2-perfluorohexylthiothiazoline | 135285-24-4

• 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-perfluorohexylthiothiazoline
• CAS: 135285-24-4
• 化学式: C₉H₂F₁₃NS₂
• 分子量: 435.233
• InChiKey: QXUQMXOSWRABJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  全氟己基碘烷 、 Thiazole-2-thiolatetetramethyl-ammonium; 在 N,N,N,N-tetraethylammonium tetrafluoroborate 、 对硝基苯甲腈 作用下， 以 乙腈 为溶剂， 以48%的产率得到2-perfluorohexylthiothiazoline
  参考文献：
  名称：

  Electrochemically induced nucleophilic substitution of perfluoroalkyl halides. An example of a dissociative electron-transfer-induced chemical reaction

  摘要：

  Nucleophilic substitution of perfluoroalkyl halides can be induced electrochemically. The reaction mechanism is a slightly modified version of the classical S(RN)1 mechanism in which the reaction is triggered by dissociative electron transfer, not involving the intermediacy of the anion radical of the substrate. Direct electrochemical induction is possible in principle with the iodides but not with the bromides because the reduction potentials of the substrate and of the perfluoroalkyl radical are too close in the latter case. This impossibility can be overcome by using as inductor an electrochemically generated outer-sphere electron donor. Thiolates react at the sulfur atom whereas phenoxide as well as imidazolate ions react at ring carbons rather than at the negatively charged heteroatom.

  DOI：

  10.1021/ja00018a025