3-amino-4-(1H-3-indolyl)butanoic acid ethyl ester | 854457-04-8

• 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: 3-amino-4-(1H-3-indolyl)butanoic acid ethyl ester
• CAS: 854457-04-8
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: PRQNJHUKVQSAOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.11
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-amino-4-(1H-3-indolyl)butanoic acid ethyl ester 、 丁酸丁酯 在 Candida antarctica lipase A*celite 作用下， 以 异丙醚 为溶剂， 反应 16.0h， 以0.62 g的产率得到ethyl (3R)-3-(butanoylamino)-4-(1H-indol-3-yl)butanoate
  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 盐酸 、 potassium carbonate 、 苯硫酚 作用下， 以 乙腈 为溶剂， 反应 48.5h， 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

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.