(1S,3S,2'S)-3-benzyloxycarbonyl-1-<2'-benzyloxycarbonyl-2'-(benzyloxycarbonyl)-amino>ethyl-1,2,3,4-tetrahydro-β-carboline | 170300-12-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (1S,3S,2'S)-3-benzyloxycarbonyl-1-<2'-benzyloxycarbonyl-2'-(benzyloxycarbonyl)-amino>ethyl-1,2,3,4-tetrahydro-β-carboline
• CAS: 170300-12-6
• 化学式: C₃₇H₃₅N₃O₆
• 分子量: 617.701
• InChiKey: POLCJYURPWZAHY-ZDCRTTOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  118.75
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,3S,2'S)-3-benzyloxycarbonyl-1-<2'-benzyloxycarbonyl-2'-(benzyloxycarbonyl)-amino>ethyl-1,2,3,4-tetrahydro-β-carboline 以 xylene 为溶剂， 以95%的产率得到(2S,5S,11bS)-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
• 作为产物：
  描述：

  2S-苄氧羰酰氨基-4-氧代-丁酸苄酯 、 L-色氨酸苯甲酯 在 三乙胺 、 三氟乙酸 作用下， 生成 (1S,3S,2'S)-3-benzyloxycarbonyl-1-<2'-benzyloxycarbonyl-2'-(benzyloxycarbonyl)-amino>ethyl-1,2,3,4-tetrahydro-β-carboline 、 (1R,3S,2'S)-3-benzyloxycarbonyl-1-<2'-benzyloxycarbonyl-2'-(benzyloxycarbonyl)-amino>ethyl-1,2,3,4-tetrahydro-β-carboline
  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