3-(4-chlorobenzyl)quinazolin-4(3H)-one | 82387-83-5

• 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-(4-chlorobenzyl)quinazolin-4(3H)-one
• 英文别名: 3-[(4-chlorophenyl)methyl]quinazolin-4-one
• CAS: 82387-83-5
• 化学式: C₁₅H₁₁ClN₂O
• mdl: MFCD02170595
• 分子量: 270.718
• InChiKey: AKRYEYOAOUPPMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯苄胺 以 乙醇 为溶剂， 反应 4.0h， 生成 3-(4-chlorobenzyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Gravier; Dupin; Casadebaig, Pharmazie, 1992, vol. 47, # 2, p. 91 - 94

  摘要：

  DOI：

文献信息

• Synthesis, Anti-microbial and Molecular Docking Studies of Quinazolin-4(3H)-one Derivatives
  作者：Yahia Mabkhot、Munirah Al-Har、Assem Barakat、Fahad Aldawsari、Ali Aldalbahi、Zaheer Ul-Haq

  DOI：10.3390/molecules19078725

  日期：——

  In this work, synthesis, antimicrobial activities and molecular docking studies of some new series of substituted quinazolinone 2a–h and 3a–d were described. Starting form 2-aminobenzamide derivatives 1, a new series of quinazolinone derivatives has been synthesized, in high yields, assisted by microwave and classical methods. Some of these substituted quinazolinones were tested for their antimicrobial activity against Gram-negative bacteria (Pseudomonas aeruginosa and Esherichia coli) and Gram-positive bacteria (Staphylococcus aureus, and Bacillus subtilis), and anti-fungal activity against (Aspergillus fumigatus, Saccharomyces cervevisiae, and Candida albicans) using agar well diffusion method. Among the prepared products, 3-benzyl-2-(4-chlorophenyl)quinazolin-4(3H)-one (3a) was found to exhibits the most potent in vitro anti-microbial activity with MICs of 25.6 ± 0.5, 24.3 ± 0.4, 30.1 ± 0.6, and 25.1 ± 0.5 µg/mL against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Esherichia coli, respectively. Compound 3a was found to exhibits the most potent in vitro anti-fungal activity with MICs of 18.3 ± 0.6, 23.1 ± 0.4, and 26.1 ± 0. 5 µg/mL against Aspergillus fumigatus, Saccharomyces cervevisiae, and Candidaal bicans, respectively.

  在这项工作中，描述了一些新的取代喹唑啉酮2a–h和3a–d的合成、抗微生物活性及分子对接研究。从2-氨基苯甲酰胺衍生物1出发，通过微波辅助和经典方法，高效合成了一系列喹唑啉酮衍生物。其中一些取代喹唑啉酮通过琼脂孔扩散法测试了它们对革兰氏阴性菌（铜绿假单胞菌和大肠杆菌）和革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）以及抗真菌活性（烟曲霉、酿酒酵母和白色念珠菌）的抗微生物活性。在制备的产品中，3-苄基-2-(4-氯苯基)喹唑啉-4(3H)-酮（3a）表现出最强的体外抗微生物活性，对金黄色葡萄球菌、枯草芽孢杆菌、铜绿假单胞菌和大肠杆菌的MIC值分别为25.6 ± 0.5、24.3 ± 0.4、30.1 ± 0.6和25.1 ± 0.5 µg/mL。化合物3a还表现出最强的体外抗真菌活性，对烟曲霉、酿酒酵母和白色念珠菌的MIC值分别为18.3 ± 0.6、23.1 ± 0.4和26.1 ± 0.5 µg/mL。
• Selective Oxidative Cleavage of 3-Methylindoles with Primary Amines Affording Quinazolinones
  作者：Junhui He、Jianyu Dong、Lebin Su、Shaofeng Wu、Lixin Liu、Shuang-Feng Yin、Yongbo Zhou

  DOI：10.1021/acs.orglett.0c00271

  日期：2020.4.3

  A selective functionalization of C–C═C bonds toward N–C═O bonds is realized by an n-Bu4NI-catalyzed reaction of 3-methylindoles with primary amines using TBHP as the unique oxidant. The systematic process involves oxygenation, nitrogenation, ring-opening, and recyclization, affording a broad range of quinazolinones in good to excellent yields.

  的朝N-C = O键的C-C = C键的选择性官能化是通过实现Ñ -Bu 4 3- methylindoles使用TBHP作为唯一氧化剂伯胺NI-催化反应。系统的过程涉及氧合，硝化，开环和再循环，从而以良好或优异的收率提供了多种喹唑啉酮。
• Pd/Fe₃O₄ supported on nitrogen-doped reduced graphene oxide for room-temperature isocyanide insertion reactions
  作者：Karandeep Singh、Ajay K. Singh、Devendra Singh、Rakhi Singh、Siddharth Sharma

  DOI：10.1039/c5cy01973g

  日期：——

  graphene oxide (N-rGO) catalyst was developed to carry out the synthesis of quinazolinones and phenanthridines under extremely mild conditions through isocyanide insertion cascades. The supported Pd/Fe3O4 nanoparticles could be easily recovered from the reaction mixture and reused several times without any loss in catalytic activity.

