(R)-2-methyl-2-(methanesulfonyloxy)hexanitrile | 240435-40-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (R)-2-methyl-2-(methanesulfonyloxy)hexanitrile
• 英文别名: [(2R)-2-cyanohexan-2-yl] methanesulfonate
• CAS: 240435-40-9
• 化学式: C₈H₁₅NO₃S
• 分子量: 205.278
• InChiKey: YADQMWDJPKGYNS-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  硫代乙酸 、 (R)-2-methyl-2-(methanesulfonyloxy)hexanitrile 在 2,3,5-三甲基吡啶 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以84%的产率得到(S)-2-acetylthio-2-methylhexanenitrile
  参考文献：
  名称：

  Stereoselective substitution of (R)-2-(sulfonyloxy)nitriles with sulfur nucleophiles

  摘要：

  Optically active 2-(4-toluenesulfonyloxy)- and (4-nitrobenzenesulfonyloxy)nitriles (R)-3 and (R)-4, which were obtained from (R)-cyanohydrins (R)-2 by sulfonylation, react with sulfur nucleophiles such as potassium thioacetate, potassium ethylxanthogenate, potassium thiocyanate, as well as thioalcohols and thiophenol in a typical S(N)2 manner to give the (S)-2-sulfanyl nitriles (S)-7-9 and (S)-11-13 in good chemical yields and enantiomeric excesses. Even (R)-2-methyl-2-(methanesulfonyloxy)hexanenitrile (R)-6, derived from ketone cyanohydrin (R)-5, reacts with potassium thioacetate to yield (S)-2-acetylthio-2-methylhexanenitrile (S)-10 with 97% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00154-8
• 作为产物：
  描述：

  2-己酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 almond meal 、 citrate buffer pH 4.0 作用下， 以 various solvent(s) 为溶剂， 反应 78.0h， 生成 (R)-2-methyl-2-(methanesulfonyloxy)hexanitrile
  参考文献：
  名称：

  Stereoselective substitution of (R)-2-(sulfonyloxy)nitriles with sulfur nucleophiles

  摘要：

  Optically active 2-(4-toluenesulfonyloxy)- and (4-nitrobenzenesulfonyloxy)nitriles (R)-3 and (R)-4, which were obtained from (R)-cyanohydrins (R)-2 by sulfonylation, react with sulfur nucleophiles such as potassium thioacetate, potassium ethylxanthogenate, potassium thiocyanate, as well as thioalcohols and thiophenol in a typical S(N)2 manner to give the (S)-2-sulfanyl nitriles (S)-7-9 and (S)-11-13 in good chemical yields and enantiomeric excesses. Even (R)-2-methyl-2-(methanesulfonyloxy)hexanenitrile (R)-6, derived from ketone cyanohydrin (R)-5, reacts with potassium thioacetate to yield (S)-2-acetylthio-2-methylhexanenitrile (S)-10 with 97% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00154-8