N-phenyl-2-(p-tolyl)-1,2-dihydroquinazolin-4-amine | 1262424-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-phenyl-2-(p-tolyl)-1,2-dihydroquinazolin-4-amine
• 英文别名: 2-(4-methylphenyl)-N-phenyl-1,2-dihydroquinazolin-4-amine
• CAS: 1262424-46-3
• 化学式: C₂₁H₁₉N₃
• 分子量: 313.402
• InChiKey: BKPOFCOBUSHADH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  36.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenyl-2-(p-tolyl)-1,2-dihydroquinazolin-4-amine 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 以60%的产率得到N-phenyl-2-(p-tolyl)quinazolin-4-amine
  参考文献：
  名称：

  Iodine-promoted facile synthesis of new (+)-2,3-dihydro-N,2-diarylquinazolines

  摘要：

  The reactivity of 2-amino-N'-arylbenzamidines 1a-e towards p-tolualdehyde 2a and 1-naphthaldehyde 2b under the catalytic influence of commercial iodine at ambient temperature has been examined. New chiral quinazolines 3a-e and 4a-d have been identified as reaction products. These products have subsequently been oxidised to N,2-diarylquinazolin-4-amines 12, 13a-d. The structures of the products were elucidated by their NMR, mass and IR spectra in addition to elemental analyses. The structure of 3e was further confirmed by X-ray structural analysis. The mechanism of formation of 3a-e and 4a-d is discussed.

  DOI：

  10.3998/ark.5550190.0011.a09
• 作为产物：
  描述：

  靛红酸酐 在 叔丁基过氧化氢 、 碘 作用下， 以 水 为溶剂， 反应 12.25h， 生成 N-phenyl-2-(p-tolyl)-1,2-dihydroquinazolin-4-amine
  参考文献：
  名称：

  在非金属催化氧化系统中通过激活 sp3 CH 键在一锅中三组分多米诺合成 2-Arylquinazoline-4-amines

  摘要：

  非金属催化氧化系统 I2/叔丁基过氧化氢 (TBHP) 已前所未有地应用于三组分多米诺骨牌反应，同时开发了一种简单有效的方案来新合成 2-芳基-N-取代的喹唑啉-4-胺在一个锅中，由靛红酸酐、芳香胺和另一种含有与氮相邻的亚甲基的胺组成。该协议是新的和实用的，因为在胺 2 或 3 上取代的给电子和吸电子基团都可以存活并以合理的产率提供相应的产品。与逐步程序不同，碘对于三组分一锅反应至关重要。

  DOI：

  10.1002/ejoc.201101315

文献信息

• Three-Component Domino Synthesis of 2-Arylquinazoline-4-amines in One Pot by Activating an sp3 C-H Bond in a Nonmetal Catalytic Oxidation System
  作者：Li-Yan Zeng、Wen-Bin Yi、Chun Cai

  DOI：10.1002/ejoc.201101315

  日期：2012.1

  The nonmetal catalytic oxidation system I2/tert-butyl hydroperoxide (TBHP) has been unprecedentedly applied to a three-component domino reaction and simultaneously a simple and efficient protocol has been developed to newly synthesize 2-aryl-N-substitutied quinazoline-4-amines in one pot from isatoic anhydride, aromatic amine, and another amine containing methylene adjacent to nitrogen. This protocol

  非金属催化氧化系统 I2/叔丁基过氧化氢 (TBHP) 已前所未有地应用于三组分多米诺骨牌反应，同时开发了一种简单有效的方案来新合成 2-芳基-N-取代的喹唑啉-4-胺在一个锅中，由靛红酸酐、芳香胺和另一种含有与氮相邻的亚甲基的胺组成。该协议是新的和实用的，因为在胺 2 或 3 上取代的给电子和吸电子基团都可以存活并以合理的产率提供相应的产品。与逐步程序不同，碘对于三组分一锅反应至关重要。
• Iodine-promoted facile synthesis of new (+)-2,3-dihydro-N,2-diarylquinazolines
  作者：Kamal M. El-Shaieb、Henning Hopf、Peter G. Jones

  DOI：10.3998/ark.5550190.0011.a09

  日期：——

  The reactivity of 2-amino-N'-arylbenzamidines 1a-e towards p-tolualdehyde 2a and 1-naphthaldehyde 2b under the catalytic influence of commercial iodine at ambient temperature has been examined. New chiral quinazolines 3a-e and 4a-d have been identified as reaction products. These products have subsequently been oxidised to N,2-diarylquinazolin-4-amines 12, 13a-d. The structures of the products were elucidated by their NMR, mass and IR spectra in addition to elemental analyses. The structure of 3e was further confirmed by X-ray structural analysis. The mechanism of formation of 3a-e and 4a-d is discussed.