3-benzylamino-2-phenylquinazolinone | 81107-41-7

• 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: 3-benzylamino-2-phenylquinazolinone
• 英文别名: 3-(benzylamino)-2-phenylquinazolin-4(3H)-one；3-(Benzylamino)-2-phenylquinazolin-4-one
• CAS: 81107-41-7
• 化学式: C₂₁H₁₇N₃O
• 分子量: 327.385
• InChiKey: DXHSEUQUNQRHMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻氨基苯甲酸 以 溶剂黄146 为溶剂， 生成 3-benzylamino-2-phenylquinazolinone
  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

• QUINAZOLINONE MODULATORS OF TGR5
  申请人：Pinkerton Anthony B.

  公开号：US20090035306A1

  公开（公告）日：2009-02-05

  The present invention relates to quinazolinone compounds useful as modulators of TGR5 and methods for the treatment or prevention of metabolic, cardiovascular, and inflammatory diseases.

  本发明涉及喹唑酮类化合物，可用作TGR5调节剂，并用于治疗或预防代谢性、心血管和炎症性疾病的方法。
• Palladium-Catalyzed Cascade Reaction of 2-Amino-<i>N</i>′-arylbenzohydrazides with Triethyl Orthobenzoates To Construct Indazolo[3,2-<i>b</i>]quinazolinones
  作者：Weiguang Yang、Rui Qiao、Jiuxi Chen、Xiaobo Huang、Miaochang Liu、Wenxia Gao、Jinchang Ding、Huayue Wu

  DOI：10.1021/jo5024848

  日期：2015.1.2

  A palladium-catalyzed sequential cyclization/C-H activation cascade reaction of 2-amino-N'-arylbenzohydrazides with triethyl orthobenzoates has been developed, providing indazolo[3,2-b]quinazolinones in good to high yields. Two key intermediates of the reaction, 2-phenyl-3-(phenylamino)quinazolinone and C-H insertion palladacycle, were isolated, and their structures were unambiguously confirmed by X-ray crystallography. This method represents an unprecedented example of a halogen-free protocol to access indazolo[3,2-b]quinazolinones. Moreover, this chemistry also provides a useful tool for the discovery of fluorescent materials.
• ABOUL-ENEIN M. N.; EID A. I., PHARMAC. ACTA HELV., 1981, 56, NO 8, 239-240
  作者：ABOUL-ENEIN M. N.、 EID A. I.

  DOI：——

  日期：——
• [EN] QUINAZOLINONE MODULATORS OF TGR5<br/>[FR] MODULATEURS QUINAZOLINONES DE TGR5
  申请人：KALYPSYS INC

  公开号：WO2008067219A2

  公开（公告）日：2008-06-05

  [EN] The present invention relates to quinazolinone compounds useful as modulators of TGR5 and methods for the treatment or prevention of metabolic, cardiovascular, and inflammatory diseases.
  [FR] Cette invention concerne des composés quinazolinones utilisés en tant que modulateurs de TGR5 ainsi que des méthodes permettant de traiter ou de prévenir des maladies métaboliques, cardiovasculaires et inflammatoires.
• 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.