Z-2-fluoro-3-(3-chlorophenyl)acrylic acid | 110915-40-7

• 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: Z-2-fluoro-3-(3-chlorophenyl)acrylic acid
• 英文别名: (2Z)-3-(3-Chlorophenyl)-2-fluoroprop-2-enoic acid；(Z)-3-(3-chlorophenyl)-2-fluoroprop-2-enoic acid
• CAS: 110915-40-7
• 化学式: C₉H₆ClFO₂
• 分子量: 200.597
• InChiKey: FIZXMBFEGMNOLU-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(3-Chloro-phenyl)-2-fluoro-3-hydroxy-propionic acid ethyl ester 在 sodium hydroxide 、 氯化亚砜 作用下， 生成 Z-2-fluoro-3-(3-chlorophenyl)acrylic acid 、 (Z)-3-(3-Chloro-phenyl)-2-fluoro-acrylic acid
  参考文献：
  名称：

  Elkik, Elias; Francesch, Charlette, Bulletin de la Societe Chimique de France, 1986, # 3, p. 423 - 428

  摘要：

  DOI：

文献信息

• Copper-Catalyzed Carboxylation of C–F Bonds with CO₂
  作者：Si-Shun Yan、Dong-Shan Wu、Jian-Heng Ye、Li Gong、Xin Zeng、Chuan-Kun Ran、Yong-Yuan Gui、Jing Li、Da-Gang Yu

  DOI：10.1021/acscatal.9b02351

  日期：2019.8.2

  An effective Cu-catalyzed selective formal carboxylation of C-F bonds with an atmospheric pressure of CO2 is reported. A variety of gem-difluoroalkenes, gem-difluorodienes, and alpha-trifluoro-methyl alkenes show high reactivity and selectivity for this ipso monocarboxylation. Under mild conditions, diverse important alpha-fluoroacrylic acids and alpha,alpha-difluorocarboxylates are obtained in good-to-high yields. Moreover, this operationally simple protocol features good functional group tolerance, is readily scalable, and the resulting products are readily converted into bioactive alpha-fluorinated carbonyl compounds, indicating potential application in biochemistry and drug discovery. Mechanistic studies reveal that fluorinated boronate esters might be vital intermediates in this transformation.