4-(4-methoxyphenyl)-6-methylquinoline | 1395894-83-3

• 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: 4-(4-methoxyphenyl)-6-methylquinoline
• CAS: 1395894-83-3
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: BZORTJUWNLUAAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-对甲苯基-对甲苯磺胺 在 iron(III) chloride 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 0.5h， 生成 4-(4-methoxyphenyl)-6-methylquinoline
  参考文献：
  名称：

  Synthesis of substituted quinolines from N-aryl-N-(2-alkynyl)toluenesulfonamides via FeCl3-mediated intramolecular cyclization and concomitant detosylation

  摘要：

  A series of substituted quinolines have been synthesized in moderate to good yields (55-81%) from easily available substrates N-aryl-N-(2-alkynyl)toluenesulfonamides via FeCl3-mediated intramolecular cyclization and concomitant detosylation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.047

文献信息

• Transition-Metal-Free Approach for the Synthesis of 4-Aryl-quinolines from Alkynes and Anilines
  作者：Mandalaparthi Phanindrudu、Sandip Balasaheb Wakade、Dipak Kumar Tiwari、Pravin R. Likhar、Dharmendra Kumar Tiwari

  DOI：10.1021/acs.joc.8b01204

  日期：2018.8.17

  An efficient and transition-metal-free approach for the synthesis of 4-arylquinolines from readily available anilines and alkynes in the presence of K2S2O8 and DMSO has been developed. A variety of alkynes and anilines having a diverse range of substitution patterns can undergo the one-pot cascade process successfully. Effectively, this method uses DMSO as one carbon source, thus providing a highly

  在K 2 S 2 O 8和DMSO存在下，由苯胺和炔烃合成4-芳基喹啉的有效且无过渡金属的方法已得到开发。具有不同取代模式范围的各种炔烃和苯胺可以成功地经历一锅级联过程。有效地，该方法使用DMSO作为一种碳源，从而为合成4-芳基喹啉提供了一种极富原子经济性和环境友好性的方法。
• Synthesis of quinolines from anilines, acetophenones and DMSO under air
  作者：Tao-Shan Jiang、Xi Wang、Xiuli Zhang

  DOI：10.1016/j.tetlet.2018.06.054

  日期：2018.8

  An efficient CH3SO3H-promoted synthesis of quinolines from readily available anilines, acetophenones and DMSO under air is reported. This protocol gives diverse substituted 4-arylquinolines in moderate to high yields with broad substrate/functional group tolerance. Preliminary mechanistic studies demonstrate that DMSO may be transformed to HCHO in this process and used as a one carbon source.

  据报道，在空气中，CH 3 SO 3 H有效地促进了苯胺，苯乙酮和DMSO的喹啉合成。该方案以中等至高产率提供了多种取代的4-芳基喹啉，具有宽的底物/官能团耐受性。初步的机理研究表明，DMSO在此过程中可能转化为HCHO，并用作一种碳源。
• Oxidative Annulations Involving DMSO and Formamide: K₂S₂O₈ Mediated Syntheses of Quinolines and Pyrimidines
  作者：Santosh D. Jadhav、Anand Singh

  DOI：10.1021/acs.orglett.7b02838

  日期：2017.10.20

  An efficient strategy toward 4-arylquinolines and 4-arylpyrimidines from readily available precursors is described. Oxidative annulation promoted by K2S2O8 involving anilines, aryl ketones, and DMSO as a methine (═CH−) equivalent leads to 4-arylquinolines via a cascade that entails generation of a sulfenium ion, subsequent C–N and C–C bond formations, and cyclization. The application of this strategy

  描述了从容易获得的前体制备4-芳基喹啉和4-芳基嘧啶的有效策略。K 2 S 2 O 8促进的涉及苯胺，芳基酮和DMSO的亚甲基（═CH-）等效的氧化环化反应通过级联反应生成4-芳基喹啉，该级联反应会生成generation离子，随后的C–N和C– C键的形成和环化。还描述了该策略在乙酰苯甲酰胺甲酰胺偶联物的活化中对4-芳基嘧啶合成的应用。