2-<4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethoxyphenyl>-6-hydroxy-4H-benzopyran-4-one | 134178-14-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-<4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethoxyphenyl>-6-hydroxy-4H-benzopyran-4-one
• 英文别名: 2-[4-[Tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxyphenyl]-6-hydroxychromen-4-one
• CAS: 134178-14-6
• 化学式: C₂₃H₂₈O₆Si
• 分子量: 428.557
• InChiKey: XYEPSXSEENDOBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丁香酸甲酯 在 硫酸 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 2-<4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethoxyphenyl>-6-hydroxy-4H-benzopyran-4-one
  参考文献：
  名称：

  A short and facile synthetic route to hydroxylated flavones. New syntheses of apigenin, tricin, and luteolin

  摘要：

  Reaction of the lithium polyanions generated from omicron-hydroxyacetophenones 3a-f with O-silyloxylated benzoates 2a-d gave 1-aryl-3-(2-hydroxyphenyl)-1,3-propanediones 4a-n, which on treatment with acetic acid containing 0.5% H2SO4 at 95-100-degrees-C afforded hydroxylated flavones 5-18 in high yields (76-92%).

  DOI：

  10.1021/jo00016a015

文献信息

• A short and facile synthetic route to hydroxylated flavones. New syntheses of apigenin, tricin, and luteolin
  作者：Dhanapalan Nagarathnam、Mark Cushman

  DOI：10.1021/jo00016a015

  日期：1991.8

  Reaction of the lithium polyanions generated from omicron-hydroxyacetophenones 3a-f with O-silyloxylated benzoates 2a-d gave 1-aryl-3-(2-hydroxyphenyl)-1,3-propanediones 4a-n, which on treatment with acetic acid containing 0.5% H2SO4 at 95-100-degrees-C afforded hydroxylated flavones 5-18 in high yields (76-92%).