2-(fluoromethylthio)-6-fluoropyridine

• 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-(fluoromethylthio)-6-fluoropyridine
• 英文别名: 2-Fluoro-6-(fluoromethylsulfanyl)pyridine
• 化学式: C₆H₅F₂NS
• 分子量: 161.175
• InChiKey: UIPYRIVHLTXRIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-巯基吡啶 、 alkaline earth salt of/the/ methylsulfuric acid 在 四乙基氟化铵水合物 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 4.5h， 生成 2-(fluoromethylthio)-6-fluoropyridine
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 35.¹ Anodic Fluorination of 2-Pyrimidyl, 2-Pyridyl, and 2-Quinazolinonyl Sulfides

  摘要：

  Highly regioselective electrochemical fluorination of 2-pyrimidyl sulfides having an electron(EWG) withdrawing group at the position alpha to the sulfur atom was successfully carried out using Et4NF . nHF (n = 3, 4) or Et3N . 3HF as a supporting electrolyte and a fluoride ion source in 1,2-dimethoxyethane (DME) in an undivided cell. 2-Methylthiopyrimidine devoid of an EWG was also selectively fluorinated in DME to provide 2-(fluoromethylthio)pyrimidine in a moderate yield as 63%, while corresponding 2-methylthiopyridine was less selectively fluorinated in lower yield along with alpha,alpha-difluorinated product. In contrast, the corresponding 2-quinazolinonyl sulfides underwent similarly alpha-fluorination along with unexpected ipso-fluorination through anodic desulfurization.

  DOI：

  10.1021/jo9909857