4-[(2-Methoxyphenyl)ethynyl]-2-trichloromethyl-quinazoline | 1427059-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-[(2-Methoxyphenyl)ethynyl]-2-trichloromethyl-quinazoline
• 英文别名: 4-[2-(2-Methoxyphenyl)ethynyl]-2-(trichloromethyl)quinazoline
• CAS: 1427059-81-1
• 化学式: C₁₈H₁₁Cl₃N₂O
• 分子量: 377.657
• InChiKey: MNJLXJQPVLUZPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙炔基苯甲醚 、 4-氯-2-三氯甲基喹唑啉 在 copper(l) iodide 、 palladium diacetate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以18%的产率得到4-[(2-Methoxyphenyl)ethynyl]-2-trichloromethyl-quinazoline
  参考文献：
  名称：

  Sonogashira cross-coupling reaction in 4-chloro-2-trichloromethylquinazoline series is possible despite a side dimerization reaction

  摘要：

  We studied the Sonogashira coupling reaction between 4-chloro-2-trichloromethylquinazoline and various terminal alkynes, mainly in phenylacetylene series. A brief review of the literature shows that mono- or polybromo/chloromethylated substrates, especially in aromatic series, are very rarely compatible with the achievement of Sonogashira reactions. Thus, although the 4-chloroquinazoline scaffold is a very good substrate for this palladium-catalyzed reaction, the typical behavior of the trichloromethyl group in reductive media leads to the competitive formation of undesirable reduced homodimers in high yields. However, by closely examining all the Sonogashira reaction parameters, we developed a specific operating procedure, using Pd(OAc)(2), Cs2CO3, and DMF, which resulted in the synthesis of 14 original coupling products in 10-70% yield, depending on the alkyne used. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.094