3-((1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(trifluoromethyl)quinazolin-4(3H)-one | 1213232-34-8

• 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: 3-((1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(trifluoromethyl)quinazolin-4(3H)-one
• 英文别名: 3-[[1-(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctyl)triazol-4-yl]methyl]-2-(trifluoromethyl)quinazolin-4-one
• CAS: 1213232-34-8
• 化学式: C₂₀H₁₁F₁₆N₅O
• 分子量: 641.315
• InChiKey: JJJIEERTIODMLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.4
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  8-azido-1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane 、 3-(prop-2-ynyl)-2-(trifluoromethyl)quinazolin-4(3H)-one 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 以81.15%的产率得到3-((1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(trifluoromethyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Click chemistry: Studies on the synthesis of novel fluorous tagged triazol-4-yl substituted quinazoline derivatives and their biological evaluation – Theoretical and experimental validation

  摘要：

  The formation of N- and O-propargylated quinazoline derivatives 2, 3 from quinazol-4-ones 1 was theoretically predicted by optimizations at B3LYP/6-31G* level, analysed kinetically and thermodynamically. Theoretical predictions are validated by experiment to observe the trends and found deviation. Thus, compound I was propargylated in basic media to obtain compound 2 and 3 in definite proportions. Each compound was further subjected to [3 + 2] cycloaddition using perfluoroalkyl azides through Click reaction under Sharpless conditions, and obtained a series of novel perfluoroalkyl-1H,1,2,3-triazol-4-yl substituted quinazolines 4, 5, and 6. All the compounds were screened for antimicrobial activity and identified potential compounds. (C) 2009 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2009.09.027

文献信息

• Click chemistry: Studies on the synthesis of novel fluorous tagged triazol-4-yl substituted quinazoline derivatives and their biological evaluation – Theoretical and experimental validation
  作者：P. Mani Chandrika、T. Yakaiah、G. Gayatri、K. Pranay Kumar、B. Narsaiah、U.S.N. Murthy、A. Raghu Ram Rao

  DOI：10.1016/j.ejmech.2009.09.027

  日期：2010.1

  The formation of N- and O-propargylated quinazoline derivatives 2, 3 from quinazol-4-ones 1 was theoretically predicted by optimizations at B3LYP/6-31G* level, analysed kinetically and thermodynamically. Theoretical predictions are validated by experiment to observe the trends and found deviation. Thus, compound I was propargylated in basic media to obtain compound 2 and 3 in definite proportions. Each compound was further subjected to [3 + 2] cycloaddition using perfluoroalkyl azides through Click reaction under Sharpless conditions, and obtained a series of novel perfluoroalkyl-1H,1,2,3-triazol-4-yl substituted quinazolines 4, 5, and 6. All the compounds were screened for antimicrobial activity and identified potential compounds. (C) 2009 Published by Elsevier Masson SAS.