anti-2-Methyl-3-phenyl-glutaric acid | 100786-66-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: anti-2-Methyl-3-phenyl-glutaric acid
• 英文别名: (2R,3R)-2-Methyl-3-phenylpentanedioic acid
• CAS: 100786-66-1
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: RSUWYAPAJXVXAU-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  anti-2-Methyl-3-phenyl-glutaric acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 0.25h， 生成 (2R,3R)-2-Methyl-3-phenyl-pentanedioyl dichloride
  参考文献：
  名称：

  Kinetic asymmetric protonation as a stereochemistry determining step in theMichael addition of acetic acid derivatives to ?-substituted cinnamic acid derivatives

  摘要：

  The reaction between acetic acid derivatives and alpha-substituted cinnamic acid derivatives has been studied in THF and THF:HMPT (80:20) as an alternative pathway of the Michael addition of phenylacetic and cinnamic acid derivatives. The regioselectivity observed is found to depend on the acceptor functional group and its geometry but not on the solvent used. The diastereoselectivity of the conjugate addition results from kinetic protonation of diastereotopic enolates (1,2-asymmetric induction). It varies from low in the presence of HMPT to considerable or even high in pure THF. The favoured anti or syn configuration in THF depends on the nature of the enolate. The results obtained are rationalized in terms of protonation via transition structures different in type (open us. chelated) and geometry.

  DOI：

  10.1007/bf00811020
• 作为产物：
  描述：

  (2R,3R)-2-phenylbutane-1,1,3-tricarboxylic acid 以91%的产率得到
  参考文献：
  名称：

  FRAHM, A. W., ARCH. PHARM., 1985, 318, N 11, 1009-1015

  摘要：

  DOI：