4-(2-nitrobenzyl)-2-trifluoromethylquinazoline | 1314885-45-4

• 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: 4-(2-nitrobenzyl)-2-trifluoromethylquinazoline
• 英文别名: 4-[(2-Nitrophenyl)methyl]-2-(trifluoromethyl)quinazoline；4-[(2-nitrophenyl)methyl]-2-(trifluoromethyl)quinazoline
• CAS: 1314885-45-4
• 化学式: C₁₆H₁₀F₃N₃O₂
• 分子量: 333.27
• InChiKey: AFKOATSFSKWLPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 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：
  71.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-硝基苄氯 、 4-氯-2-三氟甲基喹唑啉 在 四(二甲氨基)乙烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 以90%的产率得到4-(2-nitrobenzyl)-2-trifluoromethylquinazoline
  参考文献：
  名称：

  First SNAr reaction using TDAE-initiated carbanions in quinazoline series

  摘要：

  We report herein the first example of a SNAr reaction using TDAE-initiated carbanions in quinazoline series. The o-nitrobenzyl carbanion, formed by the action of TDAE on o-nitrobenzyl chloride, reacts with 4-chloro-2-trihalomethylquinazolines 4 and 5 via a SNAr mechanism. This enabled a new series of 4-benzyl-2-trihaloquinazoline derivatives to be synthesized in good yields under mild reaction conditions offering promising prospects for pharmacomodulation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.060

文献信息

• First SNAr reaction using TDAE-initiated carbanions in quinazoline series
  作者：Marc Since、Omar Khoumeri、Pierre Verhaeghe、Martine Maillard-Boyer、Thierry Terme、Patrice Vanelle

  DOI：10.1016/j.tetlet.2011.05.060

  日期：2011.7

  We report herein the first example of a SNAr reaction using TDAE-initiated carbanions in quinazoline series. The o-nitrobenzyl carbanion, formed by the action of TDAE on o-nitrobenzyl chloride, reacts with 4-chloro-2-trihalomethylquinazolines 4 and 5 via a SNAr mechanism. This enabled a new series of 4-benzyl-2-trihaloquinazoline derivatives to be synthesized in good yields under mild reaction conditions offering promising prospects for pharmacomodulation. (C) 2011 Elsevier Ltd. All rights reserved.