cis-ethyl 2-(2-chloroacetyl)-1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate | 1447959-78-5

• 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: cis-ethyl 2-(2-chloroacetyl)-1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate
• CAS: 1447959-78-5
• 化学式: C₂₃H₂₃ClN₂O₄
• 分子量: 426.9
• InChiKey: NKNCZOGRIMDABZ-UGKGYDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  cis-ethyl 2-(2-chloroacetyl)-1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 1-butyl-3-((2-(4-methoxybenzoyl)-1H-indol-3-yl)methyl)piperazine-2,5-dione
  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 碳酸氢钠 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 48.5h， 生成 cis-ethyl 2-(2-chloroacetyl)-1-(4-methoxyphenyl)-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