2-hydroxy-(4'-methoxyphenyl)-3-methylbutanoic acid | 91555-51-0

• 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: 2-hydroxy-(4'-methoxyphenyl)-3-methylbutanoic acid
• 英文别名: α-(p-Methoxyphenyl)-α-isopropyllglycolsaeure；2-Hydroxy-2-(4-methoxyphenyl)-3-methylbutanoic acid；2-hydroxy-2-(4-methoxyphenyl)-3-methylbutanoic acid
• CAS: 91555-51-0
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: BEPOADHONAHASS-UHFFFAOYSA-N

物化性质

• 熔点：
  137 °C
• 沸点：
  385.3±32.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-(4'-methoxyphenyl)-3-methylbutanoic acid 在 (NMe₄)Co(III)Me₂opba*2H₂O*CH₃CN 、 氧气 、 特戊醛 作用下， 以 乙腈 为溶剂， 反应 5.5h， 以90%的产率得到p-甲氧基异苯丁酮
  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：

  methyl 2-hydroxy-2-(4-methoxyphenyl)acetate 在 氢氧化钾 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-hydroxy-(4'-methoxyphenyl)-3-methylbutanoic acid
  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

文献信息

• Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation
  作者：Shasha Xie、Defang Li、Hanchu Huang、Fuyuan Zhang、Yiyun Chen

  DOI：10.1021/jacs.9b09099

  日期：2019.10.16

  α-ketoacids enabled by the Lewis acid activation. The in situ boron complex formation is confirmed by various spectroscopic measurements and mechanistic probing experiments, which facilitates various alkyl boronic acid addition to the carbonyl group and prevents the cleavage of the newly-formed C-C bond. Diversely substituted lactates can be synthesized from readily available alkyl boronic acids and ketoacids

  由于所得烷氧基自由基容易断裂，分子间自由基加成到羰基上是困难的。迄今为止，酮的分子间自由基加成是构建季碳中心的一种有价值的方法，仍然是一项艰巨的合成挑战。在这里，我们报告了第一个可见光诱导的分子间烷基硼酸加成到 α-酮酸通过路易斯酸活化实现的。各种光谱测量和机械探测实验证实了原位硼配合物的形成，这有助于将各种烷基硼酸加成到羰基上，并防止新形成的 CC 键断裂。在室温下，仅在可见光照射下，无需任何额外试剂，即可由易得的烷基硼酸和酮酸合成不同取代的乳酸酯。这种硼活化方法可以扩展到作为自由基前体的烷基二氢吡啶与用于伯、仲和叔烷基自由基加成的外部硼试剂。在流动反应器中的无金属条件下，药学上有用的抗胆碱能前体很容易放大到数克。
• 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.