10-((4-(prop-1-en-2-yl)-1H-1,2,3-triazol-1-yl)methyl)anthracene-9-carbonitrile | 1019337-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 10-((4-(prop-1-en-2-yl)-1H-1,2,3-triazol-1-yl)methyl)anthracene-9-carbonitrile
• CAS: 1019337-11-1
• 化学式: C₂₁H₁₆N₄
• 分子量: 324.385
• InChiKey: WIZSQQLRXIPXNP-UHFFFAOYSA-N

物化性质

• 沸点：
  598.4±52.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.5
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  10-azidomethylanthracene-9-carbonitrile 、 2-甲基-1-丁烯-3-炔 在 copper(I) sulfate 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 10-((4-(prop-1-en-2-yl)-1H-1,2,3-triazol-1-yl)methyl)anthracene-9-carbonitrile
  参考文献：
  名称：

  A fluorogenic ‘click’ reaction of azidoanthracene derivatives

  摘要：

  Fluorogenic reactions have broad applications in biolabeling, combinatorial synthesis of fluorescent dyes, and materials development. It was recently reported that the highly selective and efficient Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction can be employed in designing new types of fluorogenic reactions. In this study, we report a fluorogenic reaction using anthracene azides as starting materials. The fluorescence of the anthryl core can be greatly inhibited upon introducing electron-donating azido groups in the proximity. Such weakly fluorescent anthracene azides demonstrate high reactivity with a variety of alkynes under the CuAAC conditions producing a strongly fluorescent triazole product with high quantum yields. This reaction can be used in the synthesis and screening of fluorescent dyes combinatorially. Compared with most existing methods, the fluorogenic CuAAC reaction is a much milder and simpler technique to prepare large libraries of fluorescent dyes without further purification. In order to demonstrate the efficiency of using anthracene azides for biolabeling applications, both small molecules and biomolecules including the multialkyne-derivatized cowpea mosaic virus and tobacco mosaic virus had been studied. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.080