2-[2-(1H-indol-3-yl)ethyl]isoindolin-1-one | 67388-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[2-(1H-indol-3-yl)ethyl]isoindolin-1-one
• 英文别名: N-<β-(3-Indolylethyl)>phthalimidin；2-(2-indol-3-yl-ethyl)-2,3-dihydro-isoindol-1-one；2-[2-(1H-indol-3-yl)ethyl]-3H-isoindol-1-one
• CAS: 67388-58-3
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: DDMVECZGHDTXRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  色胺 、 邻苯二甲醛 在 硼酸 、 溶剂黄146 作用下， 反应 1.0h， 生成 2-[2-(1H-indol-3-yl)ethyl]isoindolin-1-one
  参考文献：
  名称：

  Comparative evaluation of a Pictet–Spengler protocol in microwave-assisted conversions of tryptamine with aryl- and carboxyaryl aldehydes: role of ring strain in cyclocondensation of the primarily formed carboxyaryl-substituted β-carbolines

  摘要：

  An efficient microwave-assisted Pictet-Spengler protocol employing boric acid/acetic acid as a catalytic system was elaborated for the synthesis of 1-aryl-beta-carbolines. Under the novel conditions tryptamine and 2-formylbenzoic acid furnished a pentacyclic skeleton in a single step, whereas using o-phthalaldehyde as a coupling partner led to the formation of an isoindolone derivative. Three beta-carbolines primarily resulted from the reactions involving carboxy-substituted heteroaryl aldehydes and avoided cyclisation to polycondensed skeletons with enhanced ring strain, as was evidenced by density functional theory (DFT) modelling.

  DOI：

  10.1007/s00706-013-1007-6