8-methyl-10,10-diphenyl-5,10-dihydrobenzo[4,5]silolo[3,2-b]indole | 1167028-99-0

• 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: 8-methyl-10,10-diphenyl-5,10-dihydrobenzo[4,5]silolo[3,2-b]indole
• 英文别名: 5-methyl-10,10-diphenyl-10H-[1]benzosilolo[3,2-b][1]indole；5-Methyl-10,10-diphenyl-[1]benzosilolo[3,2-b]indole；5-methyl-10,10-diphenyl-[1]benzosilolo[3,2-b]indole
• CAS: 1167028-99-0
• 化学式: C₂₇H₂₁NSi
• 分子量: 387.556
• InChiKey: AXFNQGZSWJGAJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-methyl-3-(methyl(phenyl)silyl)-2-phenyl-1H-indole 在 [2,6-η6:η1-bis(2,4,6-trimethylphenyl)phenylthiolato]tris(4-fluorophenyl)phosphineruthenium(II)tetrakis[3,5-bis(trifluoromethyl)phenyl]borate 作用下， 以 氯苯 为溶剂， 反应 17.0h， 生成 8-methyl-10,10-diphenyl-5,10-dihydrobenzo[4,5]silolo[3,2-b]indole
  参考文献：
  名称：

  Catalytic Access to Indole-Fused Benzosiloles by 2-Fold Electrophilic C–H Silylation with Dihydrosilanes

  摘要：

  A protocol for the catalytic synthesis of indole-fused benzosiloles starting from 2-aryl-substituted indoles and dihydrosilanes is reported. Compared to known procedures, this method does not require prefunctionalized, starting materials and, hence, allows for a rapid access to those siloles. The net reaction is a 2-fold electrophilic C-H silylation catalyzed by cationic Ru-S complexes. Both reaction steps were separately investigated, and these results eventually led to the development of a two-step procedure. By preparing new Ru-S complexes with different weakly coordinating anions (WCAs), it is also shown that the latter can have a dramatic influence on the outcome of these reactions. Furthermore, the substrate scope of the new method is discussed.

  DOI：

  10.1021/acs.organomet.6b00801

文献信息

• Mochida, Kenji; Shimizu, Masaki; Hiyama, Tamejiro, Journal of the American Chemical Society, 2009, vol. 131, p. 8350 - 8351
  作者：Mochida, Kenji、Shimizu, Masaki、Hiyama, Tamejiro

  DOI：——

  日期：——
• Catalytic Access to Indole-Fused Benzosiloles by 2-Fold Electrophilic C–H Silylation with Dihydrosilanes
  作者：Lukas Omann、Martin Oestreich

  DOI：10.1021/acs.organomet.6b00801

  日期：2017.2.27

  A protocol for the catalytic synthesis of indole-fused benzosiloles starting from 2-aryl-substituted indoles and dihydrosilanes is reported. Compared to known procedures, this method does not require prefunctionalized, starting materials and, hence, allows for a rapid access to those siloles. The net reaction is a 2-fold electrophilic C-H silylation catalyzed by cationic Ru-S complexes. Both reaction steps were separately investigated, and these results eventually led to the development of a two-step procedure. By preparing new Ru-S complexes with different weakly coordinating anions (WCAs), it is also shown that the latter can have a dramatic influence on the outcome of these reactions. Furthermore, the substrate scope of the new method is discussed.