2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]disulfanyl]-1H-benzimidazole | 136912-07-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]disulfanyl]-1H-benzimidazole
• CAS: 136912-07-7
• 化学式: C₃₄H₅₀N₂S₂
• 分子量: 550.916
• InChiKey: UDQZCCRRNLIKJA-NVYQQUOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  79.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  巯基胆固醇 在 溶剂黄146 作用下， 以 正己烷 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]disulfanyl]-1H-benzimidazole
  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