2-(phenylthio)-3-[(phenylthio)(trimethylsilyl)-methyl]-1H-indole | 247222-88-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(phenylthio)-3-[(phenylthio)(trimethylsilyl)-methyl]-1H-indole
• 英文别名: 2-phenylsulfanyl-3-[phenylsulfanyl-(trimethyl-silanyl)-methyl]-1H-indole；trimethyl-[phenylsulfanyl-(2-phenylsulfanyl-1H-indol-3-yl)methyl]silane
• CAS: 247222-88-4
• 化学式: C₂₄H₂₅NS₂Si
• 分子量: 419.687
• InChiKey: KQHLVKVJFVKQGV-UHFFFAOYSA-N

物化性质

• 沸点：
  541.7±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.03
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(phenylthio)-3-[(phenylthio)(trimethylsilyl)-methyl]-1H-indole 在 potassium fluoride 、 dirhodium tetraacetate 、 18-冠醚-6 作用下， 以 乙腈 、 苯 为溶剂， 反应 12.0h， 生成 2-(3-Ethylsulfanylmethyl-1H-indol-2-yl)-3-oxo-2-phenylsulfanyl-butyric acid ethyl ester
  参考文献：
  名称：

  The Use of Sulfur Ylides in the Synthesis of Substituted Indoles

  摘要：

  [GRAPHICS]This letter describes the insertion of rhodium carbenoids into thioindoles, C-10 thioindoles undergo fragmentation-coupling reactions when exposed to rhodium carbenoids. In an analogous fashion, ketoester- and malonate-substituted carbenoids have been found to insert into C-2 thioindoles, In contrast, vinylogous carbenoids were found to alkylate C-2 thioindoles at C-3.

  DOI：

  10.1021/ol0162320
• 作为产物：
  描述：

  N-[2-(2-三甲基硅乙炔基)苯基]甲酰胺 在 偶氮二异丁腈 、 二异丙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 2-(phenylthio)-3-[(phenylthio)(trimethylsilyl)-methyl]-1H-indole
  参考文献：
  名称：

  Cascades to Substituted Indoles

  摘要：

  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.

  DOI：

  10.1021/jo000831n

文献信息

• Sulfur Ylide-Initiated Thio-Claisen Rearrangements. The Synthesis of Highly Substituted Indolines
  作者：Alexei V. Novikov、Abigail R. Kennedy、Jon D. Rainier

  DOI：10.1021/jo026582f

  日期：2003.2.1

  The coupling of rhodium carbenoids from vinyl diazoacetates with 2-thio-3-alkyl indoles was found to generate C(3) quaternary substituted indolines via a thionium ylide-initiated [3,3]-sigmatropic rearrangement.

  铑类胡萝卜素从重氮乙酸乙烯酯与2-thio-3-烷基吲哚的偶联被发现通过硫鎓叶立德引发的[3,3]-σ重排产生C（3）季取代的二氢吲哚。
• 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.
• The Use of Sulfur Ylides in the Synthesis of Substituted Indoles
  作者：Abigail R. Kennedy、Michael H. Taday、Jon D. Rainier

  DOI：10.1021/ol0162320

  日期：2001.7.1

  [GRAPHICS]This letter describes the insertion of rhodium carbenoids into thioindoles, C-10 thioindoles undergo fragmentation-coupling reactions when exposed to rhodium carbenoids. In an analogous fashion, ketoester- and malonate-substituted carbenoids have been found to insert into C-2 thioindoles, In contrast, vinylogous carbenoids were found to alkylate C-2 thioindoles at C-3.
• 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.