phenyl(4-phenylquinolin-3-yl)methanone | 113058-27-8

• 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: phenyl(4-phenylquinolin-3-yl)methanone
• 英文别名: Phenyl-(4-phenylquinolin-3-yl)methanone
• CAS: 113058-27-8
• 化学式: C₂₂H₁₅NO
• 分子量: 309.367
• InChiKey: AFDFKFUEUUCJOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-喹啉羰酰氯 在 三氯化铝 、 乙醚 、 1,1,2,2-四氯乙烷 作用下， 生成 phenyl(4-phenylquinolin-3-yl)methanone
  参考文献：
  名称：

  The Condensation of Grignard Reagents with 3-Pyridyl and 3-Quinolyl Ketones

  摘要：

  DOI：

  10.1021/ja01570a046

文献信息

• Chemoselective Synthesis of N-Arylenaminones and 3-Aroylquinolines by Synergistic Control of Temperature and Amount of Catalyst
  作者：Fuchao Yu、Pan Zhou、Biao Hu、Kairui Rao、Lingdan Li、Jiao Yang、Chuanzhu Gao、Fengping Wang

  DOI：10.1055/s-0036-1590950

  日期：2018.3

  An efficient and practical method has been developed for the divergent synthesis of N-arylenaminones and 3-aroylquinolines from 2-aminoaryl ketones and N,N-dimethylenaminones in the presence of 4-toluenesulfonic acid through synergistic control of the temperature and amount of catalyst. Furthermore, gram-scale synthesis and synthetic applications have been evaluated. Features of this protocol include controllable results, mild conditions, good functional-group tolerance, operational simplicity, and excellent yields.

  已经开发出一种高效实用的方法，通过温度和催化剂量的协同控制，在4-甲苯磺酸存在下，从2-氨基芳基酮和N,N-二甲基亚胺酮合成N-芳基氨酮和3-芳酰喹啉。此外，还评估了克制级别合成和合成应用。该方案的特点包括可控的结果、温和的条件、良好的官能团容忍性、操作简单和出色的产率。
• ZnCl2-promoted Friedländer-type synthesis of 4-substituted 3-aroyl quinolines from o-aminoaryl ketones and enaminones
  作者：Laichun Luo、Zongbao Zhou、Jiayi Zhu、Xue Lu、Hong Wang

  DOI：10.1016/j.tetlet.2016.09.087

  日期：2016.11

  A practical synthesis of 4-substituted 3-aroyl quinolines via Friedländer-type reaction from readily available o-aminoaryl ketones and enaminones was developed. In the presence of ZnCl2, the reaction proceeded smoothly affording the desired products with various functional groups in moderate to good yields.

  通过容易获得的邻氨基芳基酮和烯胺酮的弗里德兰德型反应，开发了一种实用的合成4-取代的3-芳基喹啉的方法。在ZnCl 2的存在下，反应平稳进行，以中等至良好的产率提供具有各种官能团的所需产物。
• 一种3-酰基喹啉类化合物的合成方法
  申请人：河南师范大学

  公开号：CN106749020B

  公开（公告）日：2019-11-01

  本发明公开了一种3‑酰基喹啉类化合物的合成方法，属于有机合成技术领域。本发明的技术方案要点为：本发明简单高效，操作方便，条件温和且底物适用范围广。
• Visible-Light-Induced Cascade Cyclization of <i>N</i>-Propargyl Aromatic Amines and Acyl Oxime Esters: Rapid Access to 3-Acylated Quinolines
  作者：Man Zhang、Sixin Wu、Lei Wang、Ziqin Xia、Kaimo Kuang、Qiankun Xu、Fangli Zhao、Nengneng Zhou

  DOI：10.1021/acs.joc.2c01277

  日期：2022.8.5

  Visible-light-induced radical cascade acylation/cyclization/aromatization of N-propargyl aromatic amines and acyl oxime esters for the construction of 3-acylated quinolines is developed. This approach uses acyl oxime esters as the precursor of acyl radicals as well as acylation reagents, Eosin Y as the photocatalyst, and acetonitrile as the solvent, providing a convenient route toward 3-acylated quinolines

  开发了用于构建 3-酰化喹啉的N-炔丙基芳胺和酰基肟酯的可见光诱导自由基级联酰化/环化/芳构化。该方法使用酰基肟酯作为酰基自由基的前体以及酰化试剂，曙红 Y 作为光催化剂，乙腈作为溶剂，为通过酰基肟酯的 C-C 键断裂获得 3-酰化喹啉提供了一条便捷的途径.
• Iron-catalyzed cascade reaction of ynone with o-aminoaryl compounds: a Michael addition–cyclization approach to 3-carbonyl quinolines
  作者：Hongfeng Li、Xiaolei Xu、Jingyu Yang、Xin Xie、He Huang、Yanzhong Li

  DOI：10.1016/j.tetlet.2010.11.106

  日期：2011.1

  An efficient iron-catalyzed cascade Michael addition-cyclization of o-aminoaryl compounds including o-aminoaryl aldehydes, o-aminoaryl ketones, and o-aminobenzyl alcohols with ynones for the synthesis of 3-carbonyl quinolines is reported. The reactions proceed to afford 3-carbonyl quinoline derivatives with or without substituent at the C-4 position in good to high yields using Iron(III) chloride hexahydrate as the catalyst in the air. (C) 2010 Elsevier Ltd. All rights reserved.