[1-(5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-5-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl](4-fluorophenyl)methanone | 1452830-81-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1-(5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-5-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl](4-fluorophenyl)methanone
• 英文别名: [1-[[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl]-5-(2-nitrophenyl)triazol-4-yl]-(4-fluorophenyl)methanone
• CAS: 1452830-81-7
• 化学式: C₂₃H₂₁FN₄O₇
• 分子量: 484.441
• InChiKey: CGEGFNMISHLWRY-IDZYALCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [1-(5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-5-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl](4-fluorophenyl)methanone 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以91%的产率得到1-(5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-4-(4-fluorophenyl)-1H-[1,2,3]triazolo[4,5-c]quinoline
  参考文献：
  名称：

  A strategy to access fused triazoloquinoline and related nucleoside analogues

  摘要：

  Fused triazoloquinolines have been prepared starting from (E)-3-(2-nitrophenyl)-1-aryl-prop-2-en-1-ones and sugar or benzyl azides in a sequential [3+2] cycloaddition reaction, followed by one pot Pd-C assisted reduction, cyclization and aromatization. The triazolyl fused quinolines with N-1-glycosyl substituents as unnatural nucleosides have inherent potential to generate a library of compounds for bioevaluations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.088
• 作为产物：
  描述：

  5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 、 (E)-1-(4-fluorophenyl)-3-(2-nitrophenyl)prop-2-en-1-one 在 四丁基硫酸氢铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以71%的产率得到[1-(5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-5-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl](4-fluorophenyl)methanone
  参考文献：
  名称：

  A strategy to access fused triazoloquinoline and related nucleoside analogues

  摘要：

  Fused triazoloquinolines have been prepared starting from (E)-3-(2-nitrophenyl)-1-aryl-prop-2-en-1-ones and sugar or benzyl azides in a sequential [3+2] cycloaddition reaction, followed by one pot Pd-C assisted reduction, cyclization and aromatization. The triazolyl fused quinolines with N-1-glycosyl substituents as unnatural nucleosides have inherent potential to generate a library of compounds for bioevaluations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.088

文献信息

• A strategy to access fused triazoloquinoline and related nucleoside analogues
  作者：Kapil Upadhyaya、Arya Ajay、Rohit Mahar、Renu Pandey、Brijesh Kumar、Sanjeev K. Shukla、Rama Pati Tripathi

  DOI：10.1016/j.tet.2013.07.088

  日期：2013.10

  Fused triazoloquinolines have been prepared starting from (E)-3-(2-nitrophenyl)-1-aryl-prop-2-en-1-ones and sugar or benzyl azides in a sequential [3+2] cycloaddition reaction, followed by one pot Pd-C assisted reduction, cyclization and aromatization. The triazolyl fused quinolines with N-1-glycosyl substituents as unnatural nucleosides have inherent potential to generate a library of compounds for bioevaluations. (C) 2013 Elsevier Ltd. All rights reserved.