(E)-2-fluoro-p-hydroxycinnamic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-fluoro-p-hydroxycinnamic acid
• 英文别名: (E)-2-fluoro-3-(4-hydroxyphenyl)prop-2-enoic acid
• 化学式: C₉H₇FO₃
• 分子量: 182.151
• InChiKey: SBIZDOWXYPNTOJ-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-三甲基硅氧苯甲醛 在 sodium hydroxide 、 正丁基锂 作用下， 以 甲醇 为溶剂， 反应 20.5h， 生成 (E)-2-fluoro-p-hydroxycinnamic acid
  参考文献：
  名称：

  Mechanistic and stereochemical study of phenylpyruvate tautomerase

  摘要：

  A variety of substrates and potential enol/enolate mimics for the product/transition state of the enzyme phenylpyruvate tautomerase (E.C. 5.3.2.1) have been prepared and studied. Their stereostructures have been secured by a combination of NMR spectroscopy based on vicinal H-F and H-C coupling constants and X-ray crystallography. On the basis of the inhibition by stereoisomeric substituted cinnamates, it has been concluded that the enzyme produces the thermodynamically less stable (E) enol via a syn tautomerization transition state. Free energy profiles for the reaction suggest that vinyl fluorides act as product analogues. Because amide and dicarboxylate enolate mimics are relatively poor inhibitors of the enzyme, it is believed that an enolate is not involved in the tautomerization process.

  DOI：

  10.1021/ja00069a006