1-[2-methyl-4-(4-fluorophenyl)quinolin-3-yl]ethanone

• 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: 1-[2-methyl-4-(4-fluorophenyl)quinolin-3-yl]ethanone
• 英文别名: 1-[4-(4-fluorophenyl)-2-methylquinolin-3-yl]ethan-1-one；1-[4-(4-Fluorophenyl)-2-methylquinolin-3-yl]ethanone
• 化学式: C₁₈H₁₄FNO
• 分子量: 279.314
• InChiKey: PJYHXUGXWNCROF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2-methyl-4-(4-fluorophenyl)quinolin-3-yl]ethanone 在 亚碘酰苯 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 9-(4-fluorophenyl)furo[3,4-b]quinolin-1(3H)-one
  参考文献：
  名称：

  Quinoline-Fused Lactones via Tandem Oxidation Cyclization: Metal-Free sp³ C–H Functionalization

  摘要：

  A unique lactonization of 2-methyl-3-acyl-4-phenylquinolines using PhIO as the oxidant and selectfluor as an additive is reported. The reaction occurs under ambient conditions through tandem oxidation and cyclization of sp³ C-H bonds under metal-free conditions. The heterocycle-fused lactones are obtained in moderate to good yield.

  DOI：

  10.1021/acs.joc.0c02238
• 作为产物：
  描述：

  2-氨基-4'-氟二苯甲酮 、 乙酰丙酮 在 对甲苯磺酸 作用下， 反应 0.05h， 以94%的产率得到1-[2-methyl-4-(4-fluorophenyl)quinolin-3-yl]ethanone
  参考文献：
  名称：

  在无溶剂条件下，对甲苯磺酸辅助快速有效合成多取代喹啉：微波辐射与常规加热的比较研究。

  摘要：

  在对甲苯磺酸的存在下，通过2-氨基芳基酮或2-氨基芳基醛与羰基化合物的弗里德兰德缩合反应，已经开发出一种快速有效的制备各种多取代喹啉的方法，该方法通过微波辐射和微波辐射来实现。在无溶剂条件下进行常规加热。

  DOI：

  10.1039/b513721g

文献信息

• Rapid and efficient synthesis of poly-substituted quinolines assisted by p-toluene sulphonic acid under solvent-free conditions: comparative study of microwave irradiation versus conventional heating
  作者：Cheng-Sheng Jia、Ze Zhang、Shu-Jiang Tu、Guan-Wu Wang

  DOI：10.1039/b513721g

  日期：——

  A rapid and efficient method for the preparation of various poly-substituted quinolines has been developed through the Friedlander condensation of 2-aminoarylketone or 2-aminoarylaldehyde with carbonyl compounds in the presence of p-toluene sulphonic acid, which was achieved by both microwave irradiation and conventional heating under solvent-free conditions.

  在对甲苯磺酸的存在下，通过2-氨基芳基酮或2-氨基芳基醛与羰基化合物的弗里德兰德缩合反应，已经开发出一种快速有效的制备各种多取代喹啉的方法，该方法通过微波辐射和微波辐射来实现。在无溶剂条件下进行常规加热。
• Oxidative coupling of 1-(2-methyl-4-phenylquinolin-3-yl)ethanone with ethanol and unexpected deacetylative synthesis of 3-hydroxy quinoline
  作者：Parul Chauhan、Makthala Ravi、Ruchir Kant、Prem. P. Yadav

  DOI：10.1039/c6ob02336c

  日期：——

  An efficient one pot method for the synthesis of anti-α,β-epoxy ketones from 1-(2-methyl-4-phenylquinolin-3-yl)ethanone and ethanol has been developed by a modified Darzen reaction. The reaction occurs under oxidative conditions via a cascade sequence of bromination, aldol condensation followed by substitution. The reaction in the presence of NBS and a base however, in the absence of an oxidant, led

  通过改良的Darzen反应，已经开发出一种由1-（2-甲基-4-苯基喹啉-3-基）乙酮和乙醇合成抗-α，β-环氧酮的有效的一锅法。该反应在氧化条件下通过溴化，醛醇缩合然后取代的级联序列发生。然而，在不存在氧化剂的情况下，在NBS和碱存在下的反应导致通过不寻常的重排形成相应的3-羟基化产物。
• Agrawal; Joshipura, Hardik M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 8, p. 1649 - 1652
  作者：Agrawal、Joshipura, Hardik M.

  DOI：——

  日期：——
• Benign and highly efficient synthesis of quinolines from 2-aminoarylketone or 2-aminoarylaldehyde and carbonyl compounds mediated by hydrochloric acid in water
  作者：Guan-Wu Wang、Cheng-Sheng Jia、Ya-Wei Dong

  DOI：10.1016/j.tetlet.2005.12.053

  日期：2006.2

  An environmentally friendly and highly efficient procedure for the preparation Of substituted quinoline derivatives was developed by a simple Friedlander reaction of 2-aminoarylketone or 2-aminoarylaldehyde with carbonyl compounds in the presence of hydrochloric acid utilizing water as the solvent. (c) 2005 Elsevier Ltd. All rights reserved.
• 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。