8-methoxy-4-phenylquinoline | 63352-82-9

• 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: 8-methoxy-4-phenylquinoline
• CAS: 63352-82-9
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: JLYMXRHCMCKHFI-UHFFFAOYSA-N

物化性质

• 沸点：
  390.4±30.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  8-methoxy-4-phenyl-1,2,3,4-tetrahydroquinoline 在 氧气 、 sodium t-butanolate 作用下， 以 二甲基亚砜 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以78%的产率得到8-methoxy-4-phenylquinoline
  参考文献：
  名称：

  DMSO / t-BuONa / O2介导的饱和N-杂环的好氧脱氢。

  摘要：

  芳族N-杂环如喹啉，异喹啉和二氢吲哚是通过叔丁醇钠促进的DMSO溶液中饱和杂环的氧化脱氢而合成的。该反应在温和的反应条件下进行并且具有良好的官能团耐受性。机理研究表明，一种自由基途径涉及从底物的N–H键或α–C–H夺取二甲基自由基的氢以及随后氮或α-氨基烷基自由基的氧化。

  DOI：

  10.1021/acs.joc.9b03447

文献信息

• Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines
  作者：Jin Yuan、Jin-Tao Yu、Yan Jiang、Jiang Cheng

  DOI：10.1039/c6ob02714h

  日期：——

  A palladium-catalyzed annulation of ortho-vinylanilines with dimethyl sulfoxide was developed to access 4-aryl quinolines in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “CH–” fragment in this transformation. It represents a facile pathway leading to 4-aryl quinolines.

  开发了钯催化的邻-乙烯基苯胺与二甲基亚砜的环化反应，以中等至良好的产率获得了4-芳基喹啉。DMSO由1,4-二氮杂双环[2.2.2]辛烷双（二氧化硫）加合物（DABSO）激活，在此转化中充当“ CH–”片段。它代表了导致4-芳基喹啉的简便途径。
• Copper-mediated formal [5+1] annulation of 2-vinylanilines and glyoxylic acid: A facile approach for the synthesis of 4-arylated quinolines
  作者：Yunyu Xiang、Puying Luo、Tianxin Hao、Weikang Xiong、Xiaolin Song、Qiuping Ding

  DOI：10.1016/j.tet.2020.131832

  日期：2021.1

  A copper-mediated formal [5 + 1] oxidative annulation of 2-vinylanilines and glyoxylic acid to 4-arylated quinolines was developed. A series of 4-arylated quinoline derivatives were obtained in good to excellent yields. This protocol could be carried out efficiently on gram scale. The transformation probably underwent nucleophilic addition/6π electrocyclization/oxidative aromatization and the elimination

  开发了铜介导的2-乙烯基苯胺和乙醛酸的正式[5 +1]氧化环化成4-芳基化的喹啉。获得了一系列4-芳基化的喹啉衍生物，收率良好至优异。该协议可以在克规模上有效地执行。该转化可能经历了亲核加成/6π电环化/氧化芳构化和消除了CO 2级联过程。
• Palladium-catalysed cross-coupling reactions of arylboronic acids with π-deficient heteroaryl chlorides
  作者：Naji M. Ali、Alexander McKillop、Michael B. Mitchell、Ricardo A. Rebelo、Philip J. Wallbank

  DOI：10.1016/s0040-4020(01)80481-6

  日期：1992.1

  The palladium-catalysed cross-coupling reactions of arylboronic acids with a variety of pi-deficient heteroaryl chlorides proceed in high yield. [1,4-Bis(diphenylphosphino)butane]palladium(II) dichloride was found to be a very satisfactory catalyst for monocyclic heteroaryl chlorides, whereas tetrakis(triphenylphosphine)palladium(O) was found to be excellent for a range of chloroquinoline derivatives.
• A New Synthesis of 4-Phenylquinolines by Reaction of 2-(a-Bromobenzyl)oxiranes with Aniline Derivatives
  作者：Michinori Karikomi、Hiroshi Tsukada、Takashi Toda

  DOI：10.3987/com-01-9234

  日期：——

  Several 4-phenylquinoline derivatives were synthesized by reaction of (2R*,1 'R*)-2-(alpha -bromobenzyl)oxiranes (1a) with aniline derivatives, and the following treatment of the formed 3-hydroxy-4-phenyl-1,2,3,4-tetrahydroquinolines (2) with the Rydon reagent, and potassium t-butoxide and air oxidation.