4-(4-fluorophenyl)-2-(4-methoxyphenyl)quinoline | 1447235-55-3

• 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: 4-(4-fluorophenyl)-2-(4-methoxyphenyl)quinoline
• 英文别名: 4-(4-Fluorophenyl)-2-(4-methoxyphenyl)quinoline
• CAS: 1447235-55-3
• 化学式: C₂₂H₁₆FNO
• 分子量: 329.374
• InChiKey: DJFRMWKVKJZYOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2E)-3-(4-氟苯基)-1-(4-甲氧基苯基)丙-2-烯-1-酮 在 四氯化钛 、 三乙胺 、 sodium hydroxide 、 亚硝酸异戊酯 、 三氯乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 4-(4-fluorophenyl)-2-(4-methoxyphenyl)quinoline
  参考文献：
  名称：

  Synthesis of Quinolines from N-Tosyl-1-azadienes

  摘要：

  A route to aryl-substituted quinolines from N-tosyl 1-azadienes is described. The key steps are a [4+2] cycloaddition with benzyne followed by base treatment of the 1,4-dihydroquinoline product. The N-tosyl 1-azadienes were prepared from readily accessible cinnamaldehyde and chalcone substrates by condensation with p-TsNH2. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.726388

文献信息

• TMSBr-Promoted Cascade Cyclization of ortho-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications
  作者：Fengyan Jin、Tao Yang、Xian-Rong Song、Jiang Bai、Ruchun Yang、Haixin Ding、Qiang Xiao

  DOI：10.3390/molecules24213999

  日期：——

  Difficult-to-access 4-bromo quinolines are constructed directly from easily prepared ortho-propynol phenyl azides using TMSBr as acid-promoter. The cascade transformation performs smoothly to generate desired products in moderate to excellent yields with good functional groups compatibility. Notably, TMSBr not only acted as an acid-promoter to initiate the reaction, and also as a nucleophile. In addition

  使用 TMSBr 作为酸促进剂，从容易制备的邻丙炔苯基叠氮化物直接构建难以获得的 4-溴喹啉。级联转化顺利进行，以中等至优异的产率生成所需的产物，并具有良好的官能团兼容性。值得注意的是，TMSBr 不仅充当酸促进剂以引发反应，而且还充当亲核试剂。此外，作为关键中间体的4-溴喹啉可以进一步进行偶联反应或亲核反应，以提供多种在喹啉C4位具有分子多样性的官能化化合物。
• 2,4-Diarylquinolines: Synthesis, Absorption and Emission Properties
  作者：Adewale O. Adeloye、Malose J. Mphahlele

  DOI：10.3184/174751914x13945617338344

  日期：2014.4

  The absorption and emission spectra of series of 2,4-diarylquinolines prepared via palladium catalysed Suzuki-Miyaura cross-coupling of 2-aryl-4-chloroquinolines with arylboronic acids were measured in solution to understand the influence of substituents on intramolecular charge transfer.

  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。
• Synthesis of Quinolines from <i>N</i>-Tosyl-1-azadienes
  作者：Sean Stokes、Keith T. Mead

  DOI：10.1080/00397911.2012.726388

  日期：2013.10.2

  A route to aryl-substituted quinolines from N-tosyl 1-azadienes is described. The key steps are a [4+2] cycloaddition with benzyne followed by base treatment of the 1,4-dihydroquinoline product. The N-tosyl 1-azadienes were prepared from readily accessible cinnamaldehyde and chalcone substrates by condensation with p-TsNH2. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.