8-(4-acetylphenylethynyl)guanosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-(4-acetylphenylethynyl)guanosine
• 英文别名: 8-[2-(4-acetylphenyl)ethynyl]-2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• 化学式: C₂₀H₁₉N₅O₆
• 分子量: 425.401
• InChiKey: JYJVTEYHTRCZNJ-BGIGGGFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-乙炔基苯乙酮 、 8-溴鸟苷 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以68%的产率得到8-(4-acetylphenylethynyl)guanosine
  参考文献：
  名称：

  Sonogashira alkynylation of unprotected 8-brominated adenosines and guanosines: fluorescence properties of compact conjugated acetylenes containing a purine ring

  摘要：

  A practical Sonogashira alkynylation protocol for the preparation of 8-alkynylated adenosines and guanosines has been developed. Protection of the sugar hydroxyl substituents is not required; protection hinders the purification of these products. A preliminary fluorescent study is reported, which shows that the presence of a substituent on the phenylene ring influences the fluorescent properties considerably, an outcome that could be utilized in biological applications. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.100

文献信息

• Sonogashira alkynylation of unprotected 8-brominated adenosines and guanosines: fluorescence properties of compact conjugated acetylenes containing a purine ring
  作者：Andrew G. Firth、Ian J.S. Fairlamb、Kate Darley、Christoph G. Baumann

  DOI：10.1016/j.tetlet.2006.03.100

  日期：2006.5

  A practical Sonogashira alkynylation protocol for the preparation of 8-alkynylated adenosines and guanosines has been developed. Protection of the sugar hydroxyl substituents is not required; protection hinders the purification of these products. A preliminary fluorescent study is reported, which shows that the presence of a substituent on the phenylene ring influences the fluorescent properties considerably, an outcome that could be utilized in biological applications. (c) 2006 Elsevier Ltd. All rights reserved.