2-(perfluorophenyl)-4-phenylquinoline

• 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-(perfluorophenyl)-4-phenylquinoline
• 英文别名: 2-(2,3,4,5,6-Pentafluorophenyl)-4-phenylquinoline
• 化学式: C₂₁H₁₀F₅N
• 分子量: 371.309
• InChiKey: JAABHKHIMJLVKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• 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：
  6

反应信息

• 作为产物：
  描述：

  五氟苯 、 quinoline-2,4-diyl bis(tosylate) 在 potassium phosphate 、 1-金刚烷甲酸 、 palladium diacetate 、 2-(二环己基膦基)联苯 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 12.0h， 生成 2-(perfluorophenyl)-4-phenylquinoline
  参考文献：
  名称：

  Pd催化的电子缺陷型多氟芳烃与杂芳族甲苯磺酸盐的直接交叉偶联

  摘要：

  我们报告了P​​d催化的电子不足的多氟芳烃与杂芳族甲苯磺酸盐的直接交叉偶联。该反应的显着特征是其高反应效率，优异的化学选择性，操作简便和温和的反应条件。我们已应用此协议以高效的方式制备半导体材料。

  DOI：

  10.1021/ol201706t

文献信息

• Microwave promoted solvent-free one-pot three-component reaction to 2-pentafluorophenylquinoline derivatives
  作者：Jian-ming Zhang、Wen Yang、Li-ping Song、Xian Cai、Shi-zheng Zhu

  DOI：10.1016/j.tetlet.2004.04.179

  日期：2004.7

  A novel and efficient one-pot multi-component reaction of pentafluorobenzaldehyde, alkynes and anilines for the synthesis of 2-pentafluorophenyl substituted quinolines under microwave irradiation and a solvent-free condition is presented.

  提出了一种新颖高效的五氟苯甲醛，炔烃和苯胺的单锅多组分反应，该反应在微波和无溶剂条件下合成了2-五氟苯基取代的喹啉。
• 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.