2,6-bis[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrooquinone-5-amino-N-carbonyl]pyridine | 1004783-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-bis[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrooquinone-5-amino-N-carbonyl]pyridine
• CAS: 1004783-29-2
• 化学式: C₄₇H₅₁N₃O₂₄
• 分子量: 1041.93
• InChiKey: IVSIXZKEKSDGPF-AQWKLMCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  74.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  380.87
• 氢给体数：
  6.0
• 氢受体数：
  25.0

反应信息

• 作为产物：
  描述：

  2,6-bis[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-benzoquinone-5-amino-N-carbonyl]pyridine 在 sodium dithionite 、 水 作用下， 以 氯仿 为溶剂， 反应 1.75h， 以85%的产率得到2,6-bis[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrooquinone-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