(Z)-3-(2-methyl-1-oxo-2-buten-1-yl)-2-oxazolidinone | 137542-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-3-(2-methyl-1-oxo-2-buten-1-yl)-2-oxazolidinone
• 英文别名: 3-[(Z)-2-methylbut-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 137542-43-9
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: AADSCRHWHRHAGN-UTCJRWHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-(2-methyl-1-oxo-2-buten-1-yl)-2-oxazolidinone 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 -2-methyl-3-(phenylthio)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：

  2-唑烷酮 、 (Z)-2-methyl-2-butenoyl chloride 生成 (Z)-3-(2-methyl-1-oxo-2-buten-1-yl)-2-oxazolidinone
  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