methyl 2-fluoro-6-[(E)-styryl]benzoate | 1286261-41-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 2-fluoro-6-[(E)-styryl]benzoate
• 英文别名: (E)-methyl 2-fluoro-6-styrylbenzoate；methyl 2-fluoro-6-[(E)-2-phenylethenyl]benzoate
• CAS: 1286261-41-3
• 化学式: C₁₆H₁₃FO₂
• 分子量: 256.276
• InChiKey: CKRVBBGGYKXRPS-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻氟苯甲酸 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 methyl 2-fluoro-6-[(E)-styryl]benzoate
  参考文献：
  名称：

  Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group

  摘要：

  The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. alpha,beta-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the beta-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.

  DOI：

  10.1021/jo200509m

文献信息

• Ru-Catalyzed (<i>E</i>)-Specific <i>ortho</i>-C–H Alkenylation of Arenecarboxylic Acids by Coupling with Alkenyl Bromides
  作者：Zhiyong Hu、Florian Belitz、Guodong Zhang、Florian Papp、Lukas J. Gooßen

  DOI：10.1021/acs.orglett.1c00956

  日期：2021.5.7

  alkenyl bromides, (E)-configured vinyl arenes or dienes are formed exclusively. Mechanistic studies show that this selectivity is achieved because the (E)-configured alkenyl bromides undergo a smooth coupling, whereas the (Z)-isomers are rapidly eliminated with the formation of alkynes.

  在[对-异丙基）RuCl 2 ] 2的存在下，（E）-构型的烯基溴化物与芳族羧酸盐偶合形成邻-乙烯基苯甲酸。这种C–H乙烯基化无需任何活化的膦配体就可以高产率进行，并且具有出色的官能团耐受性。从烯基溴化物的常见（E / Z）混合物开始，仅形成（E）构型的乙烯基芳烃或二烯。机理研究表明，实现这种选择性的原因是，（E）-构型的烯基溴化物经历了平滑的偶联，而（Z异构体会随着炔烃的形成而迅速消除。
• Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group
  作者：Satoshi Mochida、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo200509m

  日期：2011.5.6

  The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. alpha,beta-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the beta-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.