3-(trimethylsilylmethyl)indole | 152592-93-3

• 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: 3-(trimethylsilylmethyl)indole
• 英文别名: 1H-indol-3-ylmethyl(trimethyl)silane
• CAS: 152592-93-3
• 化学式: C₁₂H₁₇NSi
• 分子量: 203.359
• InChiKey: NJUYCUWRMXOZMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  六羰基铬 、 3-(trimethylsilylmethyl)indole 以 1,4-二氧六环 为溶剂， 以84%的产率得到carbon monoxide;chromium;1H-indol-3-ylmethyl(trimethyl)silane
  参考文献：
  名称：

  New substitution reactions on indole promoted by the Cr(CO)3 unit

  摘要：

  DOI：

  10.1016/s0022-328x(00)93987-1
• 作为产物：
  描述：

  2-(trimethylsilylethynyl)-1-isocyanobenzene 在 偶氮二异丁腈 、 三正丁基氢锡 、 oxonium 作用下， 以 苯 为溶剂， 以82%的产率得到3-(trimethylsilylmethyl)indole
  参考文献：
  名称：

  An isonitrile-alkyne cascade to di-substituted indoles

  摘要：

  Intramolecular tin and sulfur mediated free-radical cyclizations between an aryl isonitrile and a pendant TMS-substituted alkyne give 2,3-disubstituted indoles from 5-exo-dig cyclization and nucleophilic trapping of the resulting indolenine intermediate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01169-7

文献信息

• An isonitrile-alkyne cascade to di-substituted indoles
  作者：Jon D. Rainier、Abigail R. Kennedy、Eric Chase

  DOI：10.1016/s0040-4039(99)01169-7

  日期：1999.8

  Intramolecular tin and sulfur mediated free-radical cyclizations between an aryl isonitrile and a pendant TMS-substituted alkyne give 2,3-disubstituted indoles from 5-exo-dig cyclization and nucleophilic trapping of the resulting indolenine intermediate. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of (Indol-3-ylmethyl)trimethylsilanes by Means of Alumina-Mediated Alkylation of Indoles with α-Chloro-α-silylsulfides
  作者：Hiroyuki Ishibashi、Kayo Nishida、Masazumi Ikeda

  DOI：10.1080/00397919308011123

  日期：1993.9

  Treatment of a mixture of indoles and alpha-chloro-alpha-silylsulfide 6 with neutral chromatographic alumina afforded the aromatic substitution products 8, which were desurfurized with Bu3SnH and AIBN to give (indol-3-ylmethyl)trimethylsilanes 9.
• Cascades to Substituted Indoles
  作者：Jon D. Rainier、Abigail R. Kennedy

  DOI：10.1021/jo000831n

  日期：2000.9.1

  This paper describes the synthesis of dithioindoles from the free-radical cyclizations of arylisonitriles having pendant alkynes. Also described is the synthesis of substituted indoles and spiro-fused indoles from the coupling of dithioindoles with active hydrogen-containing compounds.
• New substitution reactions on indole promoted by the Cr(CO)3 unit
  作者：M.F Semmelhack、W Wulff、J.L Garcia

  DOI：10.1016/s0022-328x(00)93987-1

  日期：1982.12