3-(2-chlorobenzyl)quinazolin-4(3H)-one | 82387-82-4

• 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: 3-(2-chlorobenzyl)quinazolin-4(3H)-one
• 英文别名: 3-(2-chlorobenzyl)-4(3H)-quinazolinone；3-[(2-chlorophenyl)methyl]quinazolin-4-one
• CAS: 82387-82-4
• 化学式: C₁₅H₁₁ClN₂O
• mdl: MFCD02360765
• 分子量: 270.718
• InChiKey: PYNNHXAXOXPFBE-UHFFFAOYSA-N

物化性质

• 熔点：
  112-116 °C(Solv: benzene (71-43-2))
• 沸点：
  445.9±47.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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

• 作为反应物：
  描述：

  3-(2-chlorobenzyl)quinazolin-4(3H)-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 48.0h， 以91%的产率得到3-(2-Chlorobenzyl)-1,2,3,4-tetrahydroquinazoline
  参考文献：
  名称：

  Synthe`se ete´tudein vitro de l'activite´antiagre´gante plaquettaire de de´rive´s de la te´trahydro-1,2,3,4 quinazoline

  摘要：

  DOI：

  10.1016/0223-5234(89)90058-5
• 作为产物：
  描述：

  邻氯苯甲胺 以 乙醇 为溶剂， 反应 4.0h， 生成 3-(2-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

• 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。
• A Domino Process for the Sustainable Synthesis of Quinazolin-4(3H)-ones with Direct Chemo- and Regioselective Bromination
  作者：Ehsan Sheikhi、Mehdi Adib、Rozita Yazzaf、Mehdi Jahani、Mehdi Ghavidel

  DOI：10.1055/s-0037-1610226

  日期：2018.9

  An efficient approach is reported for the direct and sustainable construction of quinazolin-4(3H)-ones through a three-component reaction of isatoic anhydride, primary amines, and bromoacetyl bromide or chloroacetyl chloride in the presence of K2CO3 in DMSO. With bromoacetyl bromide, mono- or dibrominated quinazolinone scaffolds were obtainable in a chemo- and regioselective manner.

  据报道，在 DMSO 中存在 K2CO3 的情况下，通过靛红酸酐、伯胺和溴乙酰溴或氯乙酰氯的三组分反应，直接和可持续地构建喹唑啉-4(3H)-酮的有效方法。使用溴乙酰溴，可以通过化学和区域选择性方式获得单溴化或二溴化喹唑啉酮支架。
• Copper-Catalyzed Oxidative Multicomponent Annulation Reaction for Direct Synthesis of Quinazolinones via an Imine-Protection Strategy
  作者：Yantang Liang、Zhenda Tan、Huanfeng Jiang、Zhibo Zhu、Min Zhang

  DOI：10.1021/acs.orglett.9b01608

  日期：2019.6.21

  Via an imine-protection strategy, we herein present an unprecedented copper-catalyzed oxidative multicomponent annulation reaction for direct synthesis of quinazolinones. The construction of various products is achieved via formation of three C–N and one C–C bonds in conjunction with the benzylic functionalization. The merits of easily available feedstocks, naturally abundant catalyst, good functional

  通过亚胺保护策略，我们在这里提出了一种空前的铜催化的氧化多组分环合反应，用于直接合成喹唑啉酮。通过形成三个C–N和一个C–C键以及苄基官能团，可以实现各种产物的构建。易于获得的原料，天然丰富的催化剂，良好的官能团和底物相容性以及作为副产物释放H 2 O的优点，使已开发的化学方法成为获取喹唑啉酮的实用方法。
• 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。
• tert-Butyl Hydroperoxide Promoted the Reaction of Quinazoline-3-oxides with Primary Amines Affording Quinazolin-4(3<i>H</i>)-ones
  作者：Jin Luo、Juelin Wan、Lianlian Wu、Lingyun Yang、Tao Wang

  DOI：10.1021/acs.joc.2c00898

  日期：2022.8.5

  synthesis of quinazolin-4(3H)-ones via the reaction of quinazoline-3-oxides with primary amines is described. This approach is demonstrated to be applicable for a broad range of substrates and proceeds efficiently under metal-free and mild reaction conditions employing easily available tert-butyl hydroperoxide as the oxidant. Remarkably, 3-(2-(1H-indol-3-yl) ethyl)quinazolin-4(3H)-one 3w, which was conveniently

  介绍了一种通过 quinazolin-3-氧化物与伯胺反应合成 quinazolin-4(3 H )-ones 的有效且简便的方法。这种方法被证明适用于广泛的底物，并且在使用容易获得的叔丁基过氧化氢作为氧化剂的无金属和温和的反应条件下有效地进行。值得注意的是，3-(2-(1 H -indol-3-yl) ethyl)quinazolin-4(3 H )-one 3w是通过该方法方便地以 70% 的收率获得的，是合成生物活性吴茱萸碱和鲁坦平。