7-hydroxy-3-(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-yl)-4H-chromen-4-one | 943965-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-hydroxy-3-(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-yl)-4H-chromen-4-one
• 英文别名: 7-hydroxy-3-(4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)chromen-4-one
• CAS: 943965-71-7
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: OITBZTBDGBBNGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-hydroxy-3-(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-yl)-4H-chromen-4-one 在 18-冠醚-6 、 zinc diacetate 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 12.0h， 生成 7-(β-D-glucopyranosyloxy)-3-(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-yl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis ofO‐β‐D‐Glucopyranosides of 7‐Hydroxy‐3‐(imidazol‐2‐yl)‐4H‐chromen‐4‐ones

  摘要：

  The 7-hydroxy-3-formyl-4H-chromen-4-one 1 reacted with various cyclic 1,2-dicarbonyl compounds in the presence of ammonium acetate to furnish 7-hydroxy-3-([4,5-fused] imidazol-2-yl)-4H-chromen-4-ones 2a-f, which on glucosylation with alpha-acetobromoglucose affords 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy-3-([4,5-fused]-imidazol-2-yl)-4H-chromen-4-ones3a-f. 7-O-beta-D-Glucopyranosyloxy-3-([4,5-fused]-imidazol-2-yl)-4H- chromen-4-ones4a-f were prepared by deacetylation with anhydrous zinc acetate in absolute methanol. The structure of these new O-beta-D-glucosides was established on the basis of chemical, elemental, and spectral analysis. These compounds were evaluated for their in vitro biological activity.[GRAPHICS]

  DOI：

  10.1080/07328300701298196
• 作为产物：
  描述：

  7-羟基-4-氧代-4H-1-苯并吡喃-3-羧醛 、 1,2-环己二酮 在 乙酸铵 、 溶剂黄146 作用下， 反应 2.0h， 以67%的产率得到7-hydroxy-3-(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-yl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis ofO‐β‐D‐Glucopyranosides of 7‐Hydroxy‐3‐(imidazol‐2‐yl)‐4H‐chromen‐4‐ones

  摘要：

  The 7-hydroxy-3-formyl-4H-chromen-4-one 1 reacted with various cyclic 1,2-dicarbonyl compounds in the presence of ammonium acetate to furnish 7-hydroxy-3-([4,5-fused] imidazol-2-yl)-4H-chromen-4-ones 2a-f, which on glucosylation with alpha-acetobromoglucose affords 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy-3-([4,5-fused]-imidazol-2-yl)-4H-chromen-4-ones3a-f. 7-O-beta-D-Glucopyranosyloxy-3-([4,5-fused]-imidazol-2-yl)-4H- chromen-4-ones4a-f were prepared by deacetylation with anhydrous zinc acetate in absolute methanol. The structure of these new O-beta-D-glucosides was established on the basis of chemical, elemental, and spectral analysis. These compounds were evaluated for their in vitro biological activity.[GRAPHICS]

  DOI：

  10.1080/07328300701298196