2,6-[bis-2,5-dimethoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)anilino-N-carbonyl]pyridine | 1004783-00-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,6-[bis-2,5-dimethoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)anilino-N-carbonyl]pyridine
• CAS: 1004783-00-9
• 化学式: C₅₁H₅₉N₃O₂₄
• 分子量: 1098.04
• InChiKey: KVQBUXZYMHQKMO-NOXPLDSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  78.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  336.87
• 氢给体数：
  2.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  2,6-[bis-2,5-dimethoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)anilino-N-carbonyl]pyridine 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以80%的产率得到2,6-bis[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-benzoquinone-5-amino-N-carbonyl]pyridine
  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：

  2,6-氯甲酰吡啶 、 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,5-dimethoxyaniline 、 乙醇 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到2,6-[bis-2,5-dimethoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)anilino-N-carbonyl]pyridine
  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