(E)-1-(3-chlorophenyl)-2-(3-quinolyl)ethene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (E)-1-(3-chlorophenyl)-2-(3-quinolyl)ethene
• 英文别名: 3-[(E)-2-(3-chlorophenyl)ethenyl]quinoline
• 化学式: C₁₇H₁₂ClN
• 分子量: 265.742
• InChiKey: UOSGKOMLFGQXSP-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-溴喹啉 、 1-氯-3-碘苯 、 乙烯三氟硼酸钾 在 potassium phosphate monohydrate 、 Pd/SiO₂ 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 28.0h， 以80%的产率得到(E)-1-(3-chlorophenyl)-2-(3-quinolyl)ethene
  参考文献：
  名称：

  One‐Pot Suzuki/Heck Sequence for the Synthesis of ( E )‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

  摘要：

  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.

  DOI：

  10.1002/adsc.201000028

文献信息

• 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.