2-(benzo[d][1,3]dioxol-5-yl)-6-methoxy-4-phenylquinoline | 1311140-68-7

• 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-(benzo[d][1,3]dioxol-5-yl)-6-methoxy-4-phenylquinoline
• 英文别名: 2-(1,3-Benzodioxol-5-yl)-6-methoxy-4-phenylquinoline；2-(1,3-benzodioxol-5-yl)-6-methoxy-4-phenylquinoline
• CAS: 1311140-68-7
• 化学式: C₂₃H₁₇NO₃
• 分子量: 355.393
• InChiKey: MBIBNYMCJLSHFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙烯 、 N-(benzo[d][1,3]dioxol-5-ylmethyl)-4-methoxyaniline 在 氧气 、 tris(p-bromophenylammoniumyl) hexachloroantimonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以53%的产率得到2-(benzo[d][1,3]dioxol-5-yl)-6-methoxy-4-phenylquinoline
  参考文献：
  名称：

  Oxidative Povarov Reaction via sp³ C–H Oxidation of N-Benzylanilines Induced by Catalytic Radical Cation Salt: Synthesis of 2,4-Diarylquinoline Derivatives

  摘要：

  Oxidative Povarov reaction of N-benzylanilines was realized under catalytic radical cation salt induced conditions. The mechanism studies revealed that a radical intermediate was involved in this catalytic oxidation. This method provides a new way to synthesize 2,4-diarylquinoline derivatives.

  DOI：

  10.1021/acs.orglett.5b00244

文献信息

• Molecular iodine-catalyzed and air-mediated tandem synthesis of quinolines via three-component reaction of amines, aldehydes, and alkynes
  作者：Xuejian Li、Zhenjun Mao、Yanguang Wang、Weixiang Chen、Xufeng Lin

  DOI：10.1016/j.tet.2011.03.087

  日期：2011.5

  A one-pot synthesis of quinolines via molecular iodine-catalyzed and air-mediated tandem condensation/imino-Diels–Alder/isomerization/oxidation of simple readily available amines, aldehydes, and alkynes has been developed. This methodology was extended to synthesize quinazolines from two molecules of amines and two molecules of glyoxalates.

  已经开发了通过分子碘催化和空气介导的串联缩合/亚氨基-狄尔斯-阿尔德/异构化/简单易得的胺，醛和炔烃的氧化一锅合成喹啉的方法。该方法被扩展为由两个分子的胺和两个分子的乙二醛酸酯合成喹唑啉。
• Oxidative Povarov Reaction via sp³ C–H Oxidation of <i>N</i>-Benzylanilines Induced by Catalytic Radical Cation Salt: Synthesis of 2,4-Diarylquinoline Derivatives
  作者：Jing Liu、Fang Liu、Yingzu Zhu、Xingge Ma、Xiaodong Jia

  DOI：10.1021/acs.orglett.5b00244

  日期：2015.3.20

  Oxidative Povarov reaction of N-benzylanilines was realized under catalytic radical cation salt induced conditions. The mechanism studies revealed that a radical intermediate was involved in this catalytic oxidation. This method provides a new way to synthesize 2,4-diarylquinoline derivatives.