trans-ethyl-2-(2-bromoethyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate | 1447959-81-0

• 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: trans-ethyl-2-(2-bromoethyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate
• 英文别名: ethyl (1R,3S)-2-(2-bromoethyl)-1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
• CAS: 1447959-81-0
• 化学式: C₂₂H₂₃BrN₂O₂
• 分子量: 427.341
• InChiKey: MWKUENICRTZYCX-PZJWPPBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-ethyl-2-(2-bromoethyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate 、 对氯苄胺 以 乙醇 为溶剂， 反应 24.0h， 以92%的产率得到trans-2-(4-chlorobenzyl)-6-phenyl-3,4,6,7,12,12a-hexahydro-2H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-1-one
  参考文献：
  名称：

  Synthesis of Functionalized Diketopiperazines as Cyclotryprostatin and Tryprostatin Analogues

  摘要：

  Various ketopiperazines were synthesized as (cyclo) tryprostatin analogues. Construction of the skeleton started with a Pictet-Spengler reaction followed by acylation or alkylation of the piperidine nitrogen and condensation with a primary amine. 2-Chloroacetyl tetrahydro-beta-carbolines rearranged towards the corresponding 2-chloro-N-[2-(1H-indol-3-yl)ethyl]acetamide derivatives upon treatment with NBS. These compounds were cyclized with primary amines towards the corresponding functionalized diketopiperazines.

  DOI：

  10.1055/s-0032-1316911
• 作为产物：
  描述：

  D-色氨酸乙酯盐酸盐 在 potassium carbonate 作用下， 以 苯 为溶剂， 反应 72.0h， 生成 trans-ethyl-2-(2-bromoethyl)-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate
  参考文献：
  名称：

  Synthesis of Functionalized Diketopiperazines as Cyclotryprostatin and Tryprostatin Analogues

  摘要：

  Various ketopiperazines were synthesized as (cyclo) tryprostatin analogues. Construction of the skeleton started with a Pictet-Spengler reaction followed by acylation or alkylation of the piperidine nitrogen and condensation with a primary amine. 2-Chloroacetyl tetrahydro-beta-carbolines rearranged towards the corresponding 2-chloro-N-[2-(1H-indol-3-yl)ethyl]acetamide derivatives upon treatment with NBS. These compounds were cyclized with primary amines towards the corresponding functionalized diketopiperazines.

  DOI：

  10.1055/s-0032-1316911