2,3-dihydro-3-(4-hydroxyphenyl)-2-(4-methylphenyl)quinazolin-4(1H)-one | 1264686-61-4

• 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-dihydro-3-(4-hydroxyphenyl)-2-(4-methylphenyl)quinazolin-4(1H)-one
• 英文别名: 3-(4-Hydroxyphenyl)-2-(4-methylphenyl)-1,2-dihydroquinazolin-4-one；3-(4-hydroxyphenyl)-2-(4-methylphenyl)-1,2-dihydroquinazolin-4-one
• CAS: 1264686-61-4
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: ZEWIWFLTYSLDEV-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：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红酸酐 、 对甲基苯甲醛 、 对氨基苯酚 在 zinc oxide nanotubes modified by SiO₂ 作用下， 反应 0.05h， 以82%的产率得到2,3-dihydro-3-(4-hydroxyphenyl)-2-(4-methylphenyl)quinazolin-4(1H)-one
  参考文献：
  名称：

  The Synthesis of 2,3-Dihydroquinazolin-4(1h)-Ones using Zinc Oxide Nanotubes Modified by Sio2 as A Catalyst with Recyclable Effect

  摘要：

  氧化锌纳米管近年来备受关注。直接使用经二氧化硅修饰的氧化锌纳米管作为可回收的催化剂，已在多个有机反应中得到应用。氧化锌催化剂的平均粒径为 57 nm，并通过 XRD 进行了表征。纳米管表面具有高密度缺陷。在少量由二氧化硅修饰的氧化锌纳米管作为催化剂存在的情况下，异酸酐和暴露于醋酸铵的芳香醛的缩合是一种简单、适用和高效的喹唑啉衍生物合成方法，其积极的方面是催化剂的可回收能力。显然，催化剂的一些特性，如经二氧化硅修饰的氧化锌纳米管的小粒径和高密度表面缺陷的结合，是催化剂具有独特催化活性的根本原因。该方法简单实用，能在温和条件下短时间内获得无与伦比的 2,3-二氢喹唑啉-4(1H)-酮衍生物。

  DOI：

  10.13005/ojc/340109

文献信息

• Synthesis of pyrazol-quinazolinones and 2,3-dihydroquinazolin-4(1H)-ones using CoAl2O4 nanoparticles as heterogeneous catalyst
  作者：Fatemeh Ahmadian、Alireza Barmak、Esmali Ghaderi、Masoumeh Bavadi、Hossein Raanaei、Khodabakhsh Niknam

  DOI：10.1007/s13738-019-01729-9

  日期：2019.12

  AbstractThe preparation and characterization of cobalt aluminate (CoAl2O4) magnetic nanoparticles and its application as a catalyst for the synthesis of a novel class of pyrazol-quinazolinones and 2,3-dihydroquinazolin-4(1H)-ones is described. The structure of the catalyst was studied by Fourier transform infrared spectroscopy, transmission electron microscopy, X-ray diffraction, and vibrating sample

  摘要描述了铝酸钴（CoAl 2 O 4）磁性纳米颗粒的制备，表征及其在合成新型吡唑-喹唑啉酮和2,3-二氢喹唑啉-4（1H）-ones催化剂中的应用。通过傅里叶变换红外光谱，透射电子显微镜，X射线衍射和振动样品磁力计分析研究了催化剂的结构。所得的铝酸钴（CoAl 2 O 4）是有效的催化剂，并以良好至优异的产率提供了所需的产物。而且，该催化剂可以容易地通过磁分离回收并循环四次而不会显着损失其催化活性。 图形摘要以CoAl 2 O 4为纳米颗粒非均相催化剂，在乙醇回流条件下，通过等规酸酐，芳族醛和胺的一锅缩合反应，合成了2,3-二氢喹唑啉-4（1H）-和一类新型的吡唑-喹唑啉酮。
• Application of the ultrasound in the mild synthesis of substituted 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heterogeneous metal–MWCNTs nanocomposites
  作者：Javad Safari、Soheila Gandomi-Ravandi

  DOI：10.1016/j.molstruc.2014.05.002

  日期：2014.8

  Abstract A practical method were applied successfully to synthesize mono- and disubstituted dihydroquinazolinones through three-component condensation of isatoic anhydride, primary amines or ammonium acetate with aromatic aldehydes in the presence of some transition metals–multi-walled carbon nanotubes under sonication. Also, metals supported on MWCNTs showed excellent catalytic performance for above-mentioned

