4-(2,6-dimethylphenoxy)-4-oxobutanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-(2,6-dimethylphenoxy)-4-oxobutanoic acid
• 英文别名: 4-(2,6-Dimethylphenoxy)-4-oxobutanoic acid
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: COJZGIGUNPKAJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2,6-dimethylphenoxy)-4-oxobutanoic acid 在 盐酸 、 氯化锆(IV) 作用下， 以 邻二氯苯 为溶剂， 反应 14.0h， 生成 4-(4-hydroxy-3,5-dimethylphenyl)-4-oxobutyric acid methyl ester
  参考文献：
  名称：

  Concise Synthesis of Photocleavable Molecular Tag for Laser Desorption Ionization Mass Spectrometry via Fries Reaction

  摘要：

  A new synthetic route for the photocleavable molecular tag for laser desorption ionization mass spectrometry (LDI-MS) was achieved using the Fries reaction of 2,6-dimethylphenyl ester as its key reaction. Zirconium chloride was used as uniquely efficient adjuvant to promote the reaction. The molecular tag was obtained in five steps without chromatographic purification. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.619678
• 作为产物：
  描述：

  丁二酸酐 、 2,6-二甲基苯酚 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到4-(2,6-dimethylphenoxy)-4-oxobutanoic acid
  参考文献：
  名称：

  The aldol addition reaction between γ-oxygenated carboxylic esters derived from 2,6-dimethylphenol and piperonal

  摘要：

  The stereoselectivity of the aldol addition reaction between gamma-oxygenated DMP-esters 1a-b and piperonal depends on the nature of the gamma-oxygenated substituent. A syn-diastereoselectivity was observed from 1a. This reverse selectivity is due to the chelation properties of the ketal moiety leading preferentially to the Z-enolate 7a by altering the transition state of the deprotonation step.

  DOI：

  10.1016/s0040-4039(00)76208-3