(2S,5S,11bR)-5-benzyloxycarbonyl-2-(benzyloxycarbonyl)amino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino<8,7-b>indole | 170552-56-4

• 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,5S,11bR)-5-benzyloxycarbonyl-2-(benzyloxycarbonyl)amino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino<8,7-b>indole
• 英文别名: benzyl (2S,5S,11bR)-3-oxo-2-(phenylmethoxycarbonylamino)-1,2,5,6,11,11b-hexahydroindolizino[8,7-b]indole-5-carboxylate
• CAS: 170552-56-4
• 化学式: C₃₀H₂₇N₃O₅
• 分子量: 509.561
• InChiKey: ZQDYDDRFKWDOFB-NXCFDTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5S,11bR)-5-benzyloxycarbonyl-2-(benzyloxycarbonyl)amino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino<8,7-b>indole 在 palladium on activated charcoal 二碳酸二叔丁酯 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以20%的产率得到(2S,5S,11bR)-2-Amino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carboxylic acid
  参考文献：
  名称：

  2-Amino-3-oxohexahydroindolizino[8,7-b]indole-5-carboxylate derivatives as new scaffolds for mimicking β-turn secondary structures. Molecular dynamics and stereoselective synthesis

  摘要：

  Highly constrained 2-amino-3-oxohexahydroindolizino[8-7-b]indole-5-carboxylate derivatives of general formula 1 have been developed as novel beta-turn mimetics. Molecular dynamics studies on model structures 2a and 2b have revealed that both indolizinoindole derivatives are able to adopt conformations close to those of ideal type II' beta-turn. The asymmetric synthesis of this heterocyclic system was accomplished from 1,3-di- and 1,2,3-trisubstituted tetrahydro-beta-carbolines, which were prepared in stereoselective or stereospecific way by application of the Pictet-Spengler reaction.

  DOI：

  10.1016/0040-4020(95)00402-t
• 作为产物：
  描述：

  (1S,3S,2'S)-3-benzyloxycarbonyl-1-<2'-benzyloxycarbonyl-2'-(benzyloxycarbonyl)-amino>ethyl-1,2,3,4-tetrahydro-β-carboline 在 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以63%的产率得到(2S,5S,11bR)-5-benzyloxycarbonyl-2-(benzyloxycarbonyl)amino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino<8,7-b>indole
  参考文献：
  名称：

  2-Amino-3-oxohexahydroindolizino[8,7-b]indole-5-carboxylate derivatives as new scaffolds for mimicking β-turn secondary structures. Molecular dynamics and stereoselective synthesis

  摘要：

  Highly constrained 2-amino-3-oxohexahydroindolizino[8-7-b]indole-5-carboxylate derivatives of general formula 1 have been developed as novel beta-turn mimetics. Molecular dynamics studies on model structures 2a and 2b have revealed that both indolizinoindole derivatives are able to adopt conformations close to those of ideal type II' beta-turn. The asymmetric synthesis of this heterocyclic system was accomplished from 1,3-di- and 1,2,3-trisubstituted tetrahydro-beta-carbolines, which were prepared in stereoselective or stereospecific way by application of the Pictet-Spengler reaction.

  DOI：

  10.1016/0040-4020(95)00402-t