  摘要 在一些过渡金属-多壁碳纳米管的超声作用下，通过靛红酸酐、伯胺或乙酸铵与芳香醛的三组分缩合，成功地应用了一种实用的方法来合成单和二取代的二氢喹唑啉酮。此外，负载在多壁碳纳米管上的金属对上述缩合表现出优异的催化性能。该方法提供了通用、简单和有效的方法，以优异的产率在超声处理下使用上述纳米复合材料作为催化剂提供相应的芳基取代喹唑啉酮衍生物。本协议的优点是反应方便、后处理简单、绿色环保、能源效率高、催化剂可重复使用以及反应条件温和。
• Silica-bonded S-sulfonic Acid as a Recyclable Catalyst for Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
  作者：Khodabakhsh Niknam、Mohammad Reza Mohammadizadeh、Salimeh Mirzaee

  DOI：10.1002/cjoc.201180261

  日期：2011.7

  2,3‐Dihydroquinazolin‐4(1H)‐one derivatives were synthesized via a one‐pot, three component reaction of isatoic anhydride and an aromatic aldehyde with ammonium acetate or primary amine catalyzed by silica‐bonded S‐sulfonic acid in ethanol at 80°C. The reaction work‐up is simple and the catalyst is easily separated from the products by filtration. The heterogeneous catalyst was recycled for ten runs

  2,3-二氢喹唑啉-4（1 H）-一衍生物是通过乙二酸酐和芳族醛与乙酸铵或伯胺的一锅三组分反应合成的，该乙酸铵或伯胺是在乙醇中于硅胶上键合的S-磺酸所催化的。 80℃。反应后处理很简单，催化剂很容易通过过滤从产物中分离出来。在异戊酸酐和4-氯苯甲醛与乙酸铵的缩合反应下，将多相催化剂循环使用十次，而不会失去其催化活性。
• Microwave-accelerated three components cyclocondensation in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones promoted by Cu-CNTs
  作者：Javad Safari、Soheila Gandomi-Ravandi

  DOI：10.1016/j.molcata.2013.01.031

  日期：2013.5

  Cu-CNTs efficiently catalyzes condensation reaction of isatoic anhydride, aldehydes, and primary amines or ammonium acetate to afford the corresponding 2,3-dihydroquinazolin-4(1H)-one derivatives successfully in high yield. The protocol proves to be efficient and environmentally benign in terms of very easy work-up, high yields, and ease of recovery of catalyst. In addition, the present method is superior in terms of green media, the amount of catalyst and reaction time. (C) 2013 Elsevier B.V. All rights reserved.
• The Synthesis of 2,3-Dihydroquinazolin-4(1h)-Ones using Zinc Oxide Nanotubes Modified by Sio2 as A Catalyst with Recyclable Effect
  作者：Rakhshan Hakimelahi、Mohammad H. Mousazadeh

  DOI：10.13005/ojc/340109

  日期：2018.2.28

  zinc oxid nano tubes have attracted much attention in recent years. Hardly, direct uses of zinc oxid nano tubes which modified by SiO2 as a catalyst with recyclability has been applied for several organic reactions. The average particle size of ZnO catalysts is 57 nm, it has been characterized by XRD. Nano tubes surfaces have high density defects. The condensation of isatoic anhydride and an aromatic aldehyde exposed to ammonium acetate in the presence of few amounts of zinc oxid nano tubes modified by SiO2 as a catalyst can be a simple, suitable and efficient method for the quinazolin derivatives synthesis, the positive aspect is recyclable ability of the catalyst. It is clear that some characterization of catalyst such as combination of the small particle size and high-density surface defects of zinc oxid nano tubes which modified by SiO2 is the basic reason for unique catalytic activity of the catalyst. The practical and simple method led to unbeatable yields of the 2,3-Di hydro quinazolin-4(1H)-one derivatives at short times under mild conditions.

  氧化锌纳米管近年来备受关注。直接使用经二氧化硅修饰的氧化锌纳米管作为可回收的催化剂，已在多个有机反应中得到应用。氧化锌催化剂的平均粒径为 57 nm，并通过 XRD 进行了表征。纳米管表面具有高密度缺陷。在少量由二氧化硅修饰的氧化锌纳米管作为催化剂存在的情况下，异酸酐和暴露于醋酸铵的芳香醛的缩合是一种简单、适用和高效的喹唑啉衍生物合成方法，其积极的方面是催化剂的可回收能力。显然，催化剂的一些特性，如经二氧化硅修饰的氧化锌纳米管的小粒径和高密度表面缺陷的结合，是催化剂具有独特催化活性的根本原因。该方法简单实用，能在温和条件下短时间内获得无与伦比的 2,3-二氢喹唑啉-4(1H)-酮衍生物。