ethyl phenyl(propionyl)phosphinate | 1207386-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl phenyl(propionyl)phosphinate
• 英文别名: 1-[Ethoxy(phenyl)phosphoryl]propan-1-one
• CAS: 1207386-97-7
• 化学式: C₁₁H₁₅O₃P
• 分子量: 226.212
• InChiKey: UYSGJEJAPPSIKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl phenyl(propionyl)phosphinate 、 丙酮 在 L-脯氨酸 、 水 作用下， 反应 40.0h， 生成 ethyl (1-ethyl-1-hydroxy-3-oxobutyl)(phenyl)phosphinate 、 ethyl (1-ethyl-1-hydroxy-3-oxobutyl)(phenyl)phosphinate 、 ethyl (1-ethyl-1-hydroxy-3-oxobutyl)(phenyl)phosphinate 、 ethyl (1-ethyl-1-hydroxy-3-oxobutyl)(phenyl)phosphinate
  参考文献：
  名称：

  Organocatalytic Enantioselective Synthesis of Both Diastereomers of α-Hydroxyphosphinates

  摘要：

  Racemic alpha-acylphosphinates and formylphosphinate hydrate were used directly as the substrates in a proline derivative-catalyzed cross aldol reaction with ketones. Because of the preexisting phosphorus stereogenic center, a mixture of two diastereomers of the corresponding alpha-hydroxyphosphinates was obtained in this reaction. Good to high enantioselectivities (up to 99% ee) were obtained simultaneously for the two diastereomers in good yields. Good diastereoselectivities were also obtained when the reaction generates an additional carbon stereogenic center.

  DOI：

  10.1021/jo9022099