6-chloro-2-(4-methylphenyl)-4-phenylquinoline | 21923-41-1

• 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: 6-chloro-2-(4-methylphenyl)-4-phenylquinoline
• 英文别名: 6-chloro-4-phenyl-2-(p-tolyl)quinoline
• CAS: 21923-41-1
• 化学式: C₂₂H₁₆ClN
• 分子量: 329.829
• InChiKey: JADCWKQUSAMNLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  氯化铱(III) 水合物 、 6-chloro-2-(4-methylphenyl)-4-phenylquinoline 以 乙二醇乙醚 为溶剂， 生成 [IrCl[chlorine-methyl substituted 2,4 diphenylquinoline]2]2
  参考文献：
  名称：

  Synthesis and photophysics of a new deep red soluble phosphorescent iridium(III) complex based on chlorine-methyl-substituted 2,4 diphenyl quinoline

  摘要：

  A new iridium complex with a chlorine-methyl-substituted 2,4 diphenyl quinoline, (Cl-MDPQ) ligand has been synthesized. The synthesized iridium metal complex, Ir(Cl-MDPQ)(2)(acac) where Cl-MDPQ=chlorinemethyl substituted, 2,4 diphenyl quinoline, acac=acetyl acetone is characterized by employing different techniques such as mass spectrometry, H-1 NMR, DTA/TGA, XRD, and FTIR. The molecular structures of Cl-MDPQ and Ir(Cl-MDPQ)(2)(acac) complexes are confirmed by the FTIR spectra. Strong singlet metal-to-ligand charge-transfer ((MLCT)-M-1) and triplet metal-to-ligand charge-transfer ((MLCT)-M-3) absorption peaks at 353 and 437 rim in tetrahydrofuran (THF) are reported in the synthesized complex, respectively. A deep red emitting Ir(Cl-MDPQ)(2)(acac) complex at 662 nm is promising for flexible organic devices. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jpcs.2011.09.011
• 作为产物：
  描述：

  1-(1-bromovinyl)-4-methylbenzene 在 碘 、 magnesium 、 cobalt(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 6-chloro-2-(4-methylphenyl)-4-phenylquinoline
  参考文献：
  名称：

  钴催化的邻氨基苯甲酸亲电胺化反应：制备缩合喹啉的捷径

  摘要：

  各种有机锌新戊酸酯与邻氨基苯甲酸酯的反应提供苯胺衍生物，其在酸性条件下环化提供缩合喹啉。使用烯基新戊酸锌、富电子芳基新戊酸锌或杂环新戊酸锌直接产生稠合喹啉，其中几种结构属于新的杂环支架。由于具有最佳的空穴能带排列和大的带隙，这些 N-杂环特别适用于有机发光二极管，因为它们具有高光致发光量子产率和长激子寿命，以及甲基铵碘化铅钙钛矿太阳能电池中的空穴传输材料.

  DOI：

  10.1021/jacs.8b11466

文献信息

• Green preparation of quinoline derivatives through FeCl₃·6H₂O catalyzed Friedlander reaction in ionic liquids
  作者：Jianji Wang、Xuesen Fan、Xinying Zhang、Lijun Han

  DOI：10.1139/v04-066

  日期：2004.7.1

  The preparation of substituted quinoline derivatives through a Friedlander condensation reaction utilizing the ionic liquid [bmim][BF₄] as the reaction medium and iron chloride hexahydrate (FeCl₃·6H₂O) as a catalyst is described. The advantages in using this method include its environmental friendliness, simple operating process in both mild and neutral reaction conditions, and good yields.Key words: ionic liquid, Friedlander reaction, quinoline derivatives, green chemistry.

  通过使用离子液体[bmim][BF₄]作为反应介质和六水合氯化铁（FeCl₃·6H₂O）作为催化剂，描述了通过Friedlander缩合反应制备取代喹啉衍生物的方法。使用这种方法的优点包括其环境友好性，在温和和中性反应条件下的简单操作过程以及良好的产率。关键词：离子液体，Friedlander反应，喹啉衍生物，绿色化学。
• A Novel Preparation of 4-Phenylquinoline Derivatives in Ionic Liquids
  作者：Xinying Zhang、Xuesen Fan、Jianji Wang、Yanzhen Li

  DOI：10.1002/jccs.200400194

  日期：2004.12

  A novel preparation of 4-phenylquinoline derivatives through acid-catalyzed Friedlander reaction in ionic liquid ([bmim][BF 4 ]) is described. The preparative procedure presented in this paper is operationally simple andenvironmentally benign. The reaction media and the catalyst used can be recovered and reused for at least four times without loss in the catalytic activity.

