ethyl 2-(methylthio)-4-(phenylethynyl)pyrimidine-5-carboxylate | 1005161-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 2-(methylthio)-4-(phenylethynyl)pyrimidine-5-carboxylate
• 英文别名: ethyl 2-methylsulfanyl-4-(2-phenylethynyl)pyrimidine-5-carboxylate
• CAS: 1005161-88-5
• 化学式: C₁₆H₁₄N₂O₂S
• 分子量: 298.365
• InChiKey: DZLBEQUXMIAXDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(methylthio)-4-(phenylethynyl)pyrimidine-5-carboxylate 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 反应 0.33h， 以91%的产率得到2-(methylthio)-7-phenyl-5H-pyrano[4,3-b]pyrimidin-5-one
  参考文献：
  名称：

  6-endo-dig Cyclization of heteroarylesters to alkynes promoted by Lewis acid catalyst in the presence of Brønsted acid

  摘要：

  We report a regiocontrolled 6-endo-dig cyclization of 2-(2-arylethynyl)heteroaryl esters occurred under Bronsted acidic conditions and in the presence of a catalytic amount of Lewis acids such as Cu(OTf)(2), AUCl(3), or (CF3CO2)Ag. A variety of heteroc yclic lactones are readily prepared in excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.020
• 作为产物：
  描述：

  苯乙炔 、 ethyl 4-iodo-2-(methylthio)pyrimidine-5-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以73%的产率得到ethyl 2-(methylthio)-4-(phenylethynyl)pyrimidine-5-carboxylate
  参考文献：
  名称：

  6-endo-dig Cyclization of heteroarylesters to alkynes promoted by Lewis acid catalyst in the presence of Brønsted acid

  摘要：

  We report a regiocontrolled 6-endo-dig cyclization of 2-(2-arylethynyl)heteroaryl esters occurred under Bronsted acidic conditions and in the presence of a catalytic amount of Lewis acids such as Cu(OTf)(2), AUCl(3), or (CF3CO2)Ag. A variety of heteroc yclic lactones are readily prepared in excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.020