(E)-1-(4-acetylphenyl)-2-(3-quinolyl)ethene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-(4-acetylphenyl)-2-(3-quinolyl)ethene
• 英文别名: 1-[4-[(E)-2-quinolin-3-ylethenyl]phenyl]ethanone
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: NNZCHRLCLUSRCQ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴喹啉 、 1-(4-乙烯基-苯基)-乙酮 在 palladium diacetate 作用下， 以 水 为溶剂， 反应 6.0h， 以0.4381 g的产率得到(E)-1-(4-acetylphenyl)-2-(3-quinolyl)ethene
  参考文献：
  名称：

  Consecutive palladium-catalyzed Hiyama–Heck reactions in aqueous media under ligand-free conditions

  摘要：

  通过在水和空气条件下进行的一锅法Hiyama-Heck反应，从芳基溴合成对称和非对称（E）-1,2-二芳基乙烯。唯一所需的添加剂是氢氧化钠、乙酸钯和聚乙二醇，并且在许多情况下，产品可以通过简单地过滤水溶液来分离。

  DOI：

  10.1039/b707583a

文献信息

• Mechanistic Studies on the Pd-Catalyzed Vinylation of Aryl Halides with Vinylalkoxysilanes in Water: The Effect of the Solvent and NaOH Promoter
  作者：Alvaro Gordillo、Manuel A. Ortuño、Carmen López-Mardomingo、Agustí Lledós、Gregori Ujaque、Ernesto de Jesús

  DOI：10.1021/ja404255u

  日期：2013.9.18

  The mechanism of the Pd-catalyzed vinylation of aryl halides with vinylalkoxysilanes in water has been studied using different catalytic precursors. The NaOH promoter converts the initial vinylalkoxysilane into a highly reactive water-soluble vinylsilanolate species. Similarly, deuterium-labeling experiments have shown that, irrespective of the catalytic precursor used, vinylation occurs exclusively at the CH vinylic functionality via a Heck reaction and not at the C-Si bond via a Hiyama cross-coupling. The involvement of a Heck mechanism is interpreted in terms of the reduced nucleophilicity of the base in water, which disfavors the transmetalation step. The Heck product (beta-silylvinylarene) undergoes partial desilylation, with formation of a vinylarene, by three different routes: (a) hydrolytic desilylation by the aqueous solvent (only at high temperature); (b) transmetalation of the silyl olefin on the PdH Heck intermediate followed by reductive elimination of vinylarene; (c) reinsertion of the silyl olefin into the PdH bond of the Heck intermediate followed by beta-Si syn-elimination. Both the Hiyama and Heck catalytic cycles and desilylation mechanisms b and c have been computationally evaluated for the [Pd(en)Cl-2] precursor in water as solvent. The calculated Gibbs energy barriers support the reinsertion route proposed on the basis of the experimental results.
• One‐Pot Suzuki/Heck Sequence for the Synthesis of ( <i>E</i> )‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst <i>via</i> a Multi‐Component Reaction in 1,3‐Propanediol
  作者：Lionel Joucla、Giuseppe Cusati、Catherine Pinel、Laurent Djakovitch

  DOI：10.1002/adsc.201000028

  日期：2010.10.9

  AbstractThe synthesis of (E)‐stilbenes was performed following a one‐pot Suzuki/Heck sequence through the use of potassium vinyltrifluoroborate. The combination of heterogeneous palladium/silica (Pd/SiO2) catalyst with potassium phosphate monohydrate (K3PO4⋅H2O) as base resulted in useful to good isolated yields regardless of the ortho‐, meta‐ or para‐substitution of the aryl halides employed. In a sustainable approach, we found that bio‐sourced 1,3‐propanediol could advantageously replace N‐methylpyrrolidone (NMP) as similar yields were obtained. Moreover, the reactivity gap between aryl iodides and bromides resulting from the use of 1,3‐propanediol allowed an efficient multi‐component approach toward the synthesis of (E)‐stilbenes. Furthermore, this heterogeneous catalyst was found to be extremely robust despite the use of aerobic conditions and was successfully re‐used over several cycles.
• Consecutive palladium-catalyzed Hiyama–Heck reactions in aqueous media under ligand-free conditions
  作者：Álvaro Gordillo、Ernesto de Jesús、Carmen López-Mardomingo

  DOI：10.1039/b707583a

  日期：——

  Symmetric and asymmetric (E)-1,2-diarylethenes are synthesized from aryl bromides by consecutive one-pot Hiyama–Heck reactions carried out in water and under air; the only additives required are sodium hydroxide, palladium acetate and poly(ethylene glycol), and the products are isolable in many cases by simple filtration of the water solution.

  通过在水和空气条件下进行的一锅法Hiyama-Heck反应，从芳基溴合成对称和非对称（E）-1,2-二芳基乙烯。唯一所需的添加剂是氢氧化钠、乙酸钯和聚乙二醇，并且在许多情况下，产品可以通过简单地过滤水溶液来分离。