(3S,1'R)-ethyl-3-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-2-oxo-2,3,4,5-tetrahydro-1H-pyrrolo<1,2-b><1,2>diazepine-1-acetate | 140677-51-6

• 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: (3S,1'R)-ethyl-3-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-2-oxo-2,3,4,5-tetrahydro-1H-pyrrolo<1,2-b><1,2>diazepine-1-acetate
• 英文别名: (3S,1'R)-ethyl-3-{[1-(ethoxycarbonyl)-3-phenylpropyl]amino}-2-oxo-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-b][1,2]diazepine-1-acetate；ethyl (2R)-2-[[(3S)-1-(2-ethoxy-2-oxoethyl)-2-oxo-4,5-dihydro-3H-pyrrolo[1,2-b]diazepin-3-yl]amino]-4-phenylbutanoate
• CAS: 140677-51-6
• 化学式: C₂₄H₃₁N₃O₅
• 分子量: 441.527
• InChiKey: LQUIEUSAZYXLMY-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  89.87
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3S,1'R)-ethyl-3-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-2-oxo-2,3,4,5-tetrahydro-1H-pyrrolo<1,2-b><1,2>diazepine-1-acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以32%的产率得到(3S,1'R)-3-((1-carboxy-3-phenylpropyl)amino)-2-oxo-2,3,4,5-tetrahydro-1H-pyrrolo<1,2-b><1,2>diazepine-1-acetic acid
  参考文献：
  名称：

  Asymmetric synthesis of pyrrolo[1,2-b][1,2]diazepine derivatives as potential antihypertensive drugs

  摘要：

  The asymmetric synthesis of compound 1, with Potential angiotensin-converting enzyme inhibitory activity, is reported. From the chiral precursor 5, readily available from L-glutamic acid, two strategies to the key heterocyclic system pyrrolo[1,2-b][1,2]diazepine have been developed. The first one is based on the formation of the pyrrole nucleus in the early stages of the synthesis. The second strategy is based on the formation of the pyrrole in the final stages and can be regarded as a two-step Paal-Knorr N-aminopyrrole synthesis, in which intermediate N-protection is unnecessary.

  DOI：

  10.1021/jo00039a007
• 作为产物：
  描述：

  (S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 sodium ethanolate 、 一水合肼 、 magnesium 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， -65.0~50.0 ℃ 、101.33 kPa 条件下， 反应 7.25h， 生成 (3S,1'R)-ethyl-3-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-2-oxo-2,3,4,5-tetrahydro-1H-pyrrolo<1,2-b><1,2>diazepine-1-acetate
  参考文献：
  名称：

  Asymmetric synthesis of pyrrolo[1,2-b][1,2]diazepine derivatives as potential antihypertensive drugs

  摘要：

  The asymmetric synthesis of compound 1, with Potential angiotensin-converting enzyme inhibitory activity, is reported. From the chiral precursor 5, readily available from L-glutamic acid, two strategies to the key heterocyclic system pyrrolo[1,2-b][1,2]diazepine have been developed. The first one is based on the formation of the pyrrole nucleus in the early stages of the synthesis. The second strategy is based on the formation of the pyrrole in the final stages and can be regarded as a two-step Paal-Knorr N-aminopyrrole synthesis, in which intermediate N-protection is unnecessary.

  DOI：

  10.1021/jo00039a007