  介绍了一种在离子液体 ([bmim][BF 4 ]) 中通过酸催化弗里德兰德反应制备 4-苯基喹啉衍生物的新方法。本文介绍的制备程序操作简单且对环境无害。所用的反应介质和催化剂可以回收再利用至少四次而不会损失催化活性。
• Palladium-Catalyzed/Copper-Mediated Desulfurization and Aryl­­ation of Quinoline-2-(1H)-thione for Rapid Access to Quinoline Derivatives
  作者：Hai-Long Lu、Fu-Hu Guo、Tong-Lin Wang、Xi-Cun Wang、Zheng-Jun Quan

  DOI：10.1055/s-0039-1690765

  日期：2020.3

  An efficient method for carbon–carbon bond formation is described. The process employs the palladium-catalyzed and copper-mediated cross-coupling of quinoline-2-(1H)-thiones with arylboronic acids or alkynes through C–S bond cleavage without an inert atmosphere. The method provides rapid and general access to a diverse range of 2-substituted quinolines in a single step from a wide range of quinoline-2-(1H)-thiones

  描述了一种有效的碳-碳键形成方法。该方法采用钯催化和铜介导的喹啉-2-（1 H）-硫酮与芳基硼酸或炔烃通过CS键断裂的无惰性气氛的交叉偶联。该方法提供了从一个范围广泛的喹啉-2-（1 H）-硫酮和芳基硼酸或炔烃中快速而通用地通过一个步骤快速地获得范围广泛的2-取代喹啉的方法。
• PEG-SO3H as a catalyst in aqueous media: A simple, proficient and green approach for the synthesis of quinoline derivatives
  作者：M A NASSERI、S A ALAVI、B ZAKERINASAB

  DOI：10.1007/s12039-012-0353-y

  日期：2013.1

  A convenient and efficient method was developed for the synthesis of quinolines, an important class of potentially bioactive compounds. The quinoline derivatives were prepared in water, an excellent solvent in terms of environmental impact and with reduced waste production. PEG-SO3H effectively catalysed the one-pot synthesis of quinolines by the condensation of o-aminoaryl ketones and carbonyl compound with high yields (75–95%). The compounds were isolated by simple filtration in a high purity form.

  开发了一种便捷高效的方法用于合成喹啉类化合物，这是一类重要的具有潜在生物活性的化合物。喹啉衍生物在水中制备而成，水作为溶剂对环境影响极小且废料生成较少。PEG-SO3H 有效地催化了一锅煮合成喹啉的过程，通过邻氨基芳基酮和羰基化合物的缩合反应，产率高达 75-95%。这些化合物经过简单过滤便可获得高纯度形式。
• Sustainable Synthesis of Quinolines and Pyrimidines Catalyzed by Manganese PNP Pincer Complexes
  作者：Matthias Mastalir、Mathias Glatz、Ernst Pittenauer、Günter Allmaier、Karl Kirchner

  DOI：10.1021/jacs.6b10433

  日期：2016.12.7

  and pyrimidines using combinations of 2-aminobenzyl alcohols and alcohols as well as benzamidine and two different alcohols, respectively. These reactions proceed with high atom efficiency via a sequence of dehydrogenation and condensation steps that give rise to selective C-C and C-N bond formations, thereby releasing 2 equiv of hydrogen and water. A hydride Mn(I) PNP pincer complex recently developed

  本研究代表了第一个使用 2-氨基苄醇和醇以及苯甲脒和两种不同醇的组合来合成取代喹啉和嘧啶的环境友好、可持续和实用的例子。这些反应通过一系列脱氢和缩合步骤以高原子效率进行，产生选择性的 CC 和 CN 键形成，从而释放 2 当量的氢和水。我们实验室最近开发的氢化物 Mn(I) PNP 钳形复合物以非常有效的方式催化了这一过程。总共合成了 15 种不同的喹啉和 14 种不同的嘧啶，分离产率分别高达 91% 和 90%。

表征谱图