4-hydroxy-3-[1H-indol-3-yl-(4-nitrophenyl)methyl]-6-methylpyran-2-one | 1191399-86-6

• 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: 4-hydroxy-3-[1H-indol-3-yl-(4-nitrophenyl)methyl]-6-methylpyran-2-one
• CAS: 1191399-86-6
• 化学式: C₂₁H₁₆N₂O₅
• 分子量: 376.368
• InChiKey: WCDZCROPSJKFQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吲哚 、 4-羟基-6-甲基-2-吡喃酮 、 对硝基苯甲醛 以 氯仿 、 水 为溶剂， 反应 72.0h， 以59%的产率得到4-hydroxy-3-[1H-indol-3-yl-(4-nitrophenyl)methyl]-6-methylpyran-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

文献信息

• A multicomponent synthesis of gem-(β-dicarbonyl)arylmethanes
  作者：Giovanni Appendino、Lavinia Cicione、Alberto Minassi

  DOI：10.1016/j.tetlet.2009.05.033

  日期：2009.10

  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.