N-[(2R)-1-cyano-3-(1H-indol-3-yl)propan-2-yl]butanamide | 854457-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-[(2R)-1-cyano-3-(1H-indol-3-yl)propan-2-yl]butanamide
• CAS: 854457-12-8
• 化学式: C₁₆H₁₉N₃O
• 分子量: 269.346
• InChiKey: KIAWGCFHQTVESP-ZDUSSCGKSA-N

物化性质

• 沸点：
  585.1±50.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(2R)-1-cyano-3-(1H-indol-3-yl)propan-2-yl]butanamide 、 乙醇 在 盐酸 作用下， 反应 48.0h， 生成 3-amino-4-(1H-3-indolyl)butanoic acid ethyl ester
  参考文献：
  名称：

  Chemoenzymatic preparation of the enantiomers of β-tryptophan ethyl ester and the β-amino nitrile analogue

  摘要：

  Racemic alpha-tryptophan was chemoselectively transformed into the enantiomers of beta-tryptophan ethyl ester. The key step in achieving enantiopurity was the N-acylation of the 3-amino-4-(3-indolyl)butanenitrile intermediate with Candida antarctica lipase A (CAL-A). The enzymatic N-acylation of racemic beta-tryptophan ethyl ester was also studied. CAL-A was highly (R)-enantioselective in the present kinetic resolutions, leading to a mixture of the butanamide product with an (R)-configuration and the unreacted starting material with an (S)-configuration at 50% conversion. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.016
• 作为产物：
  描述：

  3-(2-nitrobenzenesulfonyl)amino-4-(1H-3-indolyl)butanenitrile 在 Candida antarctica lipase A*celite 、 potassium carbonate 、 苯硫酚 作用下， 以 异丙醚 、 乙腈 为溶剂， 反应 0.5h， 生成 N-[(2R)-1-cyano-3-(1H-indol-3-yl)propan-2-yl]butanamide
  参考文献：
  名称：

  Chemoenzymatic preparation of the enantiomers of β-tryptophan ethyl ester and the β-amino nitrile analogue

  摘要：

  Racemic alpha-tryptophan was chemoselectively transformed into the enantiomers of beta-tryptophan ethyl ester. The key step in achieving enantiopurity was the N-acylation of the 3-amino-4-(3-indolyl)butanenitrile intermediate with Candida antarctica lipase A (CAL-A). The enzymatic N-acylation of racemic beta-tryptophan ethyl ester was also studied. CAL-A was highly (R)-enantioselective in the present kinetic resolutions, leading to a mixture of the butanamide product with an (R)-configuration and the unreacted starting material with an (S)-configuration at 50% conversion. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.016

文献信息

• Chemoenzymatic preparation of the enantiomers of β-tryptophan ethyl ester and the β-amino nitrile analogue
  作者：Xiang-Guo Li、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2005.03.016

  日期：2005.5

  Racemic alpha-tryptophan was chemoselectively transformed into the enantiomers of beta-tryptophan ethyl ester. The key step in achieving enantiopurity was the N-acylation of the 3-amino-4-(3-indolyl)butanenitrile intermediate with Candida antarctica lipase A (CAL-A). The enzymatic N-acylation of racemic beta-tryptophan ethyl ester was also studied. CAL-A was highly (R)-enantioselective in the present kinetic resolutions, leading to a mixture of the butanamide product with an (R)-configuration and the unreacted starting material with an (S)-configuration at 50% conversion. (C) 2005 Elsevier Ltd. All rights reserved.