(2S,5R)-4-Oxo-5-(2,2,2-trifluoro-acetylamino)-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indole-2-carboxylic acid methyl ester | 160726-08-9

• 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: (2S,5R)-4-Oxo-5-(2,2,2-trifluoro-acetylamino)-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indole-2-carboxylic acid methyl ester
• CAS: 160726-08-9
• 化学式: C₁₆H₁₅F₃N₂O₄
• 分子量: 356.301
• InChiKey: AISPAAZDYKETNJ-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,5R)-4-Oxo-5-(2,2,2-trifluoro-acetylamino)-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indole-2-carboxylic acid methyl ester 在 盐酸 、 lithium hydroxide 作用下， 以94%的产率得到(2S,5R)-5-Amino-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indole-2-carboxylic acid methyl ester; hydrochloride
  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)-(-)-2-(三氟乙酰胺)琥珀酸酐 在 palladium on activated charcoal 三氯化铝 、 草酰氯 、 氢气 、 N,N-二甲基甲酰胺 作用下， 以 溶剂黄146 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 25.0h， 生成 (2S,5R)-4-Oxo-5-(2,2,2-trifluoro-acetylamino)-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