4-hydroxy-3-[1-(1H-indol-3-yl)ethyl]chromen-2-one | 1191399-78-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-hydroxy-3-[1-(1H-indol-3-yl)ethyl]chromen-2-one
• CAS: 1191399-78-6
• 化学式: C₁₉H₁₅NO₃
• 分子量: 305.333
• InChiKey: ITZVBIUPIKWEBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 4-羟基香豆素 、 乙醛 以 氯仿 为溶剂， 反应 5.0h， 以88%的产率得到4-hydroxy-3-[1-(1H-indol-3-yl)ethyl]chromen-2-one
  参考文献：
  名称：

  A multicomponent synthesis of gem-(β-dicarbonyl)arylmethanes

  摘要：

  The reaction of aldehydes with beta-dicarbonyls and electron-rich aromatics was investigated to generate in a multicomponent fashion crossed adducts of biological relevance. 4-Hydroxycoumarin, triacetic acid lactone, indole, and a selection of aliphatic and aromatic aldehydes representative of various electronic and steric conditions were employed. The reaction showed a surprising dependence on the solvent, with 1:1 chloroform-water giving the best yield of heterodimeric adducts. The mechanistic rationale for the formation of hetero- rather than homodimeric adducts is discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.033