9-((1-(anthracen-1-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-purin-6-amine | 1222177-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 9-((1-(anthracen-1-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-purin-6-amine
• CAS: 1222177-22-1
• 化学式: C₂₃H₁₈N₈
• 分子量: 406.45
• InChiKey: KYSZFVVVGPVHHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  100.33
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  1-(叠氮甲基)蒽 、 N-9-propargyladenine 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 9-((1-(anthracen-1-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-purin-6-amine
  参考文献：
  名称：

  在 ESI 串联质谱法中荧光人胸苷酸合酶抑制剂类似物的新重排

  摘要：

  Cu(I) 催化的炔-叠氮化物环加成反应用于合成一系列基于蒽的人胸苷酸合酶 (hTS) 抑制剂类似物。三唑并蒽衍生物通过 ESI-MS/MS 进行表征，并在 ESI-MS/MS 中观察到新的重排反应。提出的机制是质子化的三唑并蒽衍生物形成碳正离子，然后碳正离子亲电攻击蒽部分，导致形成重排离子。此外，碳正离子更倾向于通过亲电取代机制攻击 γ 位置而不是蒽部分的 α 或 β 位置。

  DOI：

  10.1016/j.jasms.2009.11.004

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.