(S)-9-Methyl-6-oxo-1,2,6,7-tetrahydro-10-oxa-8,10b-diaza-benzo[cd]cyclopenta[h]azulene-1-carboxylic acid methyl ester | 160726-14-7

• 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)-9-Methyl-6-oxo-1,2,6,7-tetrahydro-10-oxa-8,10b-diaza-benzo[cd]cyclopenta[h]azulene-1-carboxylic acid methyl ester
• 英文别名: methyl (15S)-4-methyl-8-oxo-3-oxa-1,5-diazatetracyclo[7.6.1.02,6.013,16]hexadeca-2(6),4,9,11,13(16)-pentaene-15-carboxylate
• CAS: 160726-14-7
• 化学式: C₁₆H₁₄N₂O₄
• 分子量: 298.298
• InChiKey: DXOSSJTZGGVPFO-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-9-Methyl-6-oxo-1,2,6,7-tetrahydro-10-oxa-8,10b-diaza-benzo[cd]cyclopenta[h]azulene-1-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 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 palladium on activated charcoal 三氯化铝 、 草酰氯 、 氢气 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 (S)-9-Methyl-6-oxo-1,2,6,7-tetrahydro-10-oxa-8,10b-diaza-benzo[cd]cyclopenta[h]azulene-1-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

文献信息

• Practical syntheses of a novel tricyclic dipeptide mimetic based on a [6H]-azepino indoline nucleus: Application to angiotensin-converting enzyme inhibition
  作者：Stéphane De Lombaert、Louis Blanchard、Lisa B. Stamford、Donald M. Sperbeck、Michael D. Grim、Todd M. Jenson、Herman R. Rodriguez

  DOI：10.1016/s0040-4039(00)78331-6

  日期：1994.10

  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).