3-(2-吡啶基硫代)-2-甲基吲哚 | 1021422-62-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 3-(2-吡啶基硫代)-2-甲基吲哚
• 英文名称: 2-methyl-3-(pyridin-2-ylthio)-1H-indole
• 英文别名: 2-methyl-3-pyridin-2-ylsulfanyl-1H-indole
• CAS: 1021422-62-7
• 化学式: C₁₄H₁₂N₂S
• 分子量: 240.329
• InChiKey: XEILZBCJHFANDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  54
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 、 2,2'-二硫二吡啶 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以83%的产率得到3-(2-吡啶基硫代)-2-甲基吲哚
  参考文献：
  名称：

  吲哚和二芳基二硫化物的可见光促进3-芳基硫代吲哚的合成

  摘要：

  可以通过吲哚和二硫化物的光辐射以高收率合成3-芳硫基吲哚。催化量的碘化钠可有效地促进反应。提出了涉及用芳基亚硫基碘中间体亲电取代吲哚的反应机理。

  DOI：

  10.1016/j.tetlet.2017.05.090

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。
• 一种电化学催化氧化合成3-巯基吲哚类化合 物的方法
  申请人：浙江工业大学

  公开号：CN107620088B

  公开（公告）日：2019-05-07

  本发明公开了一种电化学催化氧化合成3‑巯基吲哚类化合物的方法，采用三电极体系，阴极和阳极均为石墨电极，以0.1mol/L的硝酸银乙腈溶液作为参比电极；在四氟硼酸钠乙腈溶液中，加入吲哚类化合物、二硫醚和碘化钾，在温度45～75℃、0.2～0.6V的恒压条件下搅拌电解反应3～24h后，反应液经后处理得到产物3‑巯基吲哚类化合物。本发明所述的合成方法，操作简便安全，产物3‑巯基吲哚类化合物收率高；反应条件比较温和；使用了清洁的电能为氧化还原剂，大大降低了环境成本。
• Visible-light promoted synthesis of 3-arylthioindoles from indoles and diaryl disulfides
  作者：Lin-miao Ye、Jie Chen、Peng Mao、Xue-jing Zhang、Ming Yan

  DOI：10.1016/j.tetlet.2017.05.090

  日期：2017.7

  3-Arylthioindoles could be synthesized in good yields via the photoirradiation of indoles and disulfides. The reaction is efficiently promoted by the catalytic amount of sodium iodide. A reaction mechanism involving the electrophilic substitution of indoles with arylsulfenyl iodine intermediates is suggested.

  可以通过吲哚和二硫化物的光辐射以高收率合成3-芳硫基吲哚。催化量的碘化钠可有效地促进反应。提出了涉及用芳基亚硫基碘中间体亲电取代吲哚的反应机理。
• 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.
• Electrochemical Sulfenylation of Indoles with Disulfides Mediated by Potassium Iodide
  作者：Chen Chen、Pengfei Niu、Zhenlu Shen、Meichao Li

  DOI：10.1149/2.0071807jes

  日期：——

  A novel electrochemical system for sulfenylation of indoles with disulfides to generate 3-sulfenylindoles via C-S bond formation mediated by potassium iodide at a low potential was developed. Iodine was electrogenerated from iodide ions at a graphite anode and showed a high catalytic activity for the electrochemical sulfenylation reactions. A variety of aromatic, heteroaromatic and aliphatic disulfides could react with 2-methlyindole to synthesize the corresponding 3-sulfenylindoles in good to excellent yields. In addition, protected and unprotected indoles with various groups, especially electron-donating groups, also performed well in the sulfenylation reactions. The transformation, which proceeded through the redox of iodine and the generation of intermediate 3-iodoindole, provided an efficient and environmentally benign protocol for the synthesis of 3-sulfenylindoles under mild conditions. (C) 2018 The Electrochemical Society.