1-(triphenylsilyl)-1H-indole | 1256710-30-1

• 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-(triphenylsilyl)-1H-indole
• 英文别名: Ph3Si(C8H6N)；Indol-1-yl(triphenyl)silane；indol-1-yl(triphenyl)silane
• CAS: 1256710-30-1
• 化学式: C₂₆H₂₁NSi
• 分子量: 375.545
• InChiKey: ODIXZEOWJIVTGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  吲哚 、 三苯基硅烷 在 dirhodium tetraacetate 、 TBA₂WO₄ 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以46%的产率得到1-(triphenylsilyl)-1H-indole
  参考文献：
  名称：

  乙酸铑/碱催化氢硅烷与吲哚衍生物的N-甲硅烷基化。

  摘要：

  在铑（2）（OAc）（4）（OAC =乙酸盐）和TBA的存在下（2）WO（4）（TBA =四正丁基铵），吲哚衍生物与氢硅烷的N甲硅烷基化有效地进行到以高收率得到相应的N-甲硅烷基化的吲哚。吡咯并咔唑，也可为N-甲硅烷基化与所述组合的催化剂。

  DOI：

  10.1039/c2cc34381a

文献信息

• Rhodium acetate/base-catalyzed N-silylation of indole derivatives with hydrosilanes
  作者：Shintaro Itagaki、Keigo Kamata、Kazuya Yamaguchi、Noritaka Mizuno

  DOI：10.1039/c2cc34381a

  日期：——

  In the presence of Rh(2)(OAc)(4) (OAc = acetate) and TBA(2)WO(4) (TBA = tetra-n-butylammonium), the N-silylation of indole derivatives with hydrosilanes efficiently proceeded to give the corresponding N-silylated indoles in high yields. Pyrrole and carbazole were also N-silylated with the combined catalysts.

  在铑（2）（OAc）（4）（OAC =乙酸盐）和TBA的存在下（2）WO（4）（TBA =四正丁基铵），吲哚衍生物与氢硅烷的N甲硅烷基化有效地进行到以高收率得到相应的N-甲硅烷基化的吲哚。吡咯并咔唑，也可为N-甲硅烷基化与所述组合的催化剂。
• Synthesis, characterization and comparison of group 14 pyrrolides and indolides Ph3MX (M=Si, Ge, Sn; X=C4H4N, C8H6N)
  作者：Joël Poisson、Ivor Wharf、D. Scott Bohle、Mirela M. Barsan、Yuxuan Gu、Ian S. Butler

  DOI：10.1016/j.jorganchem.2010.07.029

  日期：2010.11

  The biologically important heterocycles pyrrole, C4H4N, and indole, C8H6N, ought to be useful as reagents in organic synthesis. Unfortunately, working with them has proved to be difficult because they tend to self-polymerize in solution, especially in the presence of acid catalysts. When the self-polymerization can be controlled, however, the pyrrole and indole units should provide an important route to selective N-metal binding, particularly when these ligands are activated by alkyl-lithium reagents. Using this approach, a general synthesis of the group 14 pyrrolides and indolides, Ph3MX (M = Si, Ge, Sn; X = C4H4N, C8H6N), has been developed and the results are reported here. The compounds are formed as high-melting, white crystalline solids and have been characterized by C-13-, Si-29- and Sn-119-NMR, Raman and electron-impact mass spectroscopy as well as elemental analysis. A single-crystal X-ray study of Ph3Si(C4H4N) has shown that the compound is disordered in the tetragonal lattice, even at low temperature (100 K). (C) 2010 Elsevier B. V. All rights reserved.
• Ru 3 (CO) 12 -catalyzed dehydrogenative Si N coupling of indoles with hydrosilanes without additive
  作者：Wenchao Zhai、Bin Li、Baiquan Wang

  DOI：10.1016/j.tet.2018.01.024

  日期：2018.3

  An efficient Ru3(CO)12-catalyzed dehydrogenative SiN coupling reaction of indoles, pyrrole, and carbazole with hydrosilanes is reported. The reaction does not need any external additive. This catalytic reaction has a wide substrate range, excellent functional group tolerance, and high to excellent reaction efficiency. Gram-scale synthesis demonstrates the practicability of this synthetic method.

  报道了吲哚，吡咯和咔唑与氢化硅烷的有效Ru 3（CO）12催化的脱氢Si N偶联反应。该反应不需要任何外部添加剂。该催化反应具有宽的底物范围，优异的官能团耐受性以及高至优异的反应效率。克级合成证明了这种合成方法的实用性。