(R)-3-hydroxy-2-phenylpropanoic acid compound with (R)-tert-butyl(phenyl)phosphine oxide (1:1) | 1217298-44-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (R)-3-hydroxy-2-phenylpropanoic acid compound with (R)-tert-butyl(phenyl)phosphine oxide (1:1)
• CAS: 1217298-44-6
• 化学式: C₉H₁₀O₃*C₁₀H₁₅OP
• 分子量: 348.379
• InChiKey: XVCLSDPIKQZQMC-WDBKTSHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  DL-托品酸 、 tert-Butylphenylphosphine oxide 以 乙醚 为溶剂， 反应 12.0h， 生成 (S)-3-hydroxy-2-phenylpropanoic acid compound with (R)-tert-butyl(phenyl)phosphine oxide (1:1) 、 (R)-3-hydroxy-2-phenylpropanoic acid compound with (R)-tert-butyl(phenyl)phosphine oxide (1:1)
  参考文献：
  名称：

  Enantiopure tert-butyl(phenyl)phosphine oxide. Chirality-recognition ability and mechanism

  摘要：

  When enantiopure tert-butyl(phenyl)phosphine oxide 1 was used as a resolving agent, it showed an acceptable to good chirality-recognition ability for several kinds of racemic carboxylic acids 2. A study on a chirality-recognition mechanism based on X-ray crystallographic analyses of the diastereomeric complexes of 2 with 1 revealed that the complex crystals consisted of helical columns and that 1 was not responsible for the formation of the helical column and occupied a void between the columns; although I interacted with 2 via a hydrogen bond to primarily form a pair with 2, the complex crystals were mainly stabilized by the accumulation of weak interactions, such as CH/pi, pi/pi and CH center dot center dot center dot O interactions, between 1/1, 1/2 and 2/2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.021