3-(4-((((2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(((1-(7-hydroxy-2-oxo-2H-chromen-3-yl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)-7-hydroxy-2H-chromen-2-one | 1415679-86-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(4-((((2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(((1-(7-hydroxy-2-oxo-2H-chromen-3-yl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)-7-hydroxy-2H-chromen-2-one
• CAS: 1415679-86-5
• 化学式: C₃₁H₂₈N₆O₁₂
• 分子量: 676.596
• InChiKey: OINGXRJIYPIZSL-QWCZOQLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  49.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  239.68
• 氢给体数：
  4.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  7-hydroxy-3-[4-[[(2R,3R,4S,5R,6S)-3-[[1-(7-hydroxy-2-oxochromen-3-yl)triazol-4-yl]methoxy]-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methoxymethyl]triazol-1-yl]chromen-2-one 在 氢气 、 palladium dichloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以96.3%的产率得到3-(4-((((2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(((1-(7-hydroxy-2-oxo-2H-chromen-3-yl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)-7-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction

  摘要：

  Glycoligands, which feature a glycoside as the central template incorporating Lewis bases as metal chelation sites and various fluorophores as the chemical reporter, represent a range of interesting scaffolds for development of chemosensors. Here, new types of triazolyl bidentate glycoligands (TBGs) based on the grafting of 3-azidocoumarin to the C2,3- or C4,6-positions of three epimeric pyranoglycosides including a glucoside, a galactoside, and a mannoside were efficiently synthesized via a fluorogenic dual click reaction assisted by microwave irradiation. The desired TBGs were afforded in high conversion rates (>90%) and reasonable yields (similar to 70%). Moreover, a preliminary optical study of two hydroxyl-free glucoside-based TBGs indicates that these compounds are strongly fluorescent in pure water, implying their potential for ion detections in aqueous media. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.10.001