4-hydroxytetrafluorophenylacetic acid | 19225-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxytetrafluorophenylacetic acid
• 英文别名: 2,3,5,6-Tetrafluor-4-hydroxy-phenylessigsaeure；2,3,5,6-Tetrafluoro-4-hydroxybenzeneacetic acid；2-(2,3,5,6-tetrafluoro-4-hydroxyphenyl)acetic acid
• CAS: 19225-87-7
• 化学式: C₈H₄F₄O₃
• 分子量: 224.112
• InChiKey: GESIZZKEAALDEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-(4-(benzyloxy)-2,3,5,6-tetrafluorophenyl)-2-oxoethyl 4-((tert-butoxycarbonyl)amino)butanoate 在 palladium 10% on activated carbon 、 水 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 4-hydroxytetrafluorophenylacetic acid
  参考文献：
  名称：

  p-Hydroxyphenacyl photoremovable protecting groups — Robust photochemistry despite substituent diversity

  摘要：

  一项关于各种取代基对对羟基苯乙酯光化学重排影响的广泛研究表明，常见取代基（如 F、MeO、CN、CO2R、CONH2 和 CH3）对光-Favorskii 重排和酸离去基团释放的速率和量子效率影响很小，对反应三重态的寿命影响也很小。当光解在缓冲水介质中进行时，pH 值超过发色团的基态 pKao（其中共轭碱是主要形式），则释放和重排的量子产率在所有取代基中都会降低。否则，取代基对这些坚固发色团的光反应影响很小。

  DOI：

  10.1139/v10-143

文献信息

• Mechanism and Mechanism-Based Inactivation of 4-Hydroxyphenylpyruvate Dioxygenase
  作者：B.J.R. Forbes、G.A. Gordon

  DOI：10.1006/bioo.1994.1028

  日期：1994.12

  Six substrate analogs of 4-hydroxyphenylpyruvate, specifically pentafluorophenylpyruvate, 4-hydroxytetrafluorophenylpyruvate,2-thienylpyruvate, 3-thienylpyruvate, thiophenol oxalate, and p-thiocresoloxalate were synthesized and their interactions with porcine liver 4-hydroxyphenylpyruvate dioxygenase investigated. Both pentafluorophenylpyruvate and thiophenol oxalate are competitive inhibitors of the enzyme with Ki values of 14 and 150 mu M, respectively, but p-thiocresol oxalate has no effect on the enzymic activity. The other three substrate analogs are both substrates and mechanism-based inactivators of the enzyme with the following kinetic characteristics (compound, K-m, V-max, k(mact), K', partition ratio) at pH 6.0, 37 degrees C, and an air atmosphere: 4-hydroxytetrafluorophenylpyruvate, 50 mu M, 1.9 mkat/ kg, 1.5/min, 70 mu M 4.2; 2-thienylpyruvate, 500 mu M, 7.8 mkat/kg, 0.6/min, 400 CLM, 41; 3thienylpymvate, 250 mu M, 2 9 mkatikg, 0.6/min, 300 CLM, 22. When inactivated, the dioxygenase was found to contain per mole of active enzyme, 0.78 mol of label from 3-thienyt3 [3H]pyruvate and 0.85 mol of label from 4-hydroxytetrafluorophenyl-3 [3H]pyruvate. The product formed from the enzyme-catalyzed oxidation of 3-thienylpyruvate was determined to be 3-carboxymethyl-3-thiolene-2-one. The implication of these results to the mechanism of the dioxygenase is considered, (C) 1994 Academic Press, Inc.
• Partially fluorinated heterocyclic compounds part vii. New syntheses of 4,5,6,7-tretrafluoro-2-methylbenzo[b]furan
  作者：G.M. Brooke

  DOI：10.1016/s0040-4039(00)89737-3

  日期：1968.1