2-(4-chlorophenyl)-4-(4-methoxyphenyl)quinoline | 678973-61-0

• 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: 2-(4-chlorophenyl)-4-(4-methoxyphenyl)quinoline
• CAS: 678973-61-0
• 化学式: C₂₂H₁₆ClNO
• 分子量: 345.828
• InChiKey: FYQPSAMRXGZTRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-chloro-2-(4-chloro)phenyl quinoline 、 4-甲氧基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 、 三环己基膦 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以61%的产率得到2-(4-chlorophenyl)-4-(4-methoxyphenyl)quinoline
  参考文献：
  名称：

  2,4-Diarylquinolines: Synthesis, Absorption and Emission Properties

  摘要：

  为了了解取代基对分子内电荷转移的影响，我们在溶液中测量了钯催化 2-芳基-4-氯喹啉与芳基硼酸的 Suzuki-Miyaura 交叉偶联反应制备的一系列 2,4-二芳基喹啉的吸收和发射光谱。

  DOI：

  10.3184/174751914x13945617338344

文献信息

• Mechanistic Insights into the B(C₆F₅)₃-Initiated Aldehyde–Aniline–Alkyne Reaction To Form Substituted Quinolines
  作者：Valerio Fasano、James E. Radcliffe、Michael J. Ingleson

  DOI：10.1021/acs.organomet.7b00174

  日期：2017.4.24

  A substoichiometric quantity of the Lewis acid B(C6F5)(3) is sufficient to initiate the aldehyde-amine-alkyne reaction, in a one-pot methodology that enables the synthesis of a range of functionalized quinolines. Optimization studies revealed that key requirements for the high-yielding tricomponent reaction initiated by B(C6F5)(3) at raised temperatures include an excess of the in situ generated imine (which acts as a hydrogen acceptor) and an alkyne substituent able to stabilize positive charge buildup during the cyclization. Mechanistic experiments revealed that under these conditions B(C6F5)(3) is acting as a Lewis acid-assisted Bronsted acid; with H2O-B(C6F5)(3) being the key species enabling catalytic quinoline formation. This was indicated by deuterium labeling studies and the observation that the cyclization of N-(3-phenylpropargyl)aniline using B(C6F5)(3) under anhydrous conditions afforded the zwitterion [N-H-3-B(C6F5)(3)-4-Ph-quinolinium], which does not undergo protodeboronation to release B(C6F5)(3) and the quinoline product under a range of conditions. Finally, a brief substrate scope exploration demonstrated that this is an operationally Simple and effective methodology for the production of functionalized quinolines.