1-Methyl-3-(2-methyl-4,4-diphenyloxolan-2-yl)-4-nitroindole | 1198229-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Methyl-3-(2-methyl-4,4-diphenyloxolan-2-yl)-4-nitroindole
• CAS: 1198229-56-9
• 化学式: C₂₆H₂₄N₂O₃
• 分子量: 412.488
• InChiKey: UPRXUGFNJTZVLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2-diphenylpent-4-yn-1-ol 、 1-甲基-4-硝基-1H-吲哚 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以78%的产率得到1-Methyl-3-(2-methyl-4,4-diphenyloxolan-2-yl)-4-nitroindole
  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

文献信息

• Thorpe–Ingold effect in copper(II)-catalyzed formal hydroalkoxylation–hydroarylation reaction of alkynols with indoles
  作者：Nitin T. Patil、Vivek S. Raut、Rahul D. Kavthe、Vaddu V.N. Reddy、P.V.K. Raju

  DOI：10.1016/j.tetlet.2009.09.057

  日期：2009.11

  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