4-methyl-1-(triisopropylsilyl)-1H-indole

• 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-methyl-1-(triisopropylsilyl)-1H-indole
• 英文别名: (4-Methylindol-1-yl)-tri(propan-2-yl)silane
• 化学式: C₁₈H₂₉NSi
• 分子量: 287.52
• InChiKey: IYPAQDCZXWNCJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  五氟苯 、 4-methyl-1-(triisopropylsilyl)-1H-indole 在 三苯基膦氯金 、 1-pivaloyloxy-1,2-benziodoxol-3(1H)-one 、 特戊酸银 、 二甲基亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以68%的产率得到4-methyl-3-(perfluorophenyl)-1-(triisopropylsilyl)-1H-indole
  参考文献：
  名称：

  Au-Catalyzed Cross-Coupling of Arenes via Double C–H Activation

  摘要：

  The first methodology for Au(I/III)-catalyzed oxidative cross-coupling of arenes via double C-H activation has been developed. The reaction is fully selective for the cross-coupling between electron-rich hetero-/carbocyclic arenes and electron-poor arenes bearing relatively acidic C-H bonds: The inherently high cross-selectivity of the system obviates the need for directing groups or a large excess of one of the coupling partners.

  DOI：

  10.1021/jacs.5b10593
• 作为产物：
  描述：

  4-甲基吲哚 、 三异丙基氯硅烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 以90%的产率得到4-methyl-1-(triisopropylsilyl)-1H-indole
  参考文献：
  名称：

  Au-Catalyzed Cross-Coupling of Arenes via Double C–H Activation

  摘要：

  The first methodology for Au(I/III)-catalyzed oxidative cross-coupling of arenes via double C-H activation has been developed. The reaction is fully selective for the cross-coupling between electron-rich hetero-/carbocyclic arenes and electron-poor arenes bearing relatively acidic C-H bonds: The inherently high cross-selectivity of the system obviates the need for directing groups or a large excess of one of the coupling partners.

  DOI：

  10.1021/jacs.5b10593

文献信息

• Au-Catalyzed Cross-Coupling of Arenes via Double C–H Activation
  作者：Xacobe C. Cambeiro、Nanna Ahlsten、Igor Larrosa

  DOI：10.1021/jacs.5b10593

  日期：2015.12.23

  The first methodology for Au(I/III)-catalyzed oxidative cross-coupling of arenes via double C-H activation has been developed. The reaction is fully selective for the cross-coupling between electron-rich hetero-/carbocyclic arenes and electron-poor arenes bearing relatively acidic C-H bonds: The inherently high cross-selectivity of the system obviates the need for directing groups or a large excess of one of the coupling partners.