzymatic synthesis of levamisole by employing lipase-mediated resolution of 3-hydroxy-3-phenylpropanenitrile followed by its conversion to beta-amino alcohol as the key intermediate is described. (C) 2004 Elsevier Ltd. All rights reserved.