2,4-bis(4-chlorophenyl)quinazoline | 1520087-48-2

• 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-bis(4-chlorophenyl)quinazoline
• 英文别名: 2,4-Bis(4-chlorophenyl)quinazoline
• CAS: 1520087-48-2
• 化学式: C₂₀H₁₂Cl₂N₂
• 分子量: 351.235
• InChiKey: KVWQGFXHMRSRHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-chlorophenyl)-4(3H)-quinazolinone 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-bis(4-chlorophenyl)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

• Four-component quinazoline synthesis from simple anilines, aromatic aldehydes and ammonium iodide under metal-free conditions
  作者：Jinjin Chen、Dan Chang、Fuhong Xiao、Guo-Jun Deng

  DOI：10.1039/c8gc02654h

  日期：——

  A four-component procedure for the preparation of substituted quinazolines from anilines, aromatic aldehydes and ammonium iodide is described. The C–H bond ortho to the amino group in anilines was directly functionalized under metal-free conditions. Two aldehydes were involved in this reaction and ammonium iodide was used as one of the nitrogen sources. This reaction provides a strategy for the facile

  描述了一种由苯胺，芳族醛和碘化铵制备取代的喹唑啉的四组分方法。的C-H键的邻位中的苯胺的氨基不含金属的条件下直接官能化。该反应涉及两种醛，碘化铵用作氮源之一。该反应提供了从简单的苯胺和其他容易获得的反应物容易地构建取代的喹唑啉的策略。
• Visible-Light-Induced Benzylic C-H Functionalization for the Synthesis of 2-Arylquinazolines
  作者：Jingchang Zhang、Qibao Wang、Yongen Guo、Lin Ding、Maocai Yan、Yinglin Gu、Jiajia Shi

  DOI：10.1002/ejoc.201900996

  日期：2019.9.15

  Visible‐light‐induced synthesis of substituted quinazolines using1‐(2‐aminoaryl)ethan‐1‐ones in conjunction with arylmethanamines as starting materials.

  可见光诱导的取代喹唑啉的合成，使用1-（2-氨基芳基）乙-1-芳基与芳基甲胺作为起始原料。
• 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。
• Csp²-O and C-C Bond Formation via Pd-Catalyzed Coupling Reaction of 2,4-Dichloroquinazoline
  作者：Alka Sharma、Vijay Luxami、Kamaldeep Paul

  DOI：10.1002/jhet.2330

  日期：2016.1

  An efficient palladium‐catalyzed C–O and subsequent C–C bond formation of 2,4‐dichloroquinazoline have been described. The designed strategy results in the synthesis of novel 2‐arylated quinazolin‐4‐ones framework with various aryl/heteroaryl boronic acids in moderate to good yields along with 2,4‐diarylated quinazolines. This methodology offers a direct transformation of aryl halides to aryl alcohols/ketone

  已经描述了有效的钯催化的C–O和随后的2,4–二氯喹唑啉的C–C键形成。该设计策略可合成具有中等至良好收率的各种芳基/杂芳基硼酸和2,4-二芳基喹唑啉的新型2-芳基喹唑啉-4-酮骨架。该方法可以将芳基卤化物直接转化为芳基醇/酮，并且可以直接应用以生成各种单芳基和二芳基喹唑啉。
• 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.