6-chloro-2-(4-nitrophenyl)-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: 6-chloro-2-(4-nitrophenyl)-4-phenylquinoline
• 化学式: C₂₁H₁₃ClN₂O₂
• mdl: MFCD00364553
• 分子量: 360.799
• InChiKey: XUFMGHDTMMZKPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 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：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-5-氯二苯甲酮 、 对硝基苯乙酮 在 aluminum hydrogen sulfate 作用下， 反应 24.0h， 以89%的产率得到6-chloro-2-(4-nitrophenyl)-4-phenylquinoline
  参考文献：
  名称：

  无溶剂条件下 M(HSO4)n (M=Al, Mg, Ca) 催化的 Friedländer 喹啉合成

  摘要：

  多取代的喹啉由 2-氨基二苯甲酮、乙酰乙酸乙酯或酮在金属硫酸氢盐 [M(HSO 4 ) n ] 存在下在 70 °C 无溶剂条件下以良好至高产率合成。

  DOI：

  10.3987/com-08-11442

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。
• Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones
  作者：Cheng-Chung Wang、Chieh-Kai Chan、Chien-Yu Lai

  DOI：10.1055/s-0039-1690088

  日期：2020.6

  An efficient and eco-friendly synthetic route for Friedländer quinoline synthesis of polysubstituted quinolines is described. This green chemical method starts from various 2-aminobenzophenones and mono- or dicarbonyl synthons and uses reusable Nafion NR50 material as a solid catalyst in ethanol under microwave irradiation. The protocol has a high generality of functional groups and provides the desired

  描述了一种用于弗里德兰德喹啉合成多取代喹啉的有效而环保的合成途径。这种绿色化学方法从各种2-氨基二苯甲酮和单或二羰基合成子开始，并在微波辐射下使用可重复使用的Nafion NR50材料作为乙醇中的固体催化剂。该方案具有很高的官能团通用性，并以良好或优异的产率提供了所需的喹啉。通过单晶X射线衍射分析确认了一些结构。
• Green synthesis of trimetallic oxide nanoparticles and their use as an efficient catalyst for the green synthesis of quinoline and spirooxindoles: Antibacterial, cytotoxicity and anti-colon cancer effects
  作者：Boshra Mahmoudi、Faezeh Soleimani、Hamideh Keshtkar、Mohammad Ali Nasseri、Milad Kazemnejadi

  DOI：10.1016/j.inoche.2021.108923

  日期：2021.11

  The three-metallic oxide (Cu/Cr/Ni) nanoparticles were prepared using Echinops persicus plant extract via a simple, biocompatible, cost-effective, and non-toxic procedure, and their catalytic activity was evaluated over the synthesis of biologically active quinoline and spirooxindole derivatives. The synthesized nanoparticles were characterized by various analytical methods including UV–Vis, FTIR,

  三金属氧化物 (Cu/Cr/Ni) 纳米粒子是使用刺猬植物提取物通过简单、生物相容性、成本效益高且无毒的方法制备的，并通过合成具有生物活性的喹啉和螺环吲哚衍生物。合成的纳米粒子通过各种分析方法进行表征，包括 UV-Vis、FTIR、EDX、XRD、FE-SEM、DLS 和 TEM 分析。反应中涉及的有效参数由Design-Expert 10.0.7软件设计。Cu/Cr/Ni纳米颗粒被用作在无溶剂条件下制备喹啉和螺吲哚的有效催化剂，具有良好到优异的效率。此外，由于含有丰富的酚类物质Echinops persicus花提取物、纳米粒子对大肠杆菌、金黄色葡萄球菌和蜡状芽孢杆菌的抗菌特性通过 MIC 以及扩散方法进行了研究。此外，基于 MTT 测定，在人结肠癌 (HT29) 细胞上研究了纳米颗粒的细胞毒性和抗结肠癌活性。结果和观察清楚地表明，Cu/Cr/Ni NPs 具有显着的催化和抗菌活性，完全优于其相应的单金属纳米粒子。
• 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。