3-[2-(1-benzyl-1H-indol-3-yl)ethylamino]propionic acid methyl ester | 874916-38-8

• 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: 3-[2-(1-benzyl-1H-indol-3-yl)ethylamino]propionic acid methyl ester
• 英文别名: Methyl 3-[2-(1-benzylindol-3-yl)ethylamino]propanoate
• CAS: 874916-38-8
• 化学式: C₂₁H₂₄N₂O₂
• 分子量: 336.434
• InChiKey: ODQGAGSSKRXFSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[2-(1-benzyl-1H-indol-3-yl)ethylamino]propionic acid methyl ester 在 potassium tert-butylate 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 50.0h， 生成 (11-benzyl-1-hydroxy-11b-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indol-1-yl)acetic acid ethyl ester
  参考文献：
  名称：

  Facile Construction of the Pentacyclic Framework of Subincanadine B. Synthesis of 20-Deethylenylated Subincanadine B and 19,20-Dihydrosubincanadine B

  摘要：

  We describe a facile approach for effectively constructing the pentacyclic framework of subincanadine B. The seven-step assembly of tetracyclic ketone 14 featured Michael addition, Pictet-Spengler cyclization, and Dieckmann condensation. From this key ketone intermediate, two analogues of subincanadine 13, i.e., 20-deethylenylated subincanadine B (27) and 19,20-dihydrosubincanadine B (31), were synthesized in four steps, respectively.

  DOI：

  10.1021/ol0526367
• 作为产物：
  描述：

  2-(2-(1H-吲哚-3-基)乙基)异吲哚啉-1,3-二酮 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[2-(1-benzyl-1H-indol-3-yl)ethylamino]propionic acid methyl ester
  参考文献：
  名称：

  Facile Construction of the Pentacyclic Framework of Subincanadine B. Synthesis of 20-Deethylenylated Subincanadine B and 19,20-Dihydrosubincanadine B

  摘要：

  We describe a facile approach for effectively constructing the pentacyclic framework of subincanadine B. The seven-step assembly of tetracyclic ketone 14 featured Michael addition, Pictet-Spengler cyclization, and Dieckmann condensation. From this key ketone intermediate, two analogues of subincanadine 13, i.e., 20-deethylenylated subincanadine B (27) and 19,20-dihydrosubincanadine B (31), were synthesized in four steps, respectively.

  DOI：

  10.1021/ol0526367

文献信息

• Facile Construction of the Pentacyclic Framework of Subincanadine B. Synthesis of 20-Deethylenylated Subincanadine B and 19,20-Dihydrosubincanadine B
  作者：Yanqin Liu、Shengjun Luo、Xingnian Fu、Fang、Zeyang Zhuang、Wanting Xiong、Xueshun Jia、Hongbin Zhai

  DOI：10.1021/ol0526367

  日期：2006.1.1

  We describe a facile approach for effectively constructing the pentacyclic framework of subincanadine B. The seven-step assembly of tetracyclic ketone 14 featured Michael addition, Pictet-Spengler cyclization, and Dieckmann condensation. From this key ketone intermediate, two analogues of subincanadine 13, i.e., 20-deethylenylated subincanadine B (27) and 19,20-dihydrosubincanadine B (31), were synthesized in four steps, respectively.