2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxy-5-(3,5-dimethoxybenzamido)benzene | 1004782-91-5

• 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-(3,5-dimethoxybenzamido)benzene
• CAS: 1004782-91-5
• 化学式: C₃₁H₃₇NO₁₄
• 分子量: 647.633
• InChiKey: XLFGPCWFODLJKE-MYOTWTRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  180.45
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxy-5-(3,5-dimethoxybenzamido)benzene 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以97%的产率得到2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(3,5-dimethoxybenzamido)-1,4-benzoquinone
  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：

  4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,5-dimethoxyaniline 、 3,5-二甲氧基苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxy-5-(3,5-dimethoxybenzamido)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