(E)-methyl 3-acetylcinnamate | 1313813-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-methyl 3-acetylcinnamate
• 英文别名: methyl (E)-3-(3-acetylphenyl)prop-2-enoate
• CAS: 1313813-62-5
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: BXOOOHQIGMESQD-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-acetylcinnamate 、 C.I.酸性橙108 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以92%的产率得到(E)-N-(2-hydroxyethyl)-3-acetylcinnamamide
  参考文献：
  名称：

  Sodium carbonate mediated regioselective synthesis of novel N-(hydroxyalkyl)cinnamamides

  摘要：

  A synthetic protocol for the direct synthesis of N-(hydroxyalkyl)cinnamamides from cinnamates and aminoalcohols in the presence of sodium carbonate as the base is presented. A wide variety of N-(hydroxyallcyl)cinnamamides were isolated in up to 99% yields. The reaction is highly regioselective and yields only N-acylated products by 1,2-addition of aminoalcohols to cinnamates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.086
• 作为产物：
  描述：

  3'-溴苯乙酮 、 丙烯酸甲酯（MA） 在 [Pd{C₆H₂-(CH₂CH₂NH₂)-(OMe)2-3,4}Br(PPh₃)] 、 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.83h， 以87%的产率得到(E)-methyl 3-acetylcinnamate
  参考文献：
  名称：

  含磷-氮混合供体的单体原钯配合物在Heck反应中的应用

  摘要：

  合成了高藜芦胺和三苯基膦的[Pd {C 6 H 2（CH 2 CH 2 NH 2）-（OMe）2，3,4 } Br（PPh 3）]原钯原酸酯复合物，并研究了其在Heck偶联反应中的应用。对于芳基碘，溴化物甚至氯化物以及芳烃磺酰氯的Heck反应，已证明该络合物比相应的二聚催化剂更具活性。使用催化量的[Pd {C 6 H 2（CH 2 CH 2 NH 2）-（OMe）2，3,4} Br（PPh 3）]在130°C下于NMP中为热稳定且对氧不敏感的络合物。

  DOI：

  10.1016/j.tetlet.2011.07.036

文献信息

• Pd0.09Ce0.91O2-δ: A sustainable ionic solid-solution precatalyst for heterogeneous, ligand free Heck coupling reactions
  作者：Philani P. Mpungose、Neo I. Sehloko、Venkata D.B.C. Dasireddy、Narayanappa Mahadevaiah、Glenn E. Maguire、Holger B. Friedrich

  DOI：10.1016/j.mcat.2017.09.022

  日期：2017.12

  incorporated into the lattice structure of ceria. The effect of the reaction conditions on the catalytic properties of the Pd0.09Ce0.91O2-δ solid solution catalyst initially was studied in detail with the model Heck reaction of iodobenzene and methylacrylate to obtain optimum reaction conditions. The Pd0.09Ce0.91O2-δ solid solution catalyst then afforded substituted alkenes in good to excellent yields

  描述了一种制备二氧化铈中取代的Pd 2+金属离子的快速简便的方法，即Pd 0.09 Ce 0.91 O2 -δ固溶体氧化物。通过XRD，ICP-OES，BET，XPS，SEM，EDX，TEM，TGA和拉曼光谱对Pd 0.09 Ce 0.91 O2 -δ固溶体氧化物进行了全面表征。所有表征技术都强烈建议将Pd 2+成功地掺入二氧化铈的晶格结构中。反应条件对Pd 0.09 Ce 0.91 O2 -δ催化性能的影响首先用碘代苯和丙烯酸甲酯的Heck模型反应对固溶催化剂进行了详细研究，以获得最佳反应条件。然后，在这些最佳反应条件下，Pd 0.09 Ce 0.91 O2 -δ固溶体催化剂以良好或优异的收率提供了取代的烯烃。还研究了立体效应和电子效应，发现它们影响催化活性。所述用过的催化剂的表征表明，钯2+中的Pd 0.09铈0.91 ö 2-δ减小原位与Pd 0当用于Heck交叉偶联反应时。催化剂可
• Application of dimeric cyclopalladated complex of tribenzylamine as an efficient catalyst in the Heck cross-coupling reaction
  作者：Abdol R. Hajipour、Fatemeh Rafiee

  DOI：10.1016/j.jorganchem.2011.03.023

  日期：2011.7

  )} (μ-Br)]2 complex was investigated in the Heck–Mizoroki C–C cross-coupling reaction. This complex is an active and efficient catalyst for the Heck reaction of aryl iodides, bromides and even chlorides and also arenesulfonyl chlorides. The cross-coupled products were produced in excellent yields in short reaction time using a catalytic amount of [PdC6H4(CH2N(CH2Ph)2) (μ-Br)]2 complex in NMP at 130 °C

  在Heck – Mizoroki C – C交叉偶联反应中研究了[Pd C 6 H 4（CH 2 N（CH 2 Ph）2）}（μ-Br）] 2络合物的活性。该络合物是用于芳基碘化物，溴化物甚至氯化物以及芳烃磺酰氯的Heck反应的活性和有效催化剂。在130°C的NMP中使用催化量的[Pd C 6 H 4（CH 2 N（CH 2 Ph）2）（μ-Br）] 2络合物），可以在短反应时间内以优异的产率生产交联产物。C。
• The [RPPh3]2[Pd2X6] as a Catalyst Precursor for the Heck Cross-Coupling Reaction by in situ Formation of Stabilized Pd(0) Nanoparticles
  作者：Abdol Hajipour、Ghobad Azizi

  DOI：10.1055/s-0032-1317963

  日期：——

  Pd(II) anionic, square planar complexes of the type [RPPh3](2)[Pd2X2Cl4], where X = Cl, Br, have been applied for the first time as a catalyst precursor for the Heck reaction carried out in DMF at 140 degrees C. The highest yield was obtained for the most reducible ones, [MePPh3](2)[Pd2Br2Cl4], in DMF in the presence of NaHCO3 as a base. It was found that during the reaction, phosphonium halide stabilized Pd(0) nanoparticles of about 10 nm, which have been formed in situ from the palladium(II) precursor and Pd(0) colloidal nanoparticles acts as the reservoir for Pd(II) species via activation of the metal surface through the oxidative addition of aryl halides.