methyl (E)-3-(2-acetylamino-5-methylphenyl)propenoate

• 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: methyl (E)-3-(2-acetylamino-5-methylphenyl)propenoate
• 英文别名: methyl (E)-3-(2-acetamido-5-methylphenyl)acrylate；(E)-methyl 3-(2-acetamido-5-methylphenyl)acrylate；methyl (E)-3-(2-acetamido-5-methylphenyl)prop-2-enoate
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: OAEDZVPGFMOGHD-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙烷,三氯氟- 在 dipotassium peroxodisulfate 、 palladium diacetate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl (E)-3-(2-acetylamino-5-methylphenyl)propenoate
  参考文献：
  名称：

  高效Pd催化乙酰苯胺的邻位烯烃化：广泛的底物范围和高耐受性

  摘要：

  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。

  DOI：

  10.1002/asia.201000613

文献信息

• 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。
• Rhodium(III)-catalyzed internal oxidative coupling of N-hydroxyanilides with alkenes via C–H activation
  作者：Jing Wen、An Wu、Pei Chen、Jin Zhu

  DOI：10.1016/j.tetlet.2015.07.070

  日期：2015.9

  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.
• Catalytic Coupling of Haloolefins with Anilides
  作者：Vladimir G. Zaitsev、Olafs Daugulis

  DOI：10.1021/ja050366h

  日期：2005.3.1

  A strategy in which C-H activation reactions promoted by Pd(II) have been combined with beta-heteroatom elimination to create a catalytic cycle achieving the arylation of haloacrylates is reported. The catalytic cycle can be subdivided into four parts: (1) C-H activation; (2) the functionalization step, migratory insertion of the olefin into a metal-carbon bond; (3) beta-heteroatom elimination; and (4) exchange of metal halide (if X = halogen) for a less coordinating anion. In this catalytic cycle, the oxidation state of the metal does not change, and an oxidant is not required. The method is more functional group tolerant compared with the existing alkene-arene coupling methods based on electrophilic C-H activation.
• 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。