2-(4-methoxyphenyl)-4-(p-tolyl)quinazoline | 1520087-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(4-methoxyphenyl)-4-(p-tolyl)quinazoline
• 英文别名: 2-(4-Methoxyphenyl)-4-(4-methylphenyl)quinazoline；2-(4-methoxyphenyl)-4-(4-methylphenyl)quinazoline
• CAS: 1520087-41-5
• 化学式: C₂₂H₁₈N₂O
• 分子量: 326.398
• InChiKey: YGANZQZLMJUVBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-4-(p-tolyl)quinazoline 在 N-碘代丁二酰亚胺 、 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  One-pot regioselective C–H activation iodination–cyanation of 2,4-diarylquinazolines using malononitrile as a cyano source

  摘要：

  已开发出一种使用NIS和马来酸二腈进行2,4-芳基喹唑啉的一锅法腈化反应。

  DOI：

  10.1039/c9ra02979f
• 作为产物：
  描述：

  2-(4-甲氧基苯基)-1H-喹唑啉-4-酮 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 2-(4-methoxyphenyl)-4-(p-tolyl)quinazoline
  参考文献：
  名称：

  Synthesis of 4-Arylquinazolines by Arylation of Quinazolin-4-ones under Mild Conditions

  摘要：

  An efficient route to 4-arylquinazolines via arylation of quinazolin-4-ones under mild condition is described. The reaction is carried out by the palladium-catalyzed coupling of quinazolin-4-ones with arylboronic acids in the presence of TsCl leading to 4-arylquinazolines in good to excellent yields.

  DOI：

  10.1055/s-0033-1339848

文献信息

• Rh(III)-catalyzed oxidative <i>ortho</i>-C–H alkylation of 2,4-diarylquinazoline with potassium alkyltrifluoroborates
  作者：Wei Gao、Chun Gong、Qin Yang、Jianjun Yuan、Linchu Xu、Yiyuan Peng

  DOI：10.1139/cjc-2017-0258

  日期：2017.10

  Alkyltrifluoroborates were used for Rh(III)-catalyzed ortho-alkylation of 2,4-disubstituted quinazoline via C–H bond activation. The reaction proceeded well with a broad substrate scope, providing a direct way to access high functional quinazoline core structure derivatives in yields up to 95%.

  烷基三氟硼酸盐用于通过 C-H 键活化对 2,4-二取代喹唑啉进行 Rh(III) 催化的邻位烷基化。该反应在广泛的底物范围内进行得很好，提供了一种以高达 95% 的产率获得高功能喹唑啉核心结构衍生物的直接方法。
• Palladium-Catalyzed and Quinazoline-Directed C–H Selective Acetoxylation of 2-Arylquinazolines
  作者：Yiyuan Peng、Song Wei、Banlai Ouyang、Zhihong Deng、Qin Yang

  DOI：10.1055/s-0037-1611908

  日期：2019.10

  successfully synthesized via the Pd-catalyzed and quinazoline-directed C–H activation/acetoxylation of the corresponding 2-arylquinazolines with iodobenzene diacetate in AcOH/Ac2O. A series of acetoxylated 2-arylquinazolines have been successfully synthesized via the Pd-catalyzed and quinazoline-directed C–H activation/acetoxylation of the corresponding 2-arylquinazolines with iodobenzene diacetate in AcOH/Ac2O

  抽象的 通过在相应的2-芳基喹唑啉在AcOH / Ac 2 O中用碘代苯二乙酸酯进行Pd催化和喹唑啉定向的CH活化/乙酰氧基化，已成功合成了一系列乙酰氧基化的2-芳基喹唑啉。 通过在相应的2-芳基喹唑啉在AcOH / Ac 2 O中用碘代苯二乙酸酯进行Pd催化和喹唑啉定向的CH活化/乙酰氧基化，已成功合成了一系列乙酰氧基化的2-芳基喹唑啉。
• Design, Synthesis and Molecular Properties Prediction of Novel Quinazoline Derivatives as Potent Antibacterial Agents
  作者：S.V. Eswararao、V. Venkataramireddy、M. Srinivasareddy、Pramod Kumar

  DOI：10.14233/ajchem.2017.20513

  日期：——

  A novel series of compounds were synthesized by C-C bond formation of substituted quinazolinones (1) with substituted boronic acids (2) to get 2,4-disubstituted quinazoline (3a-3n) in good to excellent yields. The structures of the new compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectral data. An antibacterial and antifungal activity screening results showed that compounds 3b, 3e, 3i and 3l possess excellent activity against Gram (+), Gram (-) bacteria (S. aureus, Klebsiella species, P. aeruginosa) compared to standard drugs. 3l, 3g and 3n showed better antifungal activity against A. nigeri and C. albicans organisms. In this investigation, the target compounds 3a-3n were subjected to in silico molecular properties prediction and drug likeness by employing Molinspiration (Molinspiration, 2014) and MolSoft (MolSoft, 2007) property explorer tool kits for predicting their high oral bioavailability.

  通过取代的硼酸（2）与取代的喹唑啉酮（1）形成 C-C 键，合成了一系列新型化合物，得到了 2,4-二取代的喹唑啉（3a-3n），收率良好至极佳。红外光谱、1H NMR、13C NMR 和质谱数据证实了这些新化合物的结构。抗菌和抗真菌活性筛选结果表明，与标准药物相比，化合物 3b、3e、3i 和 3l 对革兰氏（+）和革兰氏（-）细菌（金黄色葡萄球菌、克雷伯氏菌、绿脓杆菌）具有极佳的活性。3l、3g 和 3n 对 A. nigeri 和 C. albicans 微生物具有更好的抗真菌活性。在这项研究中，利用 Molinspiration（Molinspiration，2014 年）和 MolSoft（MolSoft，2007 年）性质探索工具包对目标化合物 3a-3n 进行了分子性质和药物相似性的硅学预测，以预测其较高的口服生物利用度。
• One-pot regioselective C–H activation iodination–cyanation of 2,4-diarylquinazolines using malononitrile as a cyano source
  作者：Ziqiao Yan、Banlai Ouyang、Xunchun Mao、Wei Gao、Zhihong Deng、Yiyuan Peng

  DOI：10.1039/c9ra02979f

  日期：——

  A one-pot cyanation of 2,4-arylquinazoline with NIS and malononitrile has been developed.

  已开发出一种使用NIS和马来酸二腈进行2,4-芳基喹唑啉的一锅法腈化反应。
• Synthesis of 4-Arylquinazolines by Arylation of Quinazolin-4-ones under Mild Conditions
  作者：Yiyuan Peng、Guanyinsheng Qiu、Ping Huang、Qin Yang、Hui Lu、Jingshi Xu、Zhihong Deng、Ming Zhang

  DOI：10.1055/s-0033-1339848

  日期：——

  An efficient route to 4-arylquinazolines via arylation of quinazolin-4-ones under mild condition is described. The reaction is carried out by the palladium-catalyzed coupling of quinazolin-4-ones with arylboronic acids in the presence of TsCl leading to 4-arylquinazolines in good to excellent yields.