2-methyl-1,3-dithiane S,S,S,S-tetraoxide | 86365-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2-methyl-1,3-dithiane S,S,S,S-tetraoxide
• 英文别名: 2-methyl-[1,3]dithiane-1,1,3,3-tetraoxide；2-Methyl-[1,3]dithian-1,1,3,3-tetraoxid；2-Methyl-1,3-dithiane 1,1,3,3-tetraoxide
• CAS: 86365-47-1
• 化学式: C₅H₁₀O₄S₂
• 分子量: 198.264
• InChiKey: HKUYPZNYAFFKLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  264 °C
• 沸点：
  516.5±43.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-1,3-dithiane S,S,S,S-tetraoxide 、 乙醇 、 sodium ethanolate 、 氯化苄 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Autenrieth; Wolff, Chemische Berichte, 1899, vol. 32, p. 1373

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-1,3-二噻烷 在 HOF* CH₃CN 作用下， 以 氯仿 、 水 为溶剂， 以95%的产率得到2-methyl-1,3-dithiane S,S,S,S-tetraoxide
  参考文献：
  名称：

  Oxidation of Sulfur-Containing Compounds with HOF·CH₃CN

  摘要：

  The HOF . CH3CN complex, easily prepared by passing F-2 through aqueous acetonitrile, is an exceptionally efficient oxygen transfer agent. All types of sulfides have been oxidized to sulfones in excellent yields, in a few minutes at room temperature. The reaction proceeds through the formation of sulfoxides which at low temperatures of around -75 degrees C could be isolated in good yields. It was demonstrated through a reaction with thianthrene 5-oxide (20) that HOF . CH3CN is strongly electrophilic in nature. Sulfides with an electron-depleted sulfur atom such as perfluoroalkyl or aryl sulfides, which could not be well oxidized by any other method, were also efficiently converted to the corresponding sulfones in minutes. Thiophenes are generally hard to oxidize to the corresponding S-dioxides since the conditions required by the orthodox oxidants encourage consecutive typical ene and diene reactions. HOF . CH3CN requires;short reaction times and low temperatures, thus enabling the isolation of thiophene dioxides, some of which could not be made by any other way. It seems that apart from unprotected amines, other functional groups such as aromatic rings, ketones, hydroxyls, and ethers do not interfere, since the sulfur atom reacts considerably faster.

  DOI：

  10.1021/jo961862e