4,6-dimethoxy-1aphenyl-1aH-oxireno[2,3-b]chromen-7(7aH)-one | 1265223-29-7

• 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: 4,6-dimethoxy-1aphenyl-1aH-oxireno[2,3-b]chromen-7(7aH)-one
• 英文别名: 4,6-dimethoxy-1a-phenyl-7aH-oxireno[2,3-b]chromen-7-one
• CAS: 1265223-29-7
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: TZZYUZZYDGLOOW-UHFFFAOYSA-N

物化性质

• 沸点：
  498.1±45.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,6-dimethoxy-1aphenyl-1aH-oxireno[2,3-b]chromen-7(7aH)-one 在 盐酸 、 水 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以60%的产率得到2-hydroxy-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione
  参考文献：
  名称：

  Use of acyl substituents to favour 2,3-epoxidation of 5,7-dioxygenated flavones with dimethyldioxirane

  摘要：

  The reaction of 5,7-dimethoxyflavone with dimethyldioxirane (DMDO) gives the 2,3-epoxide rapidly at first. However, low levels of ring A hydroxylated by-products are also formed. With increasing proportions of DMDO, demethylation at C-5 becomes apparent and consumption of substrate is not matched by further significant build-up of the epoxide. Deactivation of ring A by the use of acyl groups removes this complication. 5,7-Diacylflavones give excellent yields of epoxides and monoacyl derivatives also react in good yield. Ionization potential mans derived from density functional theory calculations (B3LYP/6-31G*), provide good visual indicators of the relative reactivity of the key nucleophilic loci. The epoxides may be isolated as such, or transformed into flavonols by treatment with p-toluenesulfonic acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.076
• 作为产物：
  描述：

  柯因二甲醚 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以10%的产率得到4,6-dimethoxy-1aphenyl-1aH-oxireno[2,3-b]chromen-7(7aH)-one
  参考文献：
  名称：

  Use of acyl substituents to favour 2,3-epoxidation of 5,7-dioxygenated flavones with dimethyldioxirane

  摘要：

  The reaction of 5,7-dimethoxyflavone with dimethyldioxirane (DMDO) gives the 2,3-epoxide rapidly at first. However, low levels of ring A hydroxylated by-products are also formed. With increasing proportions of DMDO, demethylation at C-5 becomes apparent and consumption of substrate is not matched by further significant build-up of the epoxide. Deactivation of ring A by the use of acyl groups removes this complication. 5,7-Diacylflavones give excellent yields of epoxides and monoacyl derivatives also react in good yield. Ionization potential mans derived from density functional theory calculations (B3LYP/6-31G*), provide good visual indicators of the relative reactivity of the key nucleophilic loci. The epoxides may be isolated as such, or transformed into flavonols by treatment with p-toluenesulfonic acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.076

文献信息

• Use of acyl substituents to favour 2,3-epoxidation of 5,7-dioxygenated flavones with dimethyldioxirane
  作者：Benjamin J. Compton、Lesley Larsen、Rex T. Weavers

  DOI：10.1016/j.tet.2010.11.076

  日期：2011.1

  The reaction of 5,7-dimethoxyflavone with dimethyldioxirane (DMDO) gives the 2,3-epoxide rapidly at first. However, low levels of ring A hydroxylated by-products are also formed. With increasing proportions of DMDO, demethylation at C-5 becomes apparent and consumption of substrate