2-Methyl-4-(2-phenylethynyl)quinazoline | 1427059-59-3

• 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-4-(2-phenylethynyl)quinazoline
• CAS: 1427059-59-3
• 化学式: C₁₇H₁₂N₂
• 分子量: 244.296
• InChiKey: YXBMCNQCKULBBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-methyl-1,2,3,4-tetrahydroquinazoline 在 正丁基锂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 23.0h， 生成 2-Methyl-4-(2-phenylethynyl)quinazoline
  参考文献：
  名称：

  4-炔基喹唑啉的无过渡金属合成

  摘要：

  摘要。已经开发出允许在无过渡金属条件下轻松获得 4-炔基喹唑啉的协议。喹唑啉与苯并呋喃的芳基化反应得到4-(苯并呋喃-2-基)喹唑啉的开环反应是获得4-炔基喹唑啉的第一种方法。在正丁基锂和碘的存在下或用炔基格氏试剂将喹唑啉与末端炔烃直接炔基化是另一种策略。通过直接炔化获得的 4-((三甲基甲硅烷基)乙炔基)喹唑啉的去甲硅烷基化是获得 4-炔基喹唑啉的第三种方法。还表明该协议适用于放大合成。

  DOI：

  10.1002/ejoc.202200131

文献信息

• Sonogashira cross-coupling reaction in 4-chloro-2-trichloromethylquinazoline series is possible despite a side dimerization reaction
  作者：Charline Kieffer、Pierre Verhaeghe、Nicolas Primas、Caroline Castera-Ducros、Armand Gellis、Roselyne Rosas、Sylvain Rault、Pascal Rathelot、Patrice Vanelle

  DOI：10.1016/j.tet.2013.01.094

  日期：2013.4

  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.