(1R,3S,2'S)-1-<2'-(tert-butoxycarbonyl)amino-2'-carboxy>ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline | 170300-15-9

• 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: (1R,3S,2'S)-1-<2'-(tert-butoxycarbonyl)amino-2'-carboxy>ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline
• CAS: 170300-15-9
• 化学式: C₂₁H₂₇N₃O₆
• 分子量: 417.462
• InChiKey: MHLQEJBYODJKEA-PMPSAXMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  129.75
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,3S,2'S)-1-<2'-(tert-butoxycarbonyl)amino-2'-carboxy>ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline 以 xylene 为溶剂， 以48%的产率得到(2S,5S,11bR)-2-(tert-butoxycarbonyl)amino-5-methoxycarbonyl-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：

  (1R,3S,2'S)-2-benzyl-1-<2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)amino>ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以81%的产率得到(1R,3S,2'S)-1-<2'-(tert-butoxycarbonyl)amino-2'-carboxy>ethyl-3-methoxycarbonyl-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