[1-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-5-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl](m-tolyl)methanone | 1452830-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [1-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-5-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl](m-tolyl)methanone
• CAS: 1452830-84-0
• 化学式: C₂₈H₃₀N₄O₈
• 分子量: 550.568
• InChiKey: XWLFSENJFLRWCF-WTBZFEMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  40.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  137.07
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  [1-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-5-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl](m-tolyl)methanone 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 13.0h， 以81%的产率得到1-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-4-(m-tolyl)-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：

  6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-D-galactopyranose 、 (E)-1-(m-tolyl)-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72%的产率得到[1-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-5-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl](m-tolyl)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