ethyl (E)-2-fluoro-p-hydroxycinnamate | 150780-77-1

• 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: ethyl (E)-2-fluoro-p-hydroxycinnamate
• 英文别名: 2-Propenoic acid, 2-fluoro-3-(4-hydroxyphenyl)-, ethyl ester, (E)-；ethyl (E)-2-fluoro-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 150780-77-1
• 化学式: C₁₁H₁₁FO₃
• 分子量: 210.205
• InChiKey: XRTWVMMMFVPKCF-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-fluoro-p-hydroxycinnamate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以72%的产率得到(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
• 作为产物：
  描述：

  2-氟-2-磷酰基乙酸三乙酯 、 4-三甲基硅氧苯甲醛 在 正丁基锂 作用下， 生成 ethyl (E)-2-fluoro-p-hydroxycinnamate
  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

文献信息

• Microwave-Assisted One-Pot Synthesis of α-Fluoro-α,β-Unsaturated Esters under Solvent-Free Conditions
  作者：Xiaochun Yu、Aishan Ren、Xiongjun Yang、Jing Hong

  DOI：10.1055/s-2008-1078213

  日期：——

  A microwave-assisted approach for the synthesis of α-fluoro-α,β-unsaturated esters from ethyl bromofluoroacetate, aldehydes, and triphenylphosphine in the presence of Zn-Cu under solvent-free conditions was achieved. The reaction was accomplished within five minutes with good product yields.

  实现了在无溶剂条件下，在 Zn-Cu 存在下，从溴氟乙酸乙酯、醛和三苯基膦合成 α-氟-α,β-不饱和酯的微波辅助方法。反应在五分钟内完成，产物收率良好。