α-fluoro-p-coumaric acid | 18238-96-5

• 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: α-fluoro-p-coumaric acid
• 英文别名: 4-Hydroxy-α-fluor-zimtsaeure；2-fluoro-3-(4-hydroxyphenyl)prop-2-enoic Acid
• CAS: 18238-96-5
• 化学式: C₉H₇FO₃
• 分子量: 182.151
• InChiKey: SBIZDOWXYPNTOJ-UHFFFAOYSA-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-乙酰氧基苯甲醛 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 α-fluoro-p-coumaric acid
  参考文献：
  名称：

  有机氟化合物。第XL部分。氟草酰乙酸二乙酯与醛的进一步反应

  摘要：

  研究了由脂族和芳族醛与氟乙二氧乙酸二乙酯合成α-氟不饱和酸的范围。酮和酯的α-甲酰基衍生物以醛形式反应。2-氟-3-（2-噻吩基）丙烯酸可能被硝化，可能在噻吩环的5位。2-氟-3-（1-萘基）丙烯酸环化成2-氟-4,5-苯并茚-1-酮（VIII）。

  DOI：

  10.1039/j39680001232

文献信息

• Analogue Chromophore Study of the Influence of Electronic Perturbation on Color Regulation of Photoactive Yellow Protein†
  作者：Hiroshi Yamada、Masato Kumauchi、Norio Hamada、Xiang-Guo Zheng、Il Ho Park、Katsuyoshi Masuda、Kazuo Yoshihara、Fumio Tokunaga

  DOI：10.1562/2006-01-17-ra-781

  日期：——

  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.
• Organic fluorine compounds. Part XL. Further reactions of diethyl fluoro-oxaloacetate with aldehydes
  作者：Ernst D. Bergmann、Israel Shahak、Etan Sal'i、Zeev Aizenshtat

  DOI：10.1039/j39680001232

  日期：——

  The scope of the synthesis of α-fluoro-unsaturated acids from aliphatic and aromatic aldehydes and diethyl fluoro-oxaloacetate has been studied. α-Formyl derivatives of ketones and esters react in their aldehydic forms. 2-Fluoro-3-(2-thienyl)acrylic acid could be nitrated, probably in the 5-position of the thiophen ring. 2-Fluoro-3-(1-naphthyl)acrylic acid cyclized to 2-fluoro-4,5-benzinden-1-one (VIII)

  研究了由脂族和芳族醛与氟乙二氧乙酸二乙酯合成α-氟不饱和酸的范围。酮和酯的α-甲酰基衍生物以醛形式反应。2-氟-3-（2-噻吩基）丙烯酸可能被硝化，可能在噻吩环的5位。2-氟-3-（1-萘基）丙烯酸环化成2-氟-4,5-苯并茚-1-酮（VIII）。