Ethyl 2-fluoro-3-(4-hydroxyphenyl)prop-2-enoate | 930106-43-7

• 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 2-fluoro-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 930106-43-7
• 化学式: C₁₁H₁₁FO₃
• 分子量: 210.205
• InChiKey: XRTWVMMMFVPKCF-UHFFFAOYSA-N

物化性质

• 沸点：
  323.604±32.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.232±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 2-fluoro-3-(4-hydroxyphenyl)prop-2-enoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 α-fluoro-p-coumaric acid
  参考文献：
  名称：

  Analogue Chromophore Study of the Influence of Electronic Perturbation on Color Regulation of Photoactive Yellow Protein†

  摘要：

  We report a unique lambda(max) shift of the absorption maximum of a photoactive yellow protein (PYP) analogue reconstituted with a fluorinated chromophore (F-PYP). The difference in lambda(max), between the free chromophore and the protein was significantly larger than that with the native chromophore. We concluded that the unusual,lambda(max) shift is caused by the electronegative character of the fluorine atom and not by steric hindrance. This result suggests that formation of a hydrogen bond between the fluorine atom and one or more amino acid residues could neutralize its electron-withdrawing character. The properties of analogues of PYP with brominated and methylated chromophore could be explained as an effect of steric hindrance.

  DOI：

  10.1562/2006-01-17-ra-781
• 作为产物：
  描述：

  ethyl 3-(4-((tert-butyldimethylsilyl)oxy)phenyl)-2-fluoroacrylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 Ethyl 2-fluoro-3-(4-hydroxyphenyl)prop-2-enoate
  参考文献：
  名称：

  Analogue Chromophore Study of the Influence of Electronic Perturbation on Color Regulation of Photoactive Yellow Protein†

  摘要：

  We report a unique lambda(max) shift of the absorption maximum of a photoactive yellow protein (PYP) analogue reconstituted with a fluorinated chromophore (F-PYP). The difference in lambda(max), between the free chromophore and the protein was significantly larger than that with the native chromophore. We concluded that the unusual,lambda(max) shift is caused by the electronegative character of the fluorine atom and not by steric hindrance. This result suggests that formation of a hydrogen bond between the fluorine atom and one or more amino acid residues could neutralize its electron-withdrawing character. The properties of analogues of PYP with brominated and methylated chromophore could be explained as an effect of steric hindrance.

  DOI：

  10.1562/2006-01-17-ra-781