(E)-methyl 3-(2-acetamido-5-fluorophenyl)acrylate | 1259100-53-2

• 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)-methyl 3-(2-acetamido-5-fluorophenyl)acrylate
• 英文别名: methyl (E)-3-(2-acetamido-5-fluorophenyl)acrylate；methyl (E)-3-(2-acetamido-5-fluorophenyl)prop-2-enoate
• CAS: 1259100-53-2
• 化学式: C₁₂H₁₂FNO₃
• 分子量: 237.231
• InChiKey: DFSLRGWYWOZAON-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  对氟硝基苯 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium acetate 、 氯化铵 、 锌 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 (E)-methyl 3-(2-acetamido-5-fluorophenyl)acrylate
  参考文献：
  名称：

  Rhodium(III)-catalyzed internal oxidative coupling of N-hydroxyanilides with alkenes via C–H activation

  摘要：

  Described herein is an efficient new method for ortho-olefination of anilides in the presence of AgSbF6 and NaOAc via rhodium(III)-catalyzed internal oxidative C-H bond activation based on hydroxyl as directing and oxidative group. A range of alkenes and functional groups on acetanilides is supported and a possible mechanism is proposed according to the experimental results. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.07.070

文献信息

• Highly Effective Pd-Catalyzed ortho Olefination of Acetanilides: Broad Substrate Scope and High Tolerability
  作者：Byung Seok Kim、Chungsik Jang、Dong Jin Lee、So Won Youn

  DOI：10.1002/asia.201000613

  日期：2010.11.2

  Bring it on! An effective Pd‐catalyzed ortho olefination of various acetanilides has been developed. This transformation has a broad substrate scope and wide functional‐group tolerability, regardless of the electronic and steric properties of acetanilide substrates, providing a straightforward access to highly functionalized arenes.

  来吧！已经开发出一种有效的Pd催化的各种乙酰苯胺的邻位烯烃化反应。不管乙酰苯胺底物的电子和位阻特性如何，这种转化都具有广泛的底物范围和宽泛的官能团耐受性，可直接进入高度官能化的芳烃。
• Non-coordinating-Anion-Directed Reversal of Activation Site: Selective C−H Bond Activation of<i>N</i>-Aryl Rings
  作者：Dawei Wang、Xiaoli Yu、Xiang Xu、Bingyang Ge、Xiaoli Wang、Yaxuan Zhang

  DOI：10.1002/chem.201600293

  日期：2016.6.13

  An Rh‐catalyzed selective C−H bond activation of diaryl‐substituted anilides is described. In an attempt to achieve C−H activation of C‐aryl rings, we unexpectedly obtained an N‐aryl ring product under non‐coordinating anion conditions, whereas the C‐aryl ring product was obtained in the absence of a non‐coordinating anion. This methodology has proved to be an excellent means of tuning and adjusting

  描述了二芳基取代的苯甲酰胺的Rh催化的选择性C H键活化。为了实现C-芳基环的CH活化，我们意外地在非配位阴离子条件下获得了N-芳基环产物，而C-芳基环的产物是在不存在非配位阴离子的条件下获得的。事实证明，该方法学是调节和调节C芳基和N选择性C H键活化的极佳方法芳基环。通过机械研究和理论计算使该方法合理化。另外，已经发现并证实，非配位阴离子明显提高了铑催化剂的催化活性，这为获得高化学选择性催化剂提供了有效的策略。机械实验也明确地排除了这种涉及银的转变中所谓的“银效应”的可能性。
• Pd(TFA)2-catalyzed oxidative coupling of anilides with olefins through CH bond activation under non-acidic conditions
  作者：Xiaoli Yu、Wei Yao、Huida Wan、Zhaojun Xu、Dawei Wang

  DOI：10.1016/j.jorganchem.2016.08.025

  日期：2016.11

  C-H bond activation is an important issue. The Pd-catalyzed and non-coordinating anion improved C-H bond activation was realized through the oxidative coupling reaction of anilides with olefins under non-acidic conditions. Additionally, the catalytic activity of palladium catalysts is enhanced by non-coordinating anions, further proving that non-coordinating anion can be used in palladium-involved reactions. (C) 2016 Elsevier B.V. All rights reserved.