(S)-1-(4-Benzyloxycarbonylmethyl-2-methyl-oxazol-5-yl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester | 160726-12-5

• 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-(4-Benzyloxycarbonylmethyl-2-methyl-oxazol-5-yl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester
• CAS: 160726-12-5
• 化学式: C₂₃H₂₂N₂O₅
• 分子量: 406.438
• InChiKey: MJKWJTLVSNAERN-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  81.87
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-Benzyloxycarbonylmethyl-2-methyl-oxazol-5-yl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester 在 palladium on activated charcoal 三氯化铝 、 草酰氯 、 氢气 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 (2S,5S)-5-Acetylamino-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]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：

  (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