4-cyclohexyl-2-phenyl-7-trifluoromethylquinazoline

• 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-cyclohexyl-2-phenyl-7-trifluoromethylquinazoline
• 英文别名: 4-cyclohexyl-2-phenyl-4-trifluoromethylquinazoline；2-Phenyl-4-cyclohexyl-7-(trifluoromethyl)quinazoline；4-cyclohexyl-2-phenyl-7-(trifluoromethyl)quinazoline
• 化学式: C₂₁H₁₉F₃N₂
• 分子量: 356.39
• InChiKey: ITYMJDNPSXFRRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(3-三氟甲基-苯基)-苯甲酰胺 、 环己甲腈 在 2-氯吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以61%的产率得到4-cyclohexyl-2-phenyl-7-trifluoromethylquinazoline
  参考文献：
  名称：

  合成嘧啶衍生物的新策略。

  摘要：

  描述了嘧啶合成的最新进展。涉及NCN片段与1，3-二羰基衍生物缩合的常规策略的修改仍然是当前文献中的共同主题。其他方法，包括NC片段缩合策略，提供了能够分子内环化和形成嘧啶衍生物的反应性中间体。这些最近开发的方法为氮杂杂环合成提供了宝贵的补充。

  DOI：

  10.1002/chem.200800014

文献信息

• Direct Synthesis of Substituted Pyrimidines and Quinazolines
  作者：Mohammad Movassaghi、Matthew Hill

  DOI：10.1055/s-2007-990932

  日期：2008.3

  A variety of N-vinyl and N-aryl amides were converted in one step into the corresponding pyrimidine and quinazoline derivatives, respectively. Amide activation with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine followed by nitrile addition to the activated amide derivative and annulation provides the desired azaheterocycles.

  各种 N-乙烯基和 N-芳基酰胺在一个步骤中分别转化为相应的嘧啶和喹唑啉衍生物。在 2-氯吡啶存在下，先用三氟甲磺酸酐进行酰胺活化，然后将腈加到活化的酰胺衍生物中并环化，就得到了所需的杂杂环。
• Observations on the use of microwave irradiation in azaheterocycle synthesis
  作者：Matthew D. Hill、Mohammad Movassaghi

  DOI：10.1016/j.tetlet.2008.04.143

  日期：2008.6

  A comparison of conventional heating and microwave irradiation in the synthesis of azaheterocycles is discussed. Microwave irradiation was found to increase the yields of the desired products, shorten the reaction times, and extended this chemistry to recalcitrant amide substrates and weak nucleophiles. (C) 2008 Elsevier Ltd. All rights reserved.
• Single-Step Synthesis of Pyrimidine Derivatives
  作者：Mohammad Movassaghi、Matthew D. Hill

  DOI：10.1021/ja066405m

  日期：2006.11.1

  We describe a single-step conversion of various N-vinyl and N-aryl amides to the corresponding pyrimidine and quinazoline derivatives, respectively. The process involves amide activation with 2-chloropyridine and trifluoromethanesulfonic anhydride followed by nitrile addition into the reactive intermediate and cycloisomerization. In situ nitrile generation from primary amides allows for their use as nitrile surrogates. The use of this chemistry with sensitive N-vinyl amides and epimerizable substrates in addition to a wide range of functional groups is noteworthy.