3-(4-phenyl-4H-1,2,4-triazol-3-yl)-7-O-(β-D-tetraacetylglucopyranosyl)-2H-chromen-2-one | 1210915-34-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(4-phenyl-4H-1,2,4-triazol-3-yl)-7-O-(β-D-tetraacetylglucopyranosyl)-2H-chromen-2-one
• CAS: 1210915-34-6
• 化学式: C₃₁H₂₉N₃O₁₂
• 分子量: 635.584
• InChiKey: WSBARUAEXHDVRD-DWKUPSHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  46.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  184.58
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  3-(4-phenyl-4H-1,2,4-triazol-3-yl)-7-O-(β-D-tetraacetylglucopyranosyl)-2H-chromen-2-one 在 甲醇 、 sodium methylate 作用下， 反应 24.0h， 以100%的产率得到7-O-(β-D-glucopyranosyl)-3-(4-phenyl-4H-1,2,4-triazol-3-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Highly efficient glucosylation of flavonoids

  摘要：

  A highly efficient procedure for glucosylation of flavonoids by acetobromoglucose is described. Glucosylation is carried out in a two-phase system CHCl3/H2O over 96 h using tetrabutylammonium bromide as phase-transfer catalyst. A purification procedure can be performed without column chromatography, and the yields of the glucosylated flavonoids are mostly quantitative. Acetylated glucosides were deprotected with sodium methanolate to afford the desired glucosides of flavonoids.

  DOI：

  10.1007/s00706-009-0207-6
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 、 7-hydroxy-3-(4-phenyl-4H-1,2,4-triazol-3-yl)-2H-chromen-2-one 在 potassium carbonate 、 四丁基溴化铵 作用下， 以 水 、 氯仿 为溶剂， 反应 96.0h， 以100%的产率得到3-(4-phenyl-4H-1,2,4-triazol-3-yl)-7-O-(β-D-tetraacetylglucopyranosyl)-2H-chromen-2-one
  参考文献：
  名称：

  Highly efficient glucosylation of flavonoids

  摘要：

  A highly efficient procedure for glucosylation of flavonoids by acetobromoglucose is described. Glucosylation is carried out in a two-phase system CHCl3/H2O over 96 h using tetrabutylammonium bromide as phase-transfer catalyst. A purification procedure can be performed without column chromatography, and the yields of the glucosylated flavonoids are mostly quantitative. Acetylated glucosides were deprotected with sodium methanolate to afford the desired glucosides of flavonoids.

  DOI：

  10.1007/s00706-009-0207-6