5-(5-bromothiophen-2-yl)-6-azauridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(5-bromothiophen-2-yl)-6-azauridine
• 英文别名: 6-(5-bromothiophen-2-yl)-2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazine-3,5-dione
• 化学式: C₁₂H₁₂BrN₃O₆S
• 分子量: 406.214
• InChiKey: JWIYNBCQRNHSON-KJZZYSIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(5-bromothiophen-2-yl)-6-azauridine 、 4-羟基苯硼酸 在 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 18.0h， 以74%的产率得到5-(5-(4-hydroxyphenyl)thiophen-2-yl)-6-azauridine
  参考文献：
  名称：

  Visibly Emissive and Responsive Extended 6-Aza-Uridines

  摘要：

  A family of extended 5-modified-6-aza-uridines was obtained via Suzuki coupling reactions with a common brominated precursor. Extending the conjugated-6-aza-uridines with substituted aryl rings increases the push-pull interactions yielding enhanced bathochromic shifts and solvatochromism compared to the parent nucleosides. For example, the methoxy substituted derivative 1d displays lambda(max) abs around 375 nm, with visible emission maxima at 486 nm (Phi = 0.74) and 525 nm (Phi = 0.02) in dioxane and water, respectively.

  DOI：

  10.1021/ol502435d
• 作为产物：
  描述：

  5-(5-bromothiophene-2-yl)-6-aza-2’,3’,5’-tribenzoyluridine 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以77%的产率得到5-(5-bromothiophen-2-yl)-6-azauridine
  参考文献：
  名称：

  Visibly Emissive and Responsive Extended 6-Aza-Uridines

  摘要：

  A family of extended 5-modified-6-aza-uridines was obtained via Suzuki coupling reactions with a common brominated precursor. Extending the conjugated-6-aza-uridines with substituted aryl rings increases the push-pull interactions yielding enhanced bathochromic shifts and solvatochromism compared to the parent nucleosides. For example, the methoxy substituted derivative 1d displays lambda(max) abs around 375 nm, with visible emission maxima at 486 nm (Phi = 0.74) and 525 nm (Phi = 0.02) in dioxane and water, respectively.

  DOI：

  10.1021/ol502435d