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.
• Pd-Catalyzed Direct Cross-Coupling of Electron-Deficient Polyfluoroarenes with Heteroaromatic Tosylates
  作者：Shilu Fan、Jie Yang、Xingang Zhang

  DOI：10.1021/ol201706t

  日期：2011.8.19

  We report a Pd-catalyzed direct cross-coupling of electron-deficient polyfluoroarenes with heteroaromatic tosylates. The notable features of this reaction are its high reaction efficiency, excellent chemoselectivity, operational simplicity, and mild reaction conditions. We have applied this protocol to prepare the semiconducting materials in a highly efficient manner.

  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。