[ethylsulfanyl-(2-ethylsulfanyl-1H-indol-3-yl)methyl]-trimethylsilane | 247222-86-2

• 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: [ethylsulfanyl-(2-ethylsulfanyl-1H-indol-3-yl)methyl]-trimethylsilane
• CAS: 247222-86-2
• 化学式: C₁₆H₂₅NS₂Si
• 分子量: 323.599
• InChiKey: SKHSGTDQQBBYOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  [ethylsulfanyl-(2-ethylsulfanyl-1H-indol-3-yl)methyl]-trimethylsilane 在 potassium fluoride 、 dirhodium tetraacetate 、 18-冠醚-6 作用下， 以 乙腈 、 苯 为溶剂， 生成 dimethyl 2-[[3-[(E)-5-ethoxy-5-oxopent-3-en-2-yl]-2-ethylsulfanylindol-3-yl]methyl]propanedioate
  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-formyl-2-iodoaniline 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 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 [ethylsulfanyl-(2-ethylsulfanyl-1H-indol-3-yl)methyl]-trimethylsilane
  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

• 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.