ethyl α-fluoro-α-[(3,4-dihydro-4-oxo-3-phenyl-2-quinazolinyl)thio]acetate | 250690-57-4

• 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: ethyl α-fluoro-α-[(3,4-dihydro-4-oxo-3-phenyl-2-quinazolinyl)thio]acetate
• 英文别名: Ethyl 2-fluoro-2-(4-oxo-3-phenylquinazolin-2-yl)sulfanylacetate
• CAS: 250690-57-4
• 化学式: C₁₈H₁₅FN₂O₃S
• 分子量: 358.393
• InChiKey: VFXSEXIZBRHXDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl α-fluoro-α-[(3,4-dihydro-4-oxo-3-phenyl-2-quinazolinyl)thio]acetate 在 四乙基氟化铵水合物 作用下， 以 乙二醇二甲醚 为溶剂， 以14%的产率得到3,4-dihydro-2-fluoro-4-oxo-3-phenylquinazoline
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 35.¹ Anodic Fluorination of 2-Pyrimidyl, 2-Pyridyl, and 2-Quinazolinonyl Sulfides

  摘要：

  Highly regioselective electrochemical fluorination of 2-pyrimidyl sulfides having an electron(EWG) withdrawing group at the position alpha to the sulfur atom was successfully carried out using Et4NF . nHF (n = 3, 4) or Et3N . 3HF as a supporting electrolyte and a fluoride ion source in 1,2-dimethoxyethane (DME) in an undivided cell. 2-Methylthiopyrimidine devoid of an EWG was also selectively fluorinated in DME to provide 2-(fluoromethylthio)pyrimidine in a moderate yield as 63%, while corresponding 2-methylthiopyridine was less selectively fluorinated in lower yield along with alpha,alpha-difluorinated product. In contrast, the corresponding 2-quinazolinonyl sulfides underwent similarly alpha-fluorination along with unexpected ipso-fluorination through anodic desulfurization.

  DOI：

  10.1021/jo9909857
• 作为产物：
  描述：

  3-苯基-2-硫代-2,3-二氢-4(1H)-喹唑啉酮 在 四乙基氟化铵水合物 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 3.5h， 生成 ethyl α-fluoro-α-[(3,4-dihydro-4-oxo-3-phenyl-2-quinazolinyl)thio]acetate
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 35.¹ Anodic Fluorination of 2-Pyrimidyl, 2-Pyridyl, and 2-Quinazolinonyl Sulfides

  摘要：

  Highly regioselective electrochemical fluorination of 2-pyrimidyl sulfides having an electron(EWG) withdrawing group at the position alpha to the sulfur atom was successfully carried out using Et4NF . nHF (n = 3, 4) or Et3N . 3HF as a supporting electrolyte and a fluoride ion source in 1,2-dimethoxyethane (DME) in an undivided cell. 2-Methylthiopyrimidine devoid of an EWG was also selectively fluorinated in DME to provide 2-(fluoromethylthio)pyrimidine in a moderate yield as 63%, while corresponding 2-methylthiopyridine was less selectively fluorinated in lower yield along with alpha,alpha-difluorinated product. In contrast, the corresponding 2-quinazolinonyl sulfides underwent similarly alpha-fluorination along with unexpected ipso-fluorination through anodic desulfurization.

  DOI：

  10.1021/jo9909857