  开发了一种多功能的Pd / Fe 3 O 4负载在N掺杂的还原氧化石墨烯（N-rGO）催化剂上，以在极温和的条件下通过异氰酸酯插入级联反应进行喹唑啉酮和菲啶的合成。负载的Pd / Fe 3 O 4纳米颗粒可以很容易地从反应混合物中回收并重复使用数次，而不会降低催化活性。
• Highly Efficient Four-Component Synthesis of 4(3<i>H</i>)-Quinazolinones: Palladium-Catalyzed Carbonylative Coupling Reactions
  作者：Lin He、Haoquan Li、Helfried Neumann、Matthias Beller、Xiao-Feng Wu

  DOI：10.1002/anie.201308756

  日期：2014.1.27

  Given the importance of quinazolinones and carbonylative transformations, a palladium‐catalyzed four‐component carbonylative coupling system for the synthesis of diverse 4(3H)‐quinazolinone in a concise and convergent fashion has been developed. Starting from 2‐bromoanilines (1 mmol), trimethyl orthoformate (2 mmol), and amines (1.1 mmol), under 10 bar of CO, the desired products were isolated in good

  考虑到喹唑啉酮和羰基化转化的重要性，已经开发了一种钯催化的四组分羰基化偶联体系，用于以简明和收敛的方式合成各种4（3 H）-喹唑啉酮。在10 bar CO下，从2-溴苯胺（1 mmol），原甲酸三甲酯（2 mmol）和胺（1.1 mmol）开始，在Pd（OAc）2（2 mol ％），BuPAd 2（6 mol％）在1,4-二恶烷（2 mL）中在100°C下使用N，N-二异丙基乙胺（2 mmol）为碱。值得注意的是，该方法可耐受各种反应性官能团的存在，并且对喹唑啉酮类具有非常高的选择性，并且被用于生物活性二氢芸香碱的前体的合成。
• 3-Aminoalkyl- and 3-benzyl-4(3H)-quinazolinones
  作者：František Roubínek、Josef Vavřina、Zdeněk Buděšínský

  DOI：10.1135/cccc19820630

  日期：——

  Reaction of 3-(2,3-epoxypropyl)-4(3H)-quinazolinone and/or its 6,7-dichloro- and 7-bromo-6-chloro-derivatives (Ib, Ic) with 5-diethylamino-2-pentylamine, 3-diethylaminomethyl-4-hydroxyaniline, 3,4-methylenedioxyaniline and 4-dimethylaminoaniline gave the corresponding substituted 4(3H)-quinazolinones, IIa, IIIb, IVb, Vc and VIc. Reactions of 3-(2-chloroethyl)-4(3H)-quinazolinones with the substituted anilines, pyridine and pyrrolidine gave rise to 3-(2-amino-ethyl)-4(3H)-quinazolinones VIIIa-VIIIj, IX and X. The piperidine derivative XI was obtained by the action of 1-(2-chloroethyl) piperidine on 4(3H)-quinazolinone. Reactions of 2-chlorobenzyl chloride 4-chlorobenzylchloride and 3,4,5-trimethoxybenzoyl chloride with 4(3H)-quinazolinone afforded 3-(2-chlorobenzyl)-, 3-(4-chlorobenzyl)-4(3H)-quinazolinone and 3-(3,4,5,-trimethoxybenzoyl)-4(3H)-quinazolinone (XII, XIII, XIV). All the compounds were screened for coccidiostatic and antihelmintic activity.

  3-(2,3-环氧丙基)-4(3H)-喹唑啉酮及/或其6,7-二氯和7-溴-6-氯衍生物(Ib, Ic)与5-二乙胺基-2-戊胺、3-二乙胺甲基-4-羟基苯胺、3,4-亚甲二氧基苯胺和4-二甲胺基苯胺反应，得到相应的取代4(3H)-喹唑啉酮，IIa、IIIb、IVb、Vc和VIc。3-(2-氯乙基)-4(3H)-喹唑啉酮与取代苯胺、吡啶和吡咯烷的反应产生3-(2-氨基乙基)-4(3H)-喹唑啉酮VIIIa-VIIIj、IX和X。通过1-(2-氯乙基)哌啶对4(3H)-喹唑啉酮的作用得到哌啶衍生物XI。2-氯苄基氯化物、4-氯苄基氯化物和3,4,5-三甲氧基苯甲酰氯与4(3H)-喹唑啉酮的反应得到3-(2-氯苄基)-、3-(4-氯苄基)-4(3H)-喹唑啉酮和3-(3,4,5-三甲氧基苯甲酰)-4(3H)-喹唑啉酮(XII、XIII、XIV)。所有化合物均进行了抗球虫和抗蠕虫活性筛选。