2-(4-chlorophenyl)-4-(p-tolyl)quinazoline | 1520087-46-0

• 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-chlorophenyl)-4-(p-tolyl)quinazoline
• 英文别名: 2-(4-Chlorophenyl)-4-(p-tolyl)quinazoline；2-(4-chlorophenyl)-4-(4-methylphenyl)quinazoline
• CAS: 1520087-46-0
• 化学式: C₂₁H₁₅ClN₂
• 分子量: 330.816
• InChiKey: RWSYZMHMAUUFAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-4-(p-tolyl)quinazoline 在 copper(I) oxide 、 potassium fluoride 、 N-碘代丁二酰亚胺 、 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 2,9-二甲基-4,7二苯基-1,10-菲啰啉 、 potassium tert-butylate 作用下， 以 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 2-(2,6-dicyano-4-chlorophenyl)-4-(p-tolyl)quinazoline
  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-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-chlorophenyl)-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

• Ru(II)-Catalyzed C–H Activation and Annulation Reaction via Carbon–Carbon Triple Bond Cleavage
  作者：Rashmi Prakash、Bidisha R. Bora、Romesh C. Boruah、Sanjib Gogoi

  DOI：10.1021/acs.orglett.8b00643

  日期：2018.4.20

  An unprecedented Ru(II)-catalyzed C–H activation and annulation reaction, which proceeds via C–C triple bond cleavage, is reported. This reaction of 2-phenyldihydrophthalazinediones with alkynes, which works most efficiently in the presence of bidented ligand 1,3-bis(diphenylphosphino)propane, affords good yields of substituted quinazolines.

  据报道，空前的Ru（II）催化的CH活化和环化反应是通过CC的三键裂解而进行的。2-苯基二氢酞嗪二酮与炔烃的这种反应在双键配体1,3-双（二苯基膦基）丙烷的存在下最有效地进行，产生了高产率的取代喹唑啉。
• 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。
• Quinazoline-directed regioselective arylation via palladium catalysis: synthesis of 2-(1-biaryl)-4-arylquinazolines
  作者：Yiyuan Peng、Mengjing Zeng、Hongmin Wang、Jia Zhu、Qin Yang、Zhihong Deng、Cuiyi Yu

  DOI：10.1016/j.tet.2015.10.042

  日期：2015.12

  Quinazoline was used as a directing group for palladium-catalyzed ortho-mono-arylation of 2,4-disubstituted quinazoline via C–H bond activation. The reaction proceeded well with a broad substrate scope in a highly regioselective manner to provide a direct way to access highly functional quinazoline core structure derivatives.

  喹唑啉被用作通过CH键活化钯催化2,4-二取代喹唑啉的邻单芳基化的指导基团。该反应以高度区域选择性的方式在广泛的底物范围内进行得很好，从而提供了直接途径来获得功能性强的喹唑啉核心结构衍生物。
• 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。
• Nickel-catalyzed Kumada Cross-coupling Reaction for the Synthesis of 2,4-Diarylquinazolines
  作者：Xinglin Ye、Zhihan Yuan、Yirong Zhou、Qin Yang、Yepeng Xie、Zhihong Deng、Yiyuan Peng

  DOI：10.1002/jhet.2513

  日期：2016.11

  A series of 2,4‐diarylquinazolines have been successfully synthesized via the Ni‐catalyzed cross‐coupling reaction of quinazoline‐4‐tosylates and aryl Grignard reagents, which provided alternative straightforward approaches for the introduction of aryl groups to quinazolines at C‐4 position.