2-methyl-N-p-tolylquinazolin-4-amine | 677748-47-9

• 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: 2-methyl-N-p-tolylquinazolin-4-amine
• 英文别名: 2-methyl-N-(4-methylphenyl)quinazolin-4-amine
• CAS: 677748-47-9
• 化学式: C₁₆H₁₅N₃
• 分子量: 249.315
• InChiKey: YDHIIEHMAARDQN-UHFFFAOYSA-N

物化性质

• 熔点：
  265-268 °C
• 沸点：
  348.7±24.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-4(3H)-喹唑酮 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 1.0h， 生成 2-methyl-N-p-tolylquinazolin-4-amine
  参考文献：
  名称：

  Synthesis of Substituted Quinazolines: Application to the Synthesis of Verubulin

  摘要：

  Through newly adapted methodology, 2-methyl-3H-quinazolin-4-one was activated using a number of methods followed by displacement to afford 4-aminoquinazolines. The most useful of these processes utilize the p-toluenesulfonate ester or I-2/PPh3 activation. Using this methodology, the anticancer vascular targeting clinical candidate verubulin (1) was synthesized in a highly efficient manner.

  DOI：

  10.1080/00397911.2010.529730

文献信息

• A new DMAP-catalyzed and microwave-assisted approach for introducing heteroarylamino substituents at position-4 of the quinazoline ring
  作者：Armand Gellis、Charline Kieffer、Nicolas Primas、Gilles Lanzada、Michel Giorgi、Pierre Verhaeghe、Patrice Vanelle

  DOI：10.1016/j.tet.2014.09.024

  日期：2014.11

  We report herein a new methodology for synthesizing quinazoline derivatives bearing a heteroarylamino moiety at position-4 of the quinazoline ring. As an alternative to the Buchwald-Hartwig cross-coupling reaction, which appears, until now, as the only efficient way to react 4-chloroquinazolines with numerous amino nitrogen-containing heterocycles displaying poor nucleophilicity, we developed a DMAP-catalyzed reaction involving microwave irradiation. Optimization of the reaction conditions led to the use of 30 mol % of DMAP in toluene, using a monomode microwave reactor and sealed vials. Moreover, the SNAr reaction intermediate salt was isolated and fully characterized. Finally, the procedure was extended to two different 2-substituted-quinazoline series and also to various anilines, demonstrating that this approach was a general efficient way to access to such 4-substituted quinazoline scaffolds of high pharmaceutical interest. (C) 2014 Elsevier Ltd. All rights reserved.
• HILMY, KNALID MONAMED HASSAN;MOGENSEN, JZHUSTORGEN;REDERSEN, ERIK V., ACTA CHEM. SCAND., 41,(1987) N 6, 467-468
  作者：HILMY, KNALID MONAMED HASSAN、MOGENSEN, JZHUSTORGEN、REDERSEN, ERIK V.

  DOI：——

  日期：——
• Synthesis of Substituted Quinazolines: Application to the Synthesis of Verubulin
  作者：Jeffrey W. Lockman、Yevgeniya Klimova、Mark B. Anderson、J. Adam Willardsen

  DOI：10.1080/00397911.2010.529730

  日期：2012.6.15

  Through newly adapted methodology, 2-methyl-3H-quinazolin-4-one was activated using a number of methods followed by displacement to afford 4-aminoquinazolines. The most useful of these processes utilize the p-toluenesulfonate ester or I-2/PPh3 activation. Using this methodology, the anticancer vascular targeting clinical candidate verubulin (1) was synthesized in a highly efficient manner.