(1-anthracen-9-ylmethyl-1H-[1,2,3]triazol-4-yl)-(4-nitrophenyl)-methanone | 1262850-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (1-anthracen-9-ylmethyl-1H-[1,2,3]triazol-4-yl)-(4-nitrophenyl)-methanone
• 英文别名: (4-Nitrophenyl) 1-(anthracen-9-ylmethyl)triazole-4-carboxylate；(4-nitrophenyl) 1-(anthracen-9-ylmethyl)triazole-4-carboxylate
• CAS: 1262850-11-2
• 化学式: C₂₄H₁₆N₄O₄
• 分子量: 424.415
• InChiKey: KKJNZIWBNAIFLR-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：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1-anthracen-9-ylmethyl-1H-[1,2,3]triazol-4-yl)-(4-nitrophenyl)-methanone 、 单-6-O-氨基-Β-环糊精 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以80%的产率得到mono-[6-(9-anthryl-1H-[1,2,3]triazole formamido)-6-deoxy]-β-cyclodextrin
  参考文献：
  名称：

  Synthesis and inclusion ability of anthracene appended β-cyclodextrins: unexpected effect of triazole linker

  摘要：

  A new fluorescent beta-cyclodextrin has been synthesized by coupling an anthracene moiety to the cyclic oligosaccharide via click chemistry. The influence of the triazole spacer was compared to the simple amino and amido linkers. While a sensing ability toward adamantan-1-ol was observed with the latter two spacers, the absence of inclusion capacity prevents the triazole modified cyclodextrin from showing any fluorescence variations. The difference in the binding behaviors studied by Isothermal Titration Calorimetry, UV-vis and fluorescence spectroscopies, was highlighted by the NOESY NMR spectra of the modified cyclodextrins: whereas a free cavity was observed for the amino and amido linkers, an important obstruction was obtained in the case of the triazole. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.09.031
• 作为产物：
  描述：

  4-nitrophenyl propiolate 、 9-(azidomethyl)anthracene 在 copper(l) iodide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 168.0h， 以72%的产率得到(1-anthracen-9-ylmethyl-1H-[1,2,3]triazol-4-yl)-(4-nitrophenyl)-methanone
  参考文献：
  名称：

  Synthesis and inclusion ability of anthracene appended β-cyclodextrins: unexpected effect of triazole linker

  摘要：

  A new fluorescent beta-cyclodextrin has been synthesized by coupling an anthracene moiety to the cyclic oligosaccharide via click chemistry. The influence of the triazole spacer was compared to the simple amino and amido linkers. While a sensing ability toward adamantan-1-ol was observed with the latter two spacers, the absence of inclusion capacity prevents the triazole modified cyclodextrin from showing any fluorescence variations. The difference in the binding behaviors studied by Isothermal Titration Calorimetry, UV-vis and fluorescence spectroscopies, was highlighted by the NOESY NMR spectra of the modified cyclodextrins: whereas a free cavity was observed for the amino and amido linkers, an important obstruction was obtained in the case of the triazole. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.09.031

文献信息

• Synthesis and inclusion ability of anthracene appended β-cyclodextrins: unexpected effect of triazole linker
  作者：Isabelle Mallard、David Landy、Nadia Bouchemal、Sophie Fourmentin

  DOI：10.1016/j.carres.2010.09.031

  日期：2011.1

  A new fluorescent beta-cyclodextrin has been synthesized by coupling an anthracene moiety to the cyclic oligosaccharide via click chemistry. The influence of the triazole spacer was compared to the simple amino and amido linkers. While a sensing ability toward adamantan-1-ol was observed with the latter two spacers, the absence of inclusion capacity prevents the triazole modified cyclodextrin from showing any fluorescence variations. The difference in the binding behaviors studied by Isothermal Titration Calorimetry, UV-vis and fluorescence spectroscopies, was highlighted by the NOESY NMR spectra of the modified cyclodextrins: whereas a free cavity was observed for the amino and amido linkers, an important obstruction was obtained in the case of the triazole. (C) 2010 Elsevier Ltd. All rights reserved.