N-methyl-3-(2-pridyl)thio-1H-indole

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-methyl-3-(2-pridyl)thio-1H-indole
• 英文别名: 3-(2-pyridylthio)-1-methylindole；1-methyl-3-(pyridin-2-ylthio)-1H-indole；1-Methyl-3-pyridin-2-ylsulfanylindole
• 化学式: C₁₄H₁₂N₂S
• 分子量: 240.329
• InChiKey: RLLFBBCTXBCRES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-甲基吲哚 、 2,2'-二硫二吡啶 在 silver nitrate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以86%的产率得到N-methyl-3-(2-pridyl)thio-1H-indole
  参考文献：
  名称：

  银介导的吲哚和苯并咪唑与二（杂）芳基二硫化物的磺酰化

  摘要：

  An efficient synthesis of novel sulfenylated N-heterocycles derivatives via AgNO3 mediated C-S coupling reaction has been developed. This reaction could be carried out under mild reaction conditions with straightforward operation and good yield. A wide range of substrates can be utilized for the C-S coupling reaction giving sulfenylated indoles and benzimidazoles, which are the importance of frameworks in medicinal and synthetic chemistry.

  DOI：

  10.3987/com-16-13641

文献信息

• Oxone‐Mediated Oxidative 3‐Arylthio Substitution of Indoles
  作者：Guaili Wu、Jing Wu、Jialiang Wu、Longmin Wu

  DOI：10.1080/00397910701860174

  日期：2008.3.1

  Abstract Oxone‐mediated oxidative 3‐arylthio substitution of indoles with benzenethiols in methanol has been succeeded, giving 3‐arylthioindoles. Indoles bearing a 2‐methyl group particularly exhibited higher activities toward 3‐arylthio substitutions. 3‐(2′‐Pyridylthio)indoles used as selective COX‐2 inhibitors were prepared in good to excellent yields.

  摘要 Oxone 介导的吲哚与苯硫醇在甲醇中的氧化 3-芳硫基取代已经成功，得到 3-芳硫基吲哚。带有 2-甲基的吲哚尤其对 3-芳硫基取代表现出更高的活性。用作选择性 COX-2 抑制剂的 3-(2'-Pyridylthio) 吲哚的收率很好。
• Development of a Novel, Highly Efficient Halide-Catalyzed Sulfenylation of Indoles
  作者：Matthew Tudge、Minoru Tamiya、Cecile Savarin、Guy R. Humphrey

  DOI：10.1021/ol052615c

  日期：2006.2.1

  The reaction of a variety of indoles with N-thioalkyl- and N-thioarylphthalimides to produce 3-thioindoles is reported. Catalytic quantities of halide-containing salts are crucial to the success of this reaction. This highly efficient reaction provides sulfenylated indoles from bench-stable, readily available starting materials in good to excellent yields.
• Silver-Mediated Sulfenylation of Indoles and Benzimidazoles with Di(hetero)aryl Disulfides
  作者：Xi-Cun Wang、Wen-Juan Wang

  DOI：10.3987/com-16-13641

  日期：——

  An efficient synthesis of novel sulfenylated N-heterocycles derivatives via AgNO3 mediated C-S coupling reaction has been developed. This reaction could be carried out under mild reaction conditions with straightforward operation and good yield. A wide range of substrates can be utilized for the C-S coupling reaction giving sulfenylated indoles and benzimidazoles, which are the importance of frameworks in medicinal and synthetic chemistry.