2-hydroxy-2-phenylhexanedioic acid | 208041-42-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-hydroxy-2-phenylhexanedioic acid
• CAS: 208041-42-3
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: QNZIOIVENWHTGO-UHFFFAOYSA-N

物化性质

• 沸点：
  478.8±45.0 °C(Predicted)
• 密度：
  1.354±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-phenylhexanedioic acid 在 (NMe₄)Co(III)Me₂opba*2H₂O*CH₃CN 、 氧气 、 特戊醛 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以77%的产率得到4-苯甲酰基丁酸
  参考文献：
  名称：

  Nucleophilic benzoylation using lithiated methyl mandelate as a synthetic equivalent of the benzoyl carbanion. Oxidative decarboxylation of α-hydroxyacids

  摘要：

  The synthesis of alkyl aryl ketones using lithiated methyl mandelate as a synthetic equivalent of the benzoyl carbanion is reported (Umpolung). The methodology involves alkylation of methyl mandelate, hydrolysis of the ester group and oxidative decarboxylation of the resulting -alpha -hydroxyacids. The last step is carried out in a catalytic aerobic way using a Co(III) complex in the presence of pivalaldehyde under very mild and advantageous conditions. The procedure is also applied to methyl mandelates substituted on the aromatic ring. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01097-8
• 作为产物：
  描述：

  DL-扁桃酸甲酯 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 生成 2-hydroxy-2-phenylhexanedioic acid
  参考文献：
  名称：

  Catalytic aerobic oxidative decarboxylation of α-hydroxy-acids. Methyl mandelate as a benzoyl anion equivalent

  摘要：

  The monomeric square-planar cobalt(III) complex of bis-N,N'-disubstituted oxamides catalyses the oxidative decarboxylation of alpha-hydroxy acids with molecular oxygen/pivalaldehyde with very good yields. This reaction offers an interesting alternative in the use of methyl mandelate as a convenient benzoyl anion equivalent. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00482-1

文献信息

• Nucleophilic benzoylation using lithiated methyl mandelate as a synthetic equivalent of the benzoyl carbanion. Oxidative decarboxylation of α-hydroxyacids
  作者：Gonzalo Blay、Isabel Fernández、Pilar Formentin、Belén Monje、José R Pedro、Rafael Ruiz

  DOI：10.1016/s0040-4020(00)01097-8

  日期：2001.2

  The synthesis of alkyl aryl ketones using lithiated methyl mandelate as a synthetic equivalent of the benzoyl carbanion is reported (Umpolung). The methodology involves alkylation of methyl mandelate, hydrolysis of the ester group and oxidative decarboxylation of the resulting -alpha -hydroxyacids. The last step is carried out in a catalytic aerobic way using a Co(III) complex in the presence of pivalaldehyde under very mild and advantageous conditions. The procedure is also applied to methyl mandelates substituted on the aromatic ring. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Catalytic aerobic oxidative decarboxylation of α-hydroxy-acids. Methyl mandelate as a benzoyl anion equivalent
  作者：Gonzalo Blay、Isabel Fernández、Pilar Formentin、JoséR. Pedro、Antonio L. Roselló、Rafael Ruiz、Yves Journaux

  DOI：10.1016/s0040-4039(98)00482-1

  日期：1998.5

  The monomeric square-planar cobalt(III) complex of bis-N,N'-disubstituted oxamides catalyses the oxidative decarboxylation of alpha-hydroxy acids with molecular oxygen/pivalaldehyde with very good yields. This reaction offers an interesting alternative in the use of methyl mandelate as a convenient benzoyl anion equivalent. (C) 1998 Elsevier Science Ltd. All rights reserved.