ethyl 3-(2-benzoyl-1H-indol-3-yl)-2-(2-chloroacetylamino)propionate | 1447960-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 3-(2-benzoyl-1H-indol-3-yl)-2-(2-chloroacetylamino)propionate
• 英文别名: ethyl 3-(2-benzoyl-1H-indol-3-yl)-2-[(2-chloroacetyl)amino]propanoate
• CAS: 1447960-06-6
• 化学式: C₂₂H₂₁ClN₂O₄
• 分子量: 412.873
• InChiKey: KZHPEUSKHYMNFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  88.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  正丙胺 、 ethyl 3-(2-benzoyl-1H-indol-3-yl)-2-(2-chloroacetylamino)propionate 以 乙醇 为溶剂， 反应 24.0h， 以80%的产率得到3-(2-benzoyl-1H-indol-3-ylmethyl)-1-propylpiperazine-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 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 苯 为溶剂， 反应 48.5h， 生成 ethyl 3-(2-benzoyl-1H-indol-3-yl)-2-(2-chloroacetylamino)propionate
  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

文献信息

• Synthesis of Functionalized Diketopiperazines as Cyclotryprostatin and Tryprostatin Analogues
  作者：Norbert De Kimpe、Tuyen Nguyen Van、Pieter Claes

  DOI：10.1055/s-0032-1316911

  日期：——

  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.