3-(4-溴苯基)-2-甲基喹唑烷-4(3h)-酮 | 1788-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-(4-溴苯基)-2-甲基喹唑烷-4(3h)-酮
• 英文名称: 3-(4-bromophenyl)-2-methylquinazolin-4(3H)-one
• 英文别名: 3-(4-bromophenyl)-2-methylquinazolin-4-one
• CAS: 1788-95-0
• 化学式: C₁₅H₁₁BrN₂O
• mdl: MFCD00437360
• 分子量: 315.169
• InChiKey: HNDXCNZDFXGBRU-UHFFFAOYSA-N

物化性质

• 熔点：
  165-167 °C
• 沸点：
  453.9±47.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(4-溴苯基)-2-甲基喹唑烷-4(3h)-酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以30%的产率得到2-Methyl-3-(4'-bromophenyl)-1,2,3,4-tetrahydroquinazolin-4-one
  参考文献：
  名称：

  Studies in the 3H-quinazol-4-one series. XI. Synthesis and properties of 3-(4′-bromophenyl)-l,2,3,4-tetrahydroquinazolin-4-ones

  摘要：

  DOI：

  10.1007/bf00770317
• 作为产物：
  描述：

  2-Methyl-3-(4'-bromophenyl)-1,2,3,4-tetrahydroquinazolin-4-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以33.3 mg的产率得到3-(4-溴苯基)-2-甲基喹唑烷-4(3h)-酮
  参考文献：
  名称：

  铜催化 2-氨基苯甲酰胺与叔胺串联反应合成喹唑啉酮衍生物

  摘要：

  我们开发了铜催化的 2-氨基苯甲酰胺与叔胺的串联反应，用于形成喹唑啉酮衍生物。该策略包括在一锅中进行的两个步骤（环化和偶联）。许多底物在标准条件下反应良好，以中等至良好的产率得到相应的喹唑啉酮衍生物。

  DOI：

  10.1055/s-0036-1588881

文献信息

• Palladium-catalyzed four-component carbonylative synthesis of 2,3-disubstituted quinazolin-4(3H)-ones: Convenient methaqualone preparation
  作者：Jin-Bao Peng、Hui-Qing Geng、Wei Wang、Xinxin Qi、Jun Ying、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2018.06.007

  日期：2018.9

  A palladium-catalyzed four-component carbonylative cyclization reaction for the synthesis of 2,3-disubstituted quinazolin-4(3H)-ones has been developed. A range of different 2,3-disubstituted quinazolin-4(3H)-one derivatives were prepared in moderate to good yields employing simple and readily accessible 2-iodoanilines, nitro compounds and acid anhydrides as the synthetic precursors. Mo(CO)6 acted

  已经开发了钯催化的四组分羰基环化反应，用于合成2,3-二取代的喹唑啉-4（3H）-one。使用简单且易于获得的2-碘苯胺，硝基化合物和酸酐作为合成前体，以中等至良好的产率制备了一系列不同的2,3-二取代的喹唑啉-4（3H）-one衍生物。Mo（CO）6既充当固体CO源又充当还原剂。值得注意的是，在我们的条件下，甲喹酮作为镇静剂和催眠药也可以很容易地制备，收率为68％（4b）。
• Synthesis, biological evaluation and structure–activity relationship of 2-styrylquinazolones as anti-tubercular agents
  作者：Pradeep S. Jadhavar、Tejas M. Dhameliya、Maulikkumar D. Vaja、Dinesh Kumar、Jonnalagadda Padma Sridevi、Perumal Yogeeswari、Dharmarajan Sriram、Asit K. Chakraborti

  DOI：10.1016/j.bmcl.2016.04.012

  日期：2016.6

  2-Styrylquinazolones are reported as a novel class of potent anti-mycobacterial agents. Forty-six target compounds have been synthesized using one pot reaction involving isatoic anhydride, amine, and triethyl orthoacetate followed by aldehyde to construct the 2-styrylquinazolone scaffold. The anti-mycobacterial potency of the compounds was determined against H37Rv strain. Twenty-six compounds exhibited

  据报道2-苯乙烯基喹唑啉酮是一类新型的有效的抗分枝杆菌药。使用一锅反应合成了46种目标化合物，该反应包括等角酸酐，胺和原乙酸三乙酯，然后通过醛来构建2-苯乙烯基喹唑酮骨架。测定了化合物对H 37 Rv株的抗分枝杆菌效力。26种化合物的抗Mtb活性在0.40–6.25μg/ mL的范围内。三种化合物8c，8d和8ab的MIC均为0.78μg/ mL，并且对治疗指数> 64的HEK 293T细胞系无毒（在50μg/ mL处抑制<50％）。最有效的化合物8ar显示MIC为0.40μg/ mL，治疗指数> 125。已经建立了这类化合物的早期结构活性关系。计算研究表明这些化合物与青霉素结合蛋白（PBPs）结合的可能性。
• Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: applications towards the synthesis of drugs
  作者：Dinesh Kumar、Pradeep S. Jadhavar、Manesh Nautiyal、Himanshu Sharma、Prahlad K. Meena、Legesse Adane、Sahaj Pancholia、Asit K. Chakraborti

  DOI：10.1039/c5ra03888j

  日期：——

  Simple, convenient, and green synthetic protocols have been developed for the one pot synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones under catalyst and solvent free conditions.

  已开发出简单、方便且绿色的合成方案，用于在无催化剂和溶剂的条件下一锅法合成2,3-二取代喹唑啉-4(3H)-酮和2-苯乙烯基-3-取代喹唑啉-4(3H)-酮。
• Expeditious Synthesis and Spectroscopic Characterization of 2-Methyl-3-substituted-quinazolin-4(3H)-one Derivatives
  作者：OLAYINKA O. AJANI、OLUWATOSIN Y. AUDU、MARKUS W. GERMANN、BABATUNDE L. BELLO

  DOI：10.13005/ojc/330203

  日期：2017.4.28

  Quinazoline and quinazolinone derivatives are well-known bioactive heterocycles owing to their therapeutic diversity and extensive medicinal application in drug design and pharmaceutics. A series of 2-methyl-3-substituted quinazolin-4(3H)-one derivatives 8a-q was herein synthesized from synthetic conversion of anthranilic acid to 2-methyl-4H-3,1-benzoxazi-4-one, 7 which was subsequently transformed to the targeted 2,3-disubstituted quinazolin-4(3H)-one derivatives 8a-q by reacting with some notable amino-containing moieties via an ameliorable pathway. The catalyst-free synthesis was successful achieved by careful reaction optimization study using solvent choice and reaction temperature variability as key parameters. The chemical structures of the synthesized compounds were confirmed by IR, UV, 1H-NMR, 13C-NMR and DEPT-135 as well as analytical data.

  喹唉及其衍生物是一类因其治疗多样性和在药物设计和制药中的广泛应用而著名的生物活性杂环化合物。本研究通过将邻氨基苯甲酸转化为2-甲基-4H-3,1-苯并恶嗪-4-酮7，进而与一系列含有氨基的基团反应，合成了一系列2-甲基-3-取代喹唑啉-4(3H)-酮衍生物8a-q。通过选择溶剂和反应温度作为关键参数的精细反应优化研究，实现了无催化剂的合成路线。合成的化合物的化学结构通过IR、UV、1H-NMR、13C-NMR、DEPT-135以及分析数据进行了确认。
• Screening of Natural Deep Eutectic Solvents for Green Synthesis of 2-methyl-3-substituted Quinazolinones and Microwave-Assisted Synthesis of 3-aryl Quinazolinones in Ethanol
  作者：Mario Komar、Maja Molnar、Anastazija Konjarević

  DOI：10.5562/cca3597

  日期：——

  In this study, two fast and efficient protocols for green synthesis of 3-substituted quinazolinones were perfomed. A synthesis of 2-methyl-3-substituted quinazolinones was performed in natural deep eutectic solvents, while 3-aryl quinazolinones were obtained by using microwave assisted synthesis. Benzoxazinone, which was used as an intermediate in the synthesis of 2-methyl-3-substituted quinazolinones, was prepared conventionally from anthranilic acid and acetic anhydride. In order to find the most appropriate synthetic path, twenty natural deep eutectic solvents were applied as a solvent in these syntheses. Choline chloride:urea (1 : 2) was found to be the most efficient solvent and was further used in the synthesis of 2-methyl quinazolinone derivatives (2–12). 3-Aryl quinazolinones (13–17), on the other hand, were synthesized in one-pot microwave-assisted reaction of anthranilic acid, different amines and trimethyl orthoformate. All compounds were synthesized in good to excellent yields, characterized by LC-MS/MS spectrometry and 1H- and 13C-NMR spectroscopy.

  本研究采用两种快速高效的方法绿色合成 3-取代喹唑啉酮。在天然深共晶溶剂中合成了 2-甲基-3-取代喹唑啉酮，而通过微波辅助合成获得了 3-芳基喹唑啉酮。合成 2-甲基-3-取代喹唑啉酮的中间体苯并噁嗪酮是用蚁酸和乙酸酐通过传统方法制备的。为了找到最合适的合成途径，在这些合成中使用了 20 种天然深共晶溶剂作为溶剂。结果发现氯化胆碱：脲（1:2）是最有效的溶剂，并被进一步用于合成 2-甲基喹唑啉酮衍生物 (2-12)。另一方面，3-芳基喹唑啉酮（13-17）是在蚁酸、不同的胺和原甲酸三甲酯的微波辅助反应中一锅合成的。所有化合物均以良好至极佳的收率合成，并通过 LC-MS/MS 光谱法以及 1H 和 13C-NMR 光谱法进行了表征。