erythro-2-methyl-3-((phenylmethyl)thio)butanoic acid methyl ester | 137542-29-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: erythro-2-methyl-3-((phenylmethyl)thio)butanoic acid methyl ester
• 英文别名: methyl (2R,3R)-3-benzylsulfanyl-2-methylbutanoate
• CAS: 137542-29-1；137542-30-4
• 化学式: C₁₃H₁₈O₂S
• 分子量: 238.351
• InChiKey: SVUAEVJFSDOMKU-WDEREUQCSA-N

物化性质

• 沸点：
  328.0±25.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  erythro-2-methyl-3-((phenylmethyl)thio)butanoic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 生成 erythro-2-methyl-3((phenylmethyl)thio)butan-1-ol
  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
• 作为产物：
  描述：

  惕各酸甲酯 、 苄硫醇 在 正丁基锂 作用下， 生成 erythro-2-methyl-3-((phenylmethyl)thio)butanoic acid methyl ester
  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