methyl (2S)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-phenylmethoxybutanoyl]-2,3-dihydroindole-2-carboxylate | 160726-10-3

• 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: methyl (2S)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-phenylmethoxybutanoyl]-2,3-dihydroindole-2-carboxylate
• CAS: 160726-10-3
• 化学式: C₂₆H₃₀N₂O₇
• 分子量: 482.533
• InChiKey: SAXXOFFADKMFDA-FPOVZHCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-phenylmethoxybutanoyl]-2,3-dihydroindole-2-carboxylate 在 盐酸 、 三氯氧磷 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 2.0h， 生成 (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：

  Boc-L-天冬氨酸 4-苄酯 、 (S)-(+)-吲哚啉-2-羧酸甲酯 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以79%的产率得到methyl (2S)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-phenylmethoxybutanoyl]-2,3-dihydroindole-2-carboxylate
  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

• US5644055A
  申请人：——

  公开号：US5644055A

  公开（公告）日：1997-07-01
• 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).