6-nitro-3-phenyl-4(3H)-quinazolinone | 964-25-0

• 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: 6-nitro-3-phenyl-4(3H)-quinazolinone
• 英文别名: 6-nitro-3-phenylquinazolin-4(3H)-one；6-nitro-3-phenyl-3H-quinazolin-4-one；3-Phenyl-6-nitro-chinazolon；6-nitro-3-phenylquinazolin-4-one
• CAS: 964-25-0
• 化学式: C₁₄H₉N₃O₃
• 分子量: 267.244
• InChiKey: MUYVFWMRDXLKLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  过氧化二异丙苯 、 2-氨基-5-硝基苯甲酰替苯胺 在 咪唑 、 copper(II) acetate monohydrate 作用下， 以 氯苯 为溶剂， 反应 10.0h， 以65%的产率得到6-nitro-3-phenyl-4(3H)-quinazolinone
  参考文献：
  名称：

  Copper-Catalyzed Radical Methylation/C–H Amination/Oxidation Cascade for the Synthesis of Quinazolinones

  摘要：

  A copper-catalyzed radical methylation/sp(3) C-H amination/oxidation reaction for the facile synthesis of quinazolinone was developed. In this cascade reaction, dicumyl peroxide acts not only as a useful oxidant but also as an efficient methyl source. Notably, a methyl radical, generated. from peroxide, was confirmed by electron paramagnetic resonance for the first time.

  DOI：

  10.1021/acs.joc.5b00191

文献信息

• TBHP as Methyl Source under Metal-Free Aerobic Conditions To Synthesize Quinazolin-4(3<i>H</i> )-ones and Quinazolines by Oxidative Amination of C(sp³ )-H Bond
  作者：Sushobhan Mukhopadhyay、Dinesh S. Barak、Sanjay Batra

  DOI：10.1002/ejoc.201800495

  日期：2018.6.15

  tert‐Butyl hydroperoxide (TBHP) served as the methyl source under metal‐free aerobic conditions in the oxidative amination of a C(sp3)–H bond to provide quinazolin‐4(3H)‐one and quinazoline derivatives.

  在无金属好氧条件下，叔丁基过氧化氢（TBHP）在C（sp 3）-H键的氧化胺化反应中作为甲基源，提供了quinazolin-4（3 H）-one和quinazoline衍生物。
• <i>N</i>,<i>N</i>-Dimethylformamide as Carbon Synthons for the Synthesis of <i>N</i>-Heterocycles: Pyrrolo/Indolo[1,2-<i>a</i>]quinoxalines and Quinazolin-4-ones
  作者：Shichen Li、Jianing Ren、Chengcheng Ding、Yishou Wang、Chen Ma

  DOI：10.1021/acs.joc.1c02067

  日期：2021.12.3

  N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered that N-methyl and

  N , N-二甲基甲酰胺 (DMF) 作为合成前体，尤其是甲基、酰基和氨基，在杂环合成和功能化中发挥了重要作用。在该协议中，通过使用不含任何金属或过氧化物的元素碘，以中等至良好的收率获得了范围广泛的 pyrrolo/indolo[1,2 - a ]quinoxalines 和 quinazolin-4-ones。我们认为DMF的N-甲基和N-酰基通过不同的机理分别参与并完成反应，这表明DMF的潜力仍有待探索。
• Eco-friendly, solvent-free novel one-pot, three-component synthesis of quinazolinones at ambient temperature catalyzed by silica gel-supported phosphomolybdic acid
  作者：Gowravaram Sabitha、N. Mallikarjuna Reddy、M. Nagendra Prasad、G. S. K. Raja、J. S. Yadav

  DOI：10.1002/jhet.361

  日期：——

  Silica gel supported Phosphomolybdic acid (PMA.SiO2) catalyzes efficiently the one‐pot three‐component coupling reaction of anthranilic acid, orthoesters, and amines at room temperature to afford 4(3H)‐Quinazolinones in high to excellent yields under solvent‐free conditions. The supported catalyst can be recovered and reused. J. Heterocyclic Chem., (2010).

  硅胶负载的磷钼酸（PMA.SiO 2）在室温下可有效催化邻氨基苯甲酸，原酸酯和胺的单锅三组分偶联反应，从而在溶剂中以高产率或优异产率得到4（3 H）-喹唑啉酮。免费条件。负载的催化剂可以回收和再利用。J.杂环化​​学。（2010）。
• Discovery of molluscicidal and cercaricidal activities of 3-substituted quinazolinone derivatives by a scaffold hopping approach using a pseudo-ring based on the intramolecular hydrogen bond formation
  作者：Wei Guo、Lv-Yin Zheng、Yong-Dong Li、Ren-Miao Wu、Qiang Chen、Ding-Qiao Yang、Xiao-Lin Fan

  DOI：10.1016/j.ejmech.2016.03.037

  日期：2016.6

  in current Schistosomiasis control. A pseudo-ring formed from salicylanilide by an intramolecular hydrogen bond led to the discovery of 3-substituted quinazolinone derivatives which showed a potent molluscicidal and cercaricidal activities.

  在目前的血吸虫病控制中，发现针对钉螺和尾c的新型拓扑剂仍然是一项重大挑战。由水杨酰苯胺通过分子内氢键形成的假环导致发现了具有强力杀灭杀虫和杀菌作用的3-取代的喹唑啉酮衍生物。
• ANWAR M., REV. ROUM. CHIM., 1981, 26, NO 4, 639-645
  作者：ANWAR M.

  DOI：——

  日期：——