7-chloro-2-(4-methoxyphenyl)quinazolin-4(3H)-one | 19407-66-0

• 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: 7-chloro-2-(4-methoxyphenyl)quinazolin-4(3H)-one
• 英文别名: 7-chloro-2-(4-methoxyphenyl)-3H-quinazolin-4-one
• CAS: 19407-66-0
• 化学式: C₁₅H₁₁ClN₂O₂
• 分子量: 286.718
• InChiKey: AJRIBEMRALIVAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 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：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基2-胺-4-氯苯酚酯 在 吡啶 、 copper(I) 2-hydroxy-3-methylbenzoate 、 氨 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 、 水 、 甲苯 为溶剂， -34.0~20.0 ℃ 、200.0 kPa 条件下， 反应 58.84h， 生成 7-chloro-2-(4-methoxyphenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Conversion of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones to N(3)-Unsubstituted 2-(Het)Arylquinazolin-4(3H)-ones by Copper-Mediated Pd-Catalysed Cross-Coupling Reactions

  摘要：

  With the purpose of searching for new heterocyclic building blocks, a new method to access N(3)-unsubstituted 2-(het)arylquinazolin-4(3H)-ones from 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives was developed. The synthetic protocol was based on the copper-mediated palladium-catalysed cross-coupling reactions of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones with (het)arylstannanes or their S-benzylated derivatives with (het)arylboronic acids, using CuBr center dot Me2S and CuMeSal as promoters, respectively. A similar transformation was applied for the preparation of 2-aryl[ 1]benzothieno[3,2-d]pyrimidin-4(3H)-ones.

  DOI：

  10.3987/com-15-s(t)12

文献信息

• Computer-Aided Design, Synthesis and Validation of 2-Phenylquinazolinone Fragments as CDK9 Inhibitors with Anti-HIV-1 Tat-Mediated Transcription Activity
  作者：Luca Sancineto、Nunzio Iraci、Serena Massari、Vanessa Attanasio、Gianmarco Corazza、Maria Letizia Barreca、Stefano Sabatini、Giuseppe Manfroni、Nilla Roberta Avanzi、Violetta Cecchetti、Christophe Pannecouque、Alessandro Marcello、Oriana Tabarrini

  DOI：10.1002/cmdc.201300287

  日期：2013.12

  The activity of the cyclin‐dependent kinase 9 (CDK9) is critical for HIV‐1 Tat‐mediated transcription and represents a promising target for antiviral therapy. Here we present computational studies that, along with preliminary synthetic efforts, allowed us to identify and characterize a new class of nontoxic anti‐CDK9 chemotypes based on the 2‐phenylquinazolinone scaffold. Inhibition of CDK9 translated

  细胞周期蛋白依赖性激酶9（CDK9）的活性对于HIV-1 Tat介导的转录至关重要，是抗病毒治疗的有希望的靶标。在这里，我们介绍了计算研究，以及初步的合成努力，使我们能够鉴定和表征基于2-苯基喹唑啉酮骨架的新型无毒抗CDK9化学型。对CDK9的抑制转化为选择性干扰Tat介导的病毒启动子反式激活的能力以及对潜伏感染细胞中HIV-1激活的抑制的能力，其中最有效的衍生物37（2-（4-氨基苯基）-7-氯喹唑啉-4（3 H ^） -酮）示出IC 50为4.0μ值中号。由于本文报道的2-苯基喹唑啉酮仅仅是片段，因此它们在很大程度上是可优化的，从而为开发具有更高效能的衍生物铺平了道路。
• [DDQM][HSO₄]/TBHP as a Multifunctional Catalyst for the Metal Free Tandem Oxidative Synthesis of 2-Phenylquinazolin-4(3<i>H</i>)-ones
  作者：Bidyutjyoti Dutta、Nilakshi Dutta、Apurba Dutta、Montu Gogoi、Sanjay Mehra、Arvind Kumar、Kalyanjyoti Deori、Diganta Sarma

  DOI：10.1021/acs.joc.2c00908

  日期：——

  in 3.5 min incorporating microwave irradiation. Photochemically the reaction proceeds for 4 h at room temperature and thermally for 8 h at 120 °C. Further IL-assisted metal, solvent, and base free in situ oxidation of benzyl alcohols to aldehydes shows its task specificity. The multifunctionality of the IL was reestablished with the synthesis of two Wnt pathway antagonists.

  设计并探索了一种双功能离子液体（IL）[DDQM][HSO 4 ]作为三效催化剂，用于在 3.5 分钟内结合微波从邻氨基苯甲酰胺和苯甲醇合成2-苯基喹唑啉-4(3 H )-酮辐照。光化学反应在室温下进行 4 小时，热反应在 120 °C 下进行 8 小时。进一步的 IL 辅助的无金属、溶剂和碱的苯甲醇原位氧化成醛显示了其任务特异性。通过合成两种 Wnt 途径拮抗剂，重建了 IL 的多功能性。
• Room temperature ligand-free Cu₂O–H₂O₂ catalyzed tandem oxidative synthesis of quinazoline-4(3<i>H</i>)-one and quinazoline derivatives
  作者：Nilakshi Dutta、Bidyutjyoti Dutta、Apurba Dutta、Bipul Sarma、Diganta Sarma

  DOI：10.1039/d2ob02085h

  日期：——

  2-substituted quinazoline-4(3H)-ones from 2-aminobenzonitrile and benzyl alcohol derivatives and additionally 2-substituted quinazolines from 2-aminobenzylamine and benzaldehyde derivatives. Mild oxidant H2O2 was utilized, providing excellent product yields. The molecular structure of one of the compounds was substantiated through SC-XRD. The versatility of the protocol was demonstrated through gram-scale syntheses

  已开发出一种高效且简单的铜催化体系，用于从 2-氨基苯甲腈和苯甲醇衍生物合成具有药用价值的 2-取代喹唑啉-4(3 H )-化合物，以及从 2-氨基苄胺和苯甲醛衍生物合成 2-取代喹唑啉。使用温和的氧化剂 H 2 O 2，​​提供优异的产品收率。其中一种化合物的分子结构通过 SC-XRD 得到证实。通过克级合成证明了该协议的多功能性。
• 6-(and 7-)-Chloro-4-(1-diethylamino-4-pentylamino)-2-(p-methoxyphenyl)- quinazoline Dihydrochlorides
  作者：R. L. McKee、M. K. McKee、R. W. Bost

  DOI：10.1021/ja01196a063

  日期：1947.4
• One‐pot Tandem Synthesis and Spontaneous Product Separation of N‐heterocycles based on Bifunctional Small‐molecule Photocatalyst
  作者：Xin‐Rong Yao、Meng‐Ze Jia、Xiao‐Li Miao、Yun‐Rui Chen、Jia‐Qi Pan、Jie Zhang

  DOI：10.1002/cssc.202301495

  日期：2024.4.8

  Homogeneous and heterogeneous reactions wherein the resulting products remain dissolved in solvents generally require complicated separation and purification process, despite the advantage of heterogeneous systems allowing retrieval of catalysts. Herein, we have developed an efficient approach for the one‐pot tandem synthesis of quinazolines, quinazolinones and benzothiadiazine 1,1‐dioxides from alcohols and amines utilizing a bifunctional bipyridinium photocatalyst with redox and Lewis acid sites using air as an oxidant. Through solvent‐modulation strategy, the photocatalytic system exhibits high performance and enables most products to separate spontaneously. Consequently, the homogeneous catalyst can be reused by direct centrifugation isolation of the products. Notably, the method is also applicable to the less active substrates, such as heterocyclic alcohols and aliphatic alcohols, and thus provides an efficient and environmentally friendly photocatalytic route with spontaneous separation of N‐heterocycles to reduce production costs and meet the needs of atomic economy and green chemistry.