ethyl [1-(4-bromophenyl)-1-hydroxy-3-oxobutyl](phenyl)phosphinate | 1207386-87-5

• 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 [1-(4-bromophenyl)-1-hydroxy-3-oxobutyl](phenyl)phosphinate
• 英文别名: (4S)-4-(4-bromophenyl)-4-[ethoxy(phenyl)phosphoryl]-4-hydroxybutan-2-one
• CAS: 1207386-87-5
• 化学式: C₁₈H₂₀BrO₄P
• 分子量: 411.232
• InChiKey: QHCISXYIAWBPOB-UUOWRZLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl (4-bromobenzoyl)phenylphosphinate 、 丙酮 在 D-脯氨酸 、 水 作用下， 反应 120.0h， 以70%的产率得到ethyl [1-(4-bromophenyl)-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

文献信息

• Organocatalytic Enantioselective Synthesis of Both Diastereomers of α-Hydroxyphosphinates
  作者：Sampak Samanta、Sandun Perera、Cong-Gui Zhao

  DOI：10.1021/jo9022099

  日期：2010.2.19

  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.