(E)-ethyl 3-(2-(methylcarbamoyl)phenyl)acrylate | 1355020-58-4

• 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-(methylcarbamoyl)phenyl)acrylate
• 英文别名: ethyl (E)-3-(2-(methylcarbamoyl)phenyl)acrylate；ethyl (E)-3-[2-(methylcarbamoyl)phenyl]prop-2-enoate
• CAS: 1355020-58-4
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: UVDOLPVFOLLCHX-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 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：
  3

反应信息

• 作为产物：
  描述：

  苯甲酰氯 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 三乙胺 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 7.0h， 生成 (E)-ethyl 3-(2-(methylcarbamoyl)phenyl)acrylate
  参考文献：
  名称：

  Complete Switch of Selectivity in the C–H Alkenylation and Hydroarylation Catalyzed by Iridium: The Role of Directing Groups

  摘要：

  A complete switch in the Cp*Ir(III)-catalyzed paths between C-H olefination and hydroarylation was found to be crucially dependent on the type of directing groups. This dichotomy in product distribution was correlated to the efficiency in attaining syn-coplanarity of olefin-inserted 7-membered iridacycles. Theoretical studies support our hypothesis that the degree of flexibility of this key intermediate modulates the beta-H elimination, which ultimately affords the observed chemoselectivity.

  DOI：

  10.1021/jacs.5b09824

文献信息

• Cp∗Co(III)-catalyzed oxidative C–H alkenylation of benzamides with ethyl acrylate
  作者：Yudai Suzuki、Bo Sun、Tatsuhiko Yoshino、Motomu Kanai、Shigeki Matsunaga

  DOI：10.1016/j.tet.2015.02.032

  日期：2015.7

  The utility of Cp∗Co(III)-catalysts was expanded to oxidative C–C bond-forming reaction. In situ-generated Cp∗Co(III)-catalyst, rather than a preformed cationic Cp∗Co(III)-complex, was effective. Oxidative alkenylation of benzamides and acetanilide with ethyl acrylate proceeded with silver acetate as a stoichiometric oxidant, giving products in up to 93% yield.

  Cp ＊ Co（III）催化剂的用途扩展到了氧化性C–C键形成反应。在原位生成的Cp ＊ Co（III）催化剂比预先形成的阳离子Cp ＊ Co（III）络合物有效。苯甲酰胺和乙酰苯胺与丙烯酸乙酯的氧化烯基化反应以乙酸银作为化学计量的氧化剂进行，产率高达93％。
• Urea‐Substituted Tetramethylcyclopentadienyl Ligands for Supramolecularly Accelerated Rh ^III ‐Catalyzed <i>ortho</i> ‐C−H Olefination of Benzoic Acid Derivatives
  作者：David Maurer、Bernhard Breit

  DOI：10.1002/chem.202005130

  日期：2021.2.5

  Through kinetic studies and NMR titration experiments, the catalysts’ substrate recognition ability mediated by hydrogen bonding was identified to be the reason for this effect. Introduction of pyridone‐phosphine ligands capable of forming additional H‐bond interactions increased the catalytic performance even further. By unveiling a proportionality between reaction rate and relative complex formation

  空气稳定且易于结晶的Rh III的设计与合成据报道，用脲部分取代的环戊二烯基催化剂能够促进苯甲酸衍生物的CHH烯化反应。通过动力学研究和NMR滴定实验，确定了氢键介导的催化剂底物识别能力是造成这种效应的原因。能够形成额外的H键相互作用的吡啶酮-膦配体的引入进一步提高了催化性能。通过揭示反应速率和相对复杂的形成焓之间的比例关系，支持了超分子催化剂预形成的假设。它在多种基材上的应用证明了催化剂体系的优势，与广泛使用[RhCp * Cl 2 ]的结果相比，通常可以提高收率。2。
• Palladium-catalyzed C–H Alkenylation of <i>C</i>-Aryl Nitrones
  作者：Megumi Hasegawa、Arisa Nomoto、Takuya Suga、Takahiro Soeta、Yutaka Ukaji

  DOI：10.1246/cl.160821

  日期：2017.1.5

  Palladium-catalyzed C–H alkenylation of C-aryl N-t-butyl nitrones with ethyl acrylate produced ortho-alkenylated benzamide derivatives via isomerization of the nitrone moiety. The use of 1,1,1,3,3,3-hexafluoro-2-propanol/acetic acid as a solvent resulted in effective C–H alkenylation, while competitive 1,3-dipolar cycloaddition was completely suppressed.

  钯催化的 C-芳基 N-叔丁基硝酮与丙烯酸乙酯的 C-H 烯基化通过硝酮部分的异构化产生邻烯基化的苯甲酰胺衍生物。使用 1,1,1,3,3,3-六氟-2-丙醇/乙酸作为溶剂导致有效的 C-H 烯基化，同时完全抑制了竞争性 1,3-偶极环加成。
• 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.