threo-2-methyl-3-(phenylthio)butyronitrile | 110720-49-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: threo-2-methyl-3-(phenylthio)butyronitrile
• 英文别名: (2S,3R)-2-methyl-3-phenylsulfanylbutanenitrile
• CAS: 110720-49-5；110720-50-8
• 化学式: C₁₁H₁₃NS
• 分子量: 191.297
• InChiKey: ULLYSXJYMGYFIP-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z)-2-甲基-2-丁烯腈 、 苯硫酚 在 正丁基锂 作用下， 生成 erythro-2-methyl-3-(phenylthio)butyronitrile 、 threo-2-methyl-3-(phenylthio)butyronitrile
  参考文献：
  名称：

  Stereospecific nucleophilic addition reactions to olefins. Addition of thiols to .alpha.,.beta.-unsaturated carboxylic acid derivatives

  摘要：

  Stereospecific nucleophilic addition of thiols to derivatives of alpha,beta-unsaturated carboxylic acids is described. The additions are carried out at room temperature in the presence of a catalytic amount of lithium thiolate and an excess of thiol as a proton source. Erythro and threo adducts are obtained with high diasteroselectivity from E and Z olefins, respectively. This anti addition suggests that the enolate generated by nucleophilic addition undergoes rapid protonation prior to conformational change in the intermediate.

  DOI：

  10.1021/jo00023a021

文献信息

• Stereospecific nucleophilic addition reactions to olefins. Addition of thiols to .alpha.,.beta.-unsaturated carboxylic acid derivatives
  作者：Okiko Miyata、Tetsuro Shinada、Ichiya Ninomiya、Takeaki Naito、Tadamasa Date、Kimio Okamura、Satoshi Inagaki

  DOI：10.1021/jo00023a021

  日期：1991.11

  Stereospecific nucleophilic addition of thiols to derivatives of alpha,beta-unsaturated carboxylic acids is described. The additions are carried out at room temperature in the presence of a catalytic amount of lithium thiolate and an excess of thiol as a proton source. Erythro and threo adducts are obtained with high diasteroselectivity from E and Z olefins, respectively. This anti addition suggests that the enolate generated by nucleophilic addition undergoes rapid protonation prior to conformational change in the intermediate.