1-Methyl-3-(2-methyl-4-phenyloxolan-2-yl)indole | 1198229-49-0

• 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: 1-Methyl-3-(2-methyl-4-phenyloxolan-2-yl)indole
• CAS: 1198229-49-0
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: IBAXNGKLEUATIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-甲基吲哚 、 2-phenyl-4-pentyn-1-ol 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以62%的产率得到1-Methyl-3-(2-methyl-4-phenyloxolan-2-yl)indole
  参考文献：
  名称：

  Thorpe–Ingold effect in copper(II)-catalyzed formal hydroalkoxylation–hydroarylation reaction of alkynols with indoles

  摘要：

  The use of Cu(OTf)(2) as a catalyst for tandem hydroalkoxylation-hydroarylation reaction of alkynes tethered with hydroxyl group is reported. The reaction proceeds at 60 degrees C or even at room temperature with 5 mol% catalyst loading and produces C-3-substituted indoles in good to high yields. The method was shown to be applicable to a broad range of indoles, containing electron-withdrawing and electron-donating substituents, and alkynol substrates bearing sterically demanding substituents in the tether. Interestingly, it was found that Thorpe-Ingold effect is operating for this cyclization reaction. Easy availability and low cost of Cu(OTf)(2) make this method attractive and amenable for large-scale synthesis compared to known literature methods. (C) 2009 Published by Elsevier Ltd

  DOI：

  10.1016/j.tetlet.2009.09.057