2-(4-methoxyphenyl)-6-methylquinoline | 199168-51-9

• 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: 2-(4-methoxyphenyl)-6-methylquinoline
• CAS: 199168-51-9
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: PQLJYPMDFWKOSF-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

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-6-methylquinoline 在 过氧化氢苯甲酰 、 氯仿 、 三氯氧磷 作用下， 生成 4-chloro-2-(4-methoxy-phenyl)-6-methyl-quinoline
  参考文献：
  名称：

  一些甲基喹啉图案化为atebrin的开放模型。

  摘要：

  DOI：

  10.1021/ja01214a044
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 2-(4-methoxyphenyl)-6-methylquinoline
  参考文献：
  名称：

  Kaku, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1927, p. 90; japan. Tl. S. 582

  摘要：

  DOI：

文献信息

• Visible-light-induced photoxidation-Povarov cascade reaction: synthesis of 2-arylquinoline through alcohol and <i>N</i>-benzylanilines under mild conditions <i>via</i> Ag/g-C₃N₄ nanometric semiconductor catalyst
  作者：Peng Wang、Xiaowen Wang、Xiyu Niu、Li Zhu、Xiaoquan Yao

  DOI：10.1039/d0cc00885k

  日期：——

  Ag/g-C3N4 nanometric semiconductor as the photocatalyst, 2-arylquinolines were synthesized through a photoxidation-Povarov cascade reaction of N-benzylanilines and alcohols under visible light irradiation. Under the blue light of a 3 W LED, good yields were achieved for various substrates in oxygen at room temperature. This methodology provides a green and mild alternative for the formation of 2-arylquinoline

  以Ag / g-C3N4纳米半导体为光催化剂，在可见光照射下，通过N-苄基苯胺和醇的光氧化-Povarov级联反应合成了2-芳基喹啉。在3 W LED的蓝光下，室温下在氧气中各种衬底的产率都很高。该方法为2-芳基喹啉衍生物的形成提供了绿色和温和的替代方法。值得注意的是，Ag / g-C3N4纳米复合材料可以方便地回收并以令人满意的产率重复使用数次。
• Facile synthesis of substituted quinolines by iron(<scp>iii</scp>)-catalyzed cascade reaction between anilines, aldehydes and nitroalkanes
  作者：Sachinta Mahato、Anindita Mukherjee、Sougata Santra、Grigory V. Zyryanov、Adinath Majee

  DOI：10.1039/c9ob01294j

  日期：——

  A library of substituted quinolines has been synthesized by the reaction of aldehydes, anilines and nitroalkanes using a catalytic amount of Fe(iii) chloride. The reaction is a simple, efficient, one-pot, three-component domino strategy in ambient air which afforded the products in high yields. A probable pathway of the reaction is a sequential aza-Henry reaction/cyclization/denitration. The use of

  通过醛，苯胺和硝基烷烃的催化反应，使用催化量的三价氯化铁（Fe（iii））合成了取代的喹啉文库。该反应是在环境空气中的一种简单，有效，一锅，三组分的多米诺骨牌策略，从而以高收率提供了产物。反应的可能途径是顺序的氮杂-亨利反应/环化/脱硝。使用可商购的化学品作为起始原料，廉价的金属催化剂，好氧反应条件，宽泛的官能团耐受性和操作简便性是本方案的显着优点。
• Three-Component Povarov Reaction with Alcohols as Alkene Precursors: Efficient Access to 2-Arylquinolines
  作者：Xinjian Li、Qi Xing、Pan Li、Jingjing Zhao、Fuwei Li

  DOI：10.1002/ejoc.201601343

  日期：2017.1.18

  An atom-economic and efficient approach to the synthesis of 2-arylquinolines has been developed. The protocol involves an iron-catalysed cascade N-alkylation/aerobic oxidation/Povarov reaction, and the desired quinolines were prepared in moderate to excellent yields from readily accessible anilines, aldehydes, and EtOH/nPrOH, with water as the only side-product. The aniline substrates also act as a

  已开发出一种原子经济且有效的合成 2-芳基喹啉的方法。该协议涉及铁催化的级联 N-烷基化/有氧氧化/Povarov 反应，所需的喹啉是从易于获得的苯胺、醛和 EtOH/nPrOH 中以中等至极好的收率制备的，水作为唯一的副产品。苯胺底物还通过原位 N-烷基化/氧化过程充当 EtOH/nPrOH 的可回收转移介质。这使得 EtOH/nPrOH 成为一种经济且环保的烯烃前体和溶剂。
• Iron-Catalyzed Aerobic Dehydrogenative Kinetic Resolution of Cyclic Secondary Amines
  作者：Ran Lu、Liya Cao、Honghao Guan、Lei Liu

  DOI：10.1021/jacs.9b00615

  日期：2019.4.17

  dehydrogenative kinetic resolution of cyclic secondary amines using air as an oxidant has been reported. The economical and practical method is applicable to a series of cyclic benzylic amines, including 5,6-dihydrophenanthridines and 1,2-dihydroquinolines, with diverse functional groups at the α position in high yields with excellent enantioselectivities. The direct dehydrogenative kinetic resolution of

  已经报道了使用空气作为氧化剂的环状仲胺的非酶促铁催化脱氢动力学拆分。该方法经济实用，适用于5,6-二氢菲啶和1,2-二氢喹啉等一系列α位官能团多样的环状苄胺，收率高，对映选择性好。还证明了使用现有催化不对称合成策略难以获得的生物活性分子的高级中间体的直接脱氢动力学拆分。
• A Domino Heck Coupling–Cyclization–Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines
  作者：Santanu Ghora、Chinnabattigalla Sreenivasulu、Gedu Satyanarayana

  DOI：10.1055/a-1589-7548

  日期：2022.1

  An efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence

  描述了通过钯催化促进的碘苯胺与烯丙醇的偶联来高效、单锅、多米诺合成喹啉。整个合成过程包括 2-碘苯胺和烯丙醇之间的分子间 Heck 偶联，原位生成的酮与内部胺官能团的分子内缩合，以及脱氢序列。值得注意的是，该协议以绿色溶剂的形式出现在水中。值得注意的是，该方法具有广泛的底物范围，可用于通过氘交换过程合成氘化喹啉。