{10-[4-(4-三氟甲基-苯基)-[1,2,3]三唑-1-基甲基]-蒽-9-基}-甲醇 | 1019335-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: {10-[4-(4-三氟甲基-苯基)-[1,2,3]三唑-1-基甲基]-蒽-9-基}-甲醇
• 英文名称: {10-[4-(4-trifluoromethyl-phenyl)-[1,2,3]triazol-1-ylmethyl]-anthracen-9-yl}-methanol
• 英文别名: [10-[[4-[4-(Trifluoromethyl)phenyl]triazol-1-yl]methyl]anthracen-9-yl]methanol
• CAS: 1019335-88-6
• 化学式: C₂₅H₁₈F₃N₃O
• 分子量: 433.433
• InChiKey: IDKLMTXLTWFTQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (10-azidomethylanthracen-9-yl)methanol 、 4-乙炔基-α,α,α-三氟甲苯 在 copper(I) sulfate 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 为溶剂， 以79%的产率得到{10-[4-(4-三氟甲基-苯基)-[1,2,3]三唑-1-基甲基]-蒽-9-基}-甲醇
  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

文献信息

• A fluorogenic ‘click’ reaction of azidoanthracene derivatives
  作者：Fang Xie、Krishnamoorthy Sivakumar、Qingbing Zeng、Michael A. Bruckman、Blake Hodges、Qian Wang

  DOI：10.1016/j.tet.2008.01.080

  日期：2008.3

  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.