6-methoxy-2-(4-nitrophenyl)-4-phenylquinoline | 73402-98-9

• 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: 6-methoxy-2-(4-nitrophenyl)-4-phenylquinoline
• 英文别名: 6-methoxy-2-(4-nitro-phenyl)-4-phenyl-quinoline；6-Methoxy-4-phenyl-2-(p-nitrophenyl)-chinolin
• CAS: 73402-98-9
• 化学式: C₂₂H₁₆N₂O₃
• 分子量: 356.381
• InChiKey: UPDZQHLWYRWACV-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  539.7±50.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

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：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 (E)-4-methoxy-N-(4-nitrobenzylidene)aniline 在 三氟甲磺酸 、 manganese triacetate 作用下， 以 乙腈 、 溶剂黄146 为溶剂， 反应 27.0h， 以80%的产率得到6-methoxy-2-(4-nitrophenyl)-4-phenylquinoline
  参考文献：
  名称：

  Synthesis of Aryl-substituted Quinoline Derivatives via Brønsted Acid-catalyzed [4+2] Aza Diels–Alder Reaction

  摘要：

  CF3SO3H 催化的醛亚胺与硅烯醇醚的 [4+2] 氮杂狄尔斯-阿尔德反应以及随后的原位氧化以良好至优异的收率提供了喹啉衍生物，其中使用 CF3SO3H 作为布朗斯台德酸对于环化反应至关重要。

  DOI：

  10.1246/cl.2004.922

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.
• Photosensitized Diels–Alder reactions of N-arylimines: synthesis of tetrahydroquinoline derivatives
  作者：Wei Zhang、Xiaodong Jia、Li Yang、Zhong-Li Liu

  DOI：10.1016/s0040-4039(02)02328-6

  日期：2002.12

  Irradiation (lambda>345 nm) of catalytic amounts of 2,4,6-triphenylpyrylium tetrafluoroborate (TPT) in a CH2Cl2 solution of N-aryl imines and alpha-methyl styrene or styrene produced the corresponding [4+2] cycloaddition products, tetrahydroquinoline derivatives, in good yield. The reaction was controlled by the relative oxidation potentials of the dienophile and the diene. (C) 2002 Elsevier Science Ltd. All rights reserved.
• MIYAJIMA SHINGO; ITO KUNIO; KASHIWAGURA ISAO; KITAMURA CHOJI, NIXON KAGAKU KAJSI, NIRRON KAGAKU KAISNI, J. CHEM. SOS. JAR., CHEM. AND I+
  作者：MIYAJIMA SHINGO、 ITO KUNIO、 KASHIWAGURA ISAO、 KITAMURA CHOJI

  DOI：——

  日期：——
• Synthesis of Aryl-substituted Quinoline Derivatives via Brønsted Acid-catalyzed [4+2] Aza Diels–Alder Reaction
  作者：Takahiko Akiyama、Saeko Nakashima、Koji Yokota、Kohei Fuchibe

  DOI：10.1246/cl.2004.922

  日期：2004.7

  CF3SO3H-catalyzed [4+2] aza Diels–Alder reaction of aldimines with silyl enol ethers, and subsequent in situ oxidation furnished quinoline derivatives in good to excellent yields, wherein use of CF3SO3H as a Brønsted acid is critical for the cyclization reaction.

  CF3SO3H 催化的醛亚胺与硅烯醇醚的 [4+2] 氮杂狄尔斯-阿尔德反应以及随后的原位氧化以良好至优异的收率提供了喹啉衍生物，其中使用 CF3SO3H 作为布朗斯台德酸对于环化反应至关重要。