2-(methylthio)-1-(pyridin-2-yl)-1H-benzo[d]imidazole | 1120329-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(methylthio)-1-(pyridin-2-yl)-1H-benzo[d]imidazole
• 英文别名: 2-(methylthio)-1-(pyridin-2-yl)benzimidazole；2-Methylsulfanyl-1-pyridin-2-ylbenzimidazole
• CAS: 1120329-16-9
• 化学式: C₁₃H₁₁N₃S
• 分子量: 241.316
• InChiKey: RGXRULGHNDXFHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 copper(l) iodide 、 1,10-菲罗啉 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 2-(methylthio)-1-(pyridin-2-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Copper(I)-Catalyzed Synthesis of Substituted 2-Mercapto Benzimidazoles

  摘要：

  An efficient method for the preparation of various substituted 2-mercapto benzimidazoles from their corresponding thioureas has been developed. S-Alkylation of thioureas followed by Cu-catalyzed intramolecular N-arylation furnished substituted 2-mercapto benzimidazoles in high yields and short reaction times. Furthermore, 2-mercapto benzimidazoles substituted with a p-methoxybenzyl group allowed access to benzimidazole thiones.

  DOI：

  10.1021/jo802589d

文献信息

• Copper Acetate–DMSO Promoted Methylthiolation of Arenes and Heteroarenes
  作者：Poonam Sharma、Sandeep Rohilla、Nidhi Jain

  DOI：10.1021/acs.joc.5b00443

  日期：2015.4.17

  An unprecedented copper acetate–DMSO promoted methylthiolation of arenes and heteroarenes in the presence of air has been developed. The reaction is highly regioselective under the directing group influence of pyridine and pyrimidine functional units and gives the thiomethylated product in moderate to high yields.

  在空气存在下，空前的乙酸铜-DMSO促进了芳烃和杂芳烃的甲基硫醇化。该反应在吡啶和嘧啶官能团的直接基团的影响下具有高度的区域选择性，并以中等至高收率得到了硫代甲基化的产物。