3-fluoro-5-phenylindazolo[3,2-b]quinazolin-7(5H)-one | 1437780-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-fluoro-5-phenylindazolo[3,2-b]quinazolin-7(5H)-one
• 英文别名: 3-fluoro-5-phenylindazol[3,2-b]quinazolin-7(5H)-one；3-Fluoro-5-phenylindazolo[3,2-b]quinazolin-7-one；3-fluoro-5-phenylindazolo[3,2-b]quinazolin-7-one
• CAS: 1437780-31-8
• 化学式: C₂₀H₁₂FN₃O
• 分子量: 329.333
• InChiKey: CQZUPFJCZSHZNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-氟苯基)-4H-3,1-苯并噁嗪-4-酮 在 氧气 、 palladium diacetate 、 碳酸氢钠 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.17h， 生成 3-fluoro-5-phenylindazolo[3,2-b]quinazolin-7(5H)-one
  参考文献：
  名称：

  Pd-Catalyzed Intramolecular Aerobic Oxidative C–H Amination of 2-Aryl-3-(arylamino)quinazolinones: Synthesis of Fluorescent Indazolo[3,2-b]quinazolinones

  摘要：

  A palladium-catalyzed intramolecular aerobic oxidative C-H amination of 2-aryl-3-(arylamino)quinazolinones has been developed, providing a variety of substituted indazolo[3,2-b]quinazolinone derivatives in moderate to excellent yields. Preliminary mechanistic studies suggested that a palladacycle dimer could be the key intermediate, which underwent a cascade "rollover" cyclometalation and C-H amination sequence. Furthermore, the potential utility of these products has been demonstrated as a new class of blue fluorophores for fluorescent materials.

  DOI：

  10.1021/ol5026553

文献信息

• 一种酸性条件下合成喹唑啉酮并吲唑衍生物的 方法
  申请人：温州大学

  公开号：CN103980280B

  公开（公告）日：2016-05-04

  本发明涉及一种喹唑啉酮并吲唑衍生物的合成方法，所述合成方法在催化剂和氧化剂存在下，于酸性有机溶剂中，2-芳基-3-芳氨基喹唑啉酮衍生物发生分子内脱氢偶联反应，从而得到了结构多样化的喹唑啉酮并吲唑衍生物。所述方法通过催化剂、氧化剂和酸性有机溶剂的协同使用，而实现了一锅法高效合成喹唑啉酮并吲唑衍生物的反应，具有高效、环境友好、收率和纯度高等诸多优点，具有良好的研究价值和应用前景。
• Copper(I)-Catalyzed Synthesis of 5-Arylindazolo[3,2-<i>b</i>]quinazolin-7(5<i>H</i>)-one via Ullmann-Type Reaction
  作者：Dong-Sheng Chen、Guo-Lan Dou、Yu-Ling Li、Yun Liu、Xiang-Shan Wang

  DOI：10.1021/jo400420b

  日期：2013.6.7

  The treatment of 2-amino-N'-arylbenzohydrazide and o-halogenated benzaldehyde in the presence of CuBr and Cs2CO3 gave 5-arylindazolo[3,2-b]quinazolin-7(5H)-one in high yields. This procedure contains an Ullmann-type reaction and provides an efficient method to construct fused tetracyclic heterocycles.
• Pd-Catalyzed Intramolecular Aerobic Oxidative C–H Amination of 2-Aryl-3-(arylamino)quinazolinones: Synthesis of Fluorescent Indazolo[3,2-<i>b</i>]quinazolinones
  作者：Weiguang Yang、Jiuxi Chen、Xiaobo Huang、Jinchang Ding、Miaochang Liu、Huayue Wu

  DOI：10.1021/ol5026553

  日期：2014.10.17

  A palladium-catalyzed intramolecular aerobic oxidative C-H amination of 2-aryl-3-(arylamino)quinazolinones has been developed, providing a variety of substituted indazolo[3,2-b]quinazolinone derivatives in moderate to excellent yields. Preliminary mechanistic studies suggested that a palladacycle dimer could be the key intermediate, which underwent a cascade "rollover" cyclometalation and C-H amination sequence. Furthermore, the potential utility of these products has been demonstrated as a new class of blue fluorophores for fluorescent materials.