(E)-ethyl 3-(2-acetamido-5-fluorophenyl)acrylate | 1355020-49-3

• 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: (E)-ethyl 3-(2-acetamido-5-fluorophenyl)acrylate
• 英文别名: ethyl (E)-3-(2-acetamido-5-fluorophenyl)prop-2-enoate
• CAS: 1355020-49-3
• 化学式: C₁₃H₁₄FNO₃
• 分子量: 251.257
• InChiKey: WHDLQUZRRLVPII-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氟乙酰苯胺 、 丙烯酸乙酯 在 六氟磷酸钾 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 copper(II) acetate monohydrate 作用下， 以 水 为溶剂， 反应 20.0h， 以74%的产率得到(E)-ethyl 3-(2-acetamido-5-fluorophenyl)acrylate
  参考文献：
  名称：

  Ruthenium-Catalyzed Oxidative C–H Alkenylations of Anilides and Benzamides in Water

  摘要：

  A cationic ruthenium(II) complex enabled efficient oxidative alkenylations of anilides in water as a green solvent and proved applicable to double C-H bond functionalizations of (hetero)aromatic amides with ample scope. Detailed studies provided strong support for a change of ruthenation mechanism in the two transformations, with an irreversible metalation as the key step in cross-dehydrogenative alkenylations of benzamides.

  DOI：

  10.1021/ol203251s

文献信息

• A 2-acylamino-5-halogenated-cinnamic acid derivative and method for its production
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：EP0376103A1

  公开（公告）日：1990-07-04

  A 2-acylamino-5-halogenated-cinnamic acid derivative represented by the formula (III) which is useful as an intermediate for producing medicines and agricultural chemicals: wherein Ac represents a lower acyl group, R represents a hydrogen atom or a lower alkyl group, and X₁ represents a halogen atom. This derivative is obtained by reacting a compound represented by the formula (I), wherein Ac and X₁ are as defined above, and X₂ represents a bromine or iodine atom, with acrylic acid or its ester represented by the formula (II), CH₂=CHCOOR      (II) where R is as defined above, in the presence of a palladium catalyst, a tri(un­substituted- or substituted-phenyl)phosphine and an acid-binding agent.

  一种由式 (III) 表示的 2-酰氨基-5-卤代肉桂酸衍生物，可用作生产药物和农用化学品的中间体： 其中 Ac 代表低级酰基，R 代表氢原子或低级烷基，X₁ 代表卤素原子。这种衍生物是由式 (I) 所代表的化合物反应得到的、 其中 Ac 和 X₁ 如上定义，X₂ 代表溴原子或碘原子、 与式 (II) 所代表的丙烯酸或其酯、 CH₂=CHCOOR (II) 其中 R 如上定义、 在钯催化剂、三（未取代或取代苯基）膦和酸结合剂的存在下。
• US4997972A
  申请人：——

  公开号：US4997972A

  公开（公告）日：1991-03-05
• Ruthenium-Catalyzed Oxidative C–H Alkenylations of Anilides and Benzamides in Water
  作者：Lutz Ackermann、Lianhui Wang、Ratnakancana Wolfram、Alexander V. Lygin

  DOI：10.1021/ol203251s

  日期：2012.2.3

  A cationic ruthenium(II) complex enabled efficient oxidative alkenylations of anilides in water as a green solvent and proved applicable to double C-H bond functionalizations of (hetero)aromatic amides with ample scope. Detailed studies provided strong support for a change of ruthenation mechanism in the two transformations, with an irreversible metalation as the key step in cross-dehydrogenative alkenylations of benzamides.