4-(2-methoxyphenyl)quinoline | 145618-83-3

• 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-(2-methoxyphenyl)quinoline
• CAS: 145618-83-3
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: YJFTVZHNTJVPKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  355.7±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)：
  3.91
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-(2-methoxyphenyl)-1-tosyl-1,4-dihydroquinoline 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以92%的产率得到4-(2-methoxyphenyl)quinoline
  参考文献：
  名称：

  Synthesis of Quinolines from N-Tosyl-1-azadienes

  摘要：

  A route to aryl-substituted quinolines from N-tosyl 1-azadienes is described. The key steps are a [4+2] cycloaddition with benzyne followed by base treatment of the 1,4-dihydroquinoline product. The N-tosyl 1-azadienes were prepared from readily accessible cinnamaldehyde and chalcone substrates by condensation with p-TsNH2. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.726388

文献信息

• 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。