2-hydroxy-(4'-methoxyphenyl)-4-pentenoic acid | 334928-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-hydroxy-(4'-methoxyphenyl)-4-pentenoic acid
• 英文别名: 2-Hydroxy-2-(4-methoxyphenyl)pent-4-enoic acid；2-hydroxy-2-(4-methoxyphenyl)pent-4-enoic acid
• CAS: 334928-09-5
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: HYEZCRVEQTZHAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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)-4-pentenoic acid 在 (NMe₄)Co(III)Me₂opba*2H₂O*CH₃CN 、 氧气 、 特戊醛 作用下， 以 乙腈 为溶剂， 反应 9.0h， 以89%的产率得到1-(4-methoxyphenyl)but-3-en-1-one
  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)-4-pentenoic 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

• 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.