6-chloro-2-(4-chlorophenyl)-4-phenylquinoline | 21923-45-5

• 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-chlorophenyl)-4-phenylquinoline
• CAS: 21923-45-5
• 化学式: C₂₁H₁₃Cl₂N
• 分子量: 350.247
• InChiKey: DRQSSQYBPLZPMA-UHFFFAOYSA-N

物化性质

• 熔点：
  159-160 °C
• 沸点：
  495.8±45.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  C₂₁H₁₃Cl₂N*Cl₆Sb^(1-)*H⁽¹⁺⁾ 在 sodium hydroxide 作用下， 反应 2.0h， 以76%的产率得到6-chloro-2-(4-chlorophenyl)-4-phenylquinoline
  参考文献：
  名称：

  On the Reaction ofN-Arylnitrilium Salts with Acetylenes: Synthesis of Substituted Quinolines

  摘要：

  喹啉盐 3 由 N-芳基硝基盐 1 与乙炔 2 反应生成。在水基作用下，盐 3 转化为相应的喹啉 4。

  DOI：

  10.1055/s-1992-26250

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。
• Ionic Liquid-Promoted Regiospecific Friedlander Annulation:  Novel Synthesis of Quinolines and Fused Polycyclic Quinolines
  作者：Sanjay S. Palimkar、Shapi A. Siddiqui、Thomas Daniel、Rajgopal. J. Lahoti、Kumar V. Srinivasan

  DOI：10.1021/jo035153u

  日期：2003.11.1

  Several room-temperature ionic liquids (ILs) based on 1-butylimidazolium salts with varying anions were synthesized and evaluated for the preparation of biologically active substituted quinolines and fused polycyclic quinolines using the Friedlander heteroannulation reaction. On screening, 1-butylimidazolium tetrafluoroborate [Hbim]BF4 was found to be the best ionic liquid for the heteroannulation reaction

  合成了几种基于具有不同阴离子的1-丁基咪唑鎓盐的室温离子液体（ILs），并使用Friedlander杂环化反应评估了它们的生物活性取代喹啉和稠合多环喹啉的制备。筛选时，发现四氟硼酸1-丁基咪唑鎓[Hbim] BF4是异环化反应的最佳离子液体，并对此现象的原因进行了很好的解释。该反应在相对温和的条件下进行得很好，没有添加任何催化剂。IL充当该区域特异性合成的启动子，可以循环使用。通过这种绿色方法，可以制备出具有优异收率和纯度且特性良好的各种喹啉。
• 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。
• 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。
• Magnetic Fe–Cr–Ni oxide alloy nano-belts prepared from the chemical decomposition of a stainless steel screw (a top-down approach): an efficient and cheap catalyst for multicomponent reactions
  作者：Milad Kazemnejadi、Zeinab Sharafi、Boshra Mahmoudi、Atefeh Zeinali、Mohammad Ali Nasseri

  DOI：10.1007/s13738-019-01814-z

  日期：2020.4

  A new, cheap, and accessible method has been used for the preparation of nano-belts from the chemical decomposition (top-down approach) of a cheap stainless steel screw and found as an efficient magnetically recyclable nanocatalyst for the preparation of quinolines and 1,8-dioxo-octahydroxanthenes under mild reaction conditions. The nano-belts, Fe–Cr–Ni oxide alloy, was prepared in a two-step synthesis and characterized with various instrumental methods. Due to magnetic property of the screw (a ferritic-alloy), the resultant nano-belts is magnetic. Magnetic Fe–Cr–Ni alloy nano-belts were applied toward efficient preparation of quinolines and 1,8-dioxo-octahydroxanthenes under mild conditions. The catalyst could be readily recovered and recycled for several consecutive runs, while it suffers from a very low metal leaching and subsequently efficiency drop.

  一种新的、廉价且易得的方法已被用于从廉价不锈钢螺丝的化学分解（自上而下的方法）中制备纳米带，并发现其在温和反应条件下作为高效的磁性可回收纳米催化剂，用于喹啉和1,8-二氧杂-八氢氧杂蒽的制备。这种纳米带，即Fe–Cr–Ni氧化物合金，是通过两步合成法制备的，并使用多种仪器方法进行了表征。由于螺丝（一种铁素体合金）的磁性特性，所得纳米带也具有磁性。磁性Fe–Cr–Ni合金纳米带在温和条件下被应用于高效制备喹啉和1,8-二氧杂-八氢氧杂蒽。该催化剂可以轻易地回收并在多次连续运行中循环使用，同时金属溶出现象极少，因此催化效率几乎不会下降。

表征谱图