(S)-4-(2-aminophenyl)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid | 1409999-05-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-(2-aminophenyl)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid
• 英文别名: (2S)-4-(2-aminophenyl)-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 1409999-05-8
• 化学式: C₁₈H₁₈N₂O₅
• 分子量: 342.351
• InChiKey: GXVNQZYPZGWSGR-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-(2-aminophenyl)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 硫酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以65%的产率得到L-犬尿氨酸硫酸盐
  参考文献：
  名称：

  A concise preparation of the non-proteinogenic amino acid l-kynurenine

  摘要：

  A concise and practical preparation of the non-proteinogenic amino acid L-kynurenine is reported. The synthetic approach is scalable and provides ready access to this valuable amino acid in either L- or D-stereochemistry starting from L- or D-tryptophan, respectively. In the optimized procedure, two discreet oxidation steps are applied sequentially to convert the tryptophan indole ring into the keto-aniline moiety contained within the kynurenine side chain. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.055
• 作为产物：
  描述：

  (S)-2-(((benzyloxy)carbonyl)amino)-3-(2-oxoindolin-3-yl)propanoic acid 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以52%的产率得到(S)-4-(2-aminophenyl)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid
  参考文献：
  名称：

  A concise preparation of the non-proteinogenic amino acid l-kynurenine

  摘要：

  A concise and practical preparation of the non-proteinogenic amino acid L-kynurenine is reported. The synthetic approach is scalable and provides ready access to this valuable amino acid in either L- or D-stereochemistry starting from L- or D-tryptophan, respectively. In the optimized procedure, two discreet oxidation steps are applied sequentially to convert the tryptophan indole ring into the keto-aniline moiety contained within the kynurenine side chain. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.055

文献信息

• A concise preparation of the non-proteinogenic amino acid l-kynurenine
  作者：Laurens H.J. Kleijn、Frederike M. Müskens、Sabine F. Oppedijk、Gerjan de Bruin、Nathaniel I. Martin

  DOI：10.1016/j.tetlet.2012.09.055

  日期：2012.11

  A concise and practical preparation of the non-proteinogenic amino acid L-kynurenine is reported. The synthetic approach is scalable and provides ready access to this valuable amino acid in either L- or D-stereochemistry starting from L- or D-tryptophan, respectively. In the optimized procedure, two discreet oxidation steps are applied sequentially to convert the tryptophan indole ring into the keto-aniline moiety contained within the kynurenine side chain. (C) 2012 Elsevier Ltd. All rights reserved.