2-(3,5-di-tert-butyl-2-hydroxyphenyl)quinazolin-4(3H)-one | 1373882-14-4

• 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: 2-(3,5-di-tert-butyl-2-hydroxyphenyl)quinazolin-4(3H)-one
• 英文别名: 2-(2-hydroxy-3,5-di(t-butyl)phenyl)-3H-quinazolin-4-one；2-(3,5-ditert-butyl-2-hydroxyphenyl)-3H-quinazolin-4-one
• CAS: 1373882-14-4
• 化学式: C₂₂H₂₆N₂O₂
• 分子量: 350.461
• InChiKey: PFVBDJWNAPXUQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,5-di-tert-butyl-2-hydroxyphenyl)quinazolin-4(3H)-one 在 三氟化硼乙醚 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 0.08h， 以87%的产率得到2-(2-hydroxy-3,5-di(t-butyl)phenyl)-3H-quinazolin-4-onatoboron difluoride
  参考文献：
  名称：

  Synthesis, structure and photoluminescent properties of BF2 and BPh2 complexes with N,O-benzazine ligands

  摘要：

  Novel N,O-bidentate BF2 and BPh2 complexes have been prepared in good to excellent yields through coordination of 8-hydroxy-2-methylquinolines and 2-(2-hydroxyphenyl)-3H-quinazolin-4-ones with boron trifluoride etherate or triphenylborane under mild conditions. All complexes have been characterized by H-1, B-11 and F-19 NMR, mass-spectrometry and X-ray crystallography data. Some complexes have been found to exhibit a significant fluore.scence in acetonitrile solutions. Electronic and site effects of substituents in both heterocyclic and phenol fragments proved to have a profound impact on quantum yields. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.04.010
• 作为产物：
  描述：

  3,5-二叔丁基水杨醛 在 copper dichloride 作用下， 以 乙醇 为溶剂， 反应 6.5h， 生成 2-(3,5-di-tert-butyl-2-hydroxyphenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis, structure and photoluminescent properties of BF2 and BPh2 complexes with N,O-benzazine ligands

  摘要：

  Novel N,O-bidentate BF2 and BPh2 complexes have been prepared in good to excellent yields through coordination of 8-hydroxy-2-methylquinolines and 2-(2-hydroxyphenyl)-3H-quinazolin-4-ones with boron trifluoride etherate or triphenylborane under mild conditions. All complexes have been characterized by H-1, B-11 and F-19 NMR, mass-spectrometry and X-ray crystallography data. Some complexes have been found to exhibit a significant fluore.scence in acetonitrile solutions. Electronic and site effects of substituents in both heterocyclic and phenol fragments proved to have a profound impact on quantum yields. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.04.010

文献信息

• Vanadium-Catalyzed Synthesis of 4(3<i>H</i>)-Quinazolinones from Anthranilamides and Aryl Aldehydes
  作者：Dan Zhan、Tianbin Li、Xiaoping Zhang、Chuan Dai、Haidong Wei、Yuyu Zhang、Qingle Zeng

  DOI：10.1080/00397911.2012.717669

  日期：2013.9.17

  Abstract An efficient synthesis of 2-substituted and 2,3-disubstituted quinazolin-4(3H)-ones via tandem reaction of anthranilamides and aromatic aldehydes catalyzed by vanadyl acetylacetonate with 1 mol% loading under an air atmosphere is described. This new method is associated with several advantages such as low catalyst loading (only 1 mol%), use of green oxidant in the form of air, high atom economy

  摘要 描述了在空气气氛下，在 1 mol% 负载量的乙酰丙酮氧钒催化下，邻氨基苯甲酰胺和芳香醛的串联反应有效合成 2-取代和 2,3-二取代喹唑啉-4(3H)-酮。这种新方法具有几个优点，例如催化剂负载量低（仅 1 mol%）、使用空气形式的绿色氧化剂、高原子经济性和良好的收率。还提出了钒催化合成 4(3H)-喹唑啉酮的机理。补充材料可用于本文。访问出版商的 Synthetic Communications ® 在线版以查看免费的补充文件。图形概要
• A recyclable CuO-catalyzed synthesis of 4(3H)-quinazolinones
  作者：Dan Zhan、Tianbin Li、Haidong Wei、Wen Weng、Khashayar Ghandi、Qingle Zeng

  DOI：10.1039/c3ra41370e

  日期：——

  This paper describes the synthesis of 2-substituted and 2,3-disubstituted 4(3H)-quinazolinones via a tandem reaction involving anthranilamides and aromatic aldehydes catalyzed by 3 mol% CuO powder under air atmosphere. This new method has several advantages: it uses recyclable and cheap CuO powder as the catalyst and air as the green oxidant, water is the only byproduct, and the solvent is recycled

  本文描述了2-取代的和2,3-二取代的4-（3合成ħ）-quinazolinones经由涉及空气气氛下，通过3摩尔％的CuO粉末催化邻氨基苯甲酰胺和芳香醛的串联反应。这种新方法具有以下优点：它使用可回收且廉价的CuO粉末作为催化剂，使用空气作为绿色氧化剂，水是唯一的副产物，溶剂被回收。它易于操作，具有较高的原子经济性，并具有良好的优良收率。提出了CuO催化合成4（3 H）-喹唑啉酮的机理。
• Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones
  作者：Ting Li、Minglu Chen、Lei Yang、Zhengxin Xiong、Yongwei Wang、Fei Li、Dongyin Chen

  DOI：10.1016/j.tet.2015.12.059

  日期：2016.2

  and pyrido[2,3-d]pyrimidin-4(3H)-ones from easily available 2-halobenzamides (or 2-halonicotinamides), aldehydes, and sodium azide has been developed, which gave the corresponding target products in 50–95% yields for 29 examples. This remarkable consecutive process involved sequential copper-catalyzed SNAr, reduction, cyclization, and oxidation. Notably, this work would provide a novel synthetic strategy

  从容易获得的2-卤代苯甲酰胺（或2-卤代烟酰胺）中高效，实用地铜催化连续合成喹唑啉-4（3 H）-酮和吡啶并[2,3 - d ]嘧啶-4（3 H）-酮，已开发出醛和叠氮化钠，从而使29个实例的相应目标产物收率达到50-95％。这个非同寻常的连续过程涉及连续的铜催化的S N Ar，还原，环化和氧化。值得注意的是，这项工作将为含有喹唑啉酮类骨架的生物活性分子提供一种新颖的合成策略。