(S)-1-((S)-2-Acetylamino-3-benzyloxycarbonyl-propionyl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester | 160726-11-4

• 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: (S)-1-((S)-2-Acetylamino-3-benzyloxycarbonyl-propionyl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester
• CAS: 160726-11-4
• 化学式: C₂₃H₂₄N₂O₆
• 分子量: 424.453
• InChiKey: XGFWNPRMPCBEBG-ICSRJNTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-1-((S)-2-Acetylamino-3-benzyloxycarbonyl-propionyl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以78%的产率得到(S)-1-(4-Benzyloxycarbonylmethyl-2-methyl-oxazol-5-yl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Practical syntheses of a novel tricyclic dipeptide mimetic based on a [6H]-azepino indoline nucleus: Application to angiotensin-converting enzyme inhibition

  摘要：

  Two stereocontrolled synthetic approaches towards 5-(S)-amino-1,2,4,5,6,7-hexahydro-azepino [3,2,1-hi] indole-4-one-2-(S)-carboxylic acid 1, based on intramolecular Friedel-Crafts acylations, are reported. This conformationally restricted tricyclic dipeptidomimetic has been applied a the design of a potent and orally active inhibitor of angiotensin-converting enzyme (ACE).

  DOI：

  10.1016/s0040-4039(00)78331-6
• 作为产物：
  描述：

  methyl (2S)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-phenylmethoxybutanoyl]-2,3-dihydroindole-2-carboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 (S)-1-((S)-2-Acetylamino-3-benzyloxycarbonyl-propionyl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Practical syntheses of a novel tricyclic dipeptide mimetic based on a [6H]-azepino indoline nucleus: Application to angiotensin-converting enzyme inhibition

  摘要：

  Two stereocontrolled synthetic approaches towards 5-(S)-amino-1,2,4,5,6,7-hexahydro-azepino [3,2,1-hi] indole-4-one-2-(S)-carboxylic acid 1, based on intramolecular Friedel-Crafts acylations, are reported. This conformationally restricted tricyclic dipeptidomimetic has been applied a the design of a potent and orally active inhibitor of angiotensin-converting enzyme (ACE).

  DOI：

  10.1016/s0040-4039(00)78331-6