1-ethyl-2-(methyldithio)pyridinium tetraphenylborate | 136911-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-ethyl-2-(methyldithio)pyridinium tetraphenylborate
• CAS: 136911-98-3
• 化学式: C₈H₁₂NS₂*C₂₄H₂₀B
• 分子量: 505.556
• InChiKey: RVNRAXRWYFLQSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  3.88
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  巯基胆固醇 、 1-ethyl-2-(methyldithio)pyridinium tetraphenylborate 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以177 mg的产率得到(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-3-methyldisulfanyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
  参考文献：
  名称：

  A new procedure for the conversion of thiols into reactive sulfenylating agents

  摘要：

  Thiols may be converted in high yield into unsymmetrical 2-pyridyl disulfides 3. Treatment of these with alkylating agents (e.g., alkyl fluorosulfonates or oxonium salts) affords the corresponding N-alkylpyridyl disulfides 4, which are potent sulfenylating agents (Scheme II) and react smoothly with a variety of sulfur nucleophiles (e.g., thiols, thiones, thioamides, dithiocarbamates, thiocyanate, etc.) to afford disulfides, with amines to afford sulfenamides, and with beta-diketones to afford sulfides. This new method is particularly well-suited to the preparation of unsymmetrical disulfides and sulfenamides from complex and otherwise reactive thiols.

  DOI：

  10.1021/jo00023a039