2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxy-5-(4-aminobenzamido)benzene | 1004783-30-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxy-5-(4-aminobenzamido)benzene
• CAS: 1004783-30-5
• 化学式: C₂₉H₃₄N₂O₁₂
• 分子量: 602.595
• InChiKey: BFTHKNBYIJYGNG-VFHRMQJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  188.01
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  烟酰氯 、 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxy-5-(4-aminobenzamido)benzene 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以71%的产率得到2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxy-5-(4-nicotinamidobenzamido)benzene
  参考文献：
  名称：

  C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation

  摘要：

  Reaction of C-beta-D-glycopyranosyl-1,4-dimethoxybenzenes with acetyl nitrate afforded 2-(beta-D-glycopyranosyl)-1,4-dimethoxy-5-nitrobenzenes in high yields. These were converted smoothly (reduction to amines, N-acylation, oxidation, and reduction) into the corresponding C-glycosyl-hydro(benzo)quinone derivatives, with different amide-based substituents at C-5. Reduction of the nitro compounds to amines proceeded smoothly by catalytic hydrogen transfer with HCO2NH4.

  DOI：

  10.1055/s-2007-990856
• 作为产物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxy-5-(4-nitrobenzamido)benzene 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 1.25h， 以86%的产率得到2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxy-5-(4-aminobenzamido)benzene
  参考文献：
  名称：

  C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation

  摘要：

  Reaction of C-beta-D-glycopyranosyl-1,4-dimethoxybenzenes with acetyl nitrate afforded 2-(beta-D-glycopyranosyl)-1,4-dimethoxy-5-nitrobenzenes in high yields. These were converted smoothly (reduction to amines, N-acylation, oxidation, and reduction) into the corresponding C-glycosyl-hydro(benzo)quinone derivatives, with different amide-based substituents at C-5. Reduction of the nitro compounds to amines proceeded smoothly by catalytic hydrogen transfer with HCO2NH4.

  DOI：

  10.1055/s-2007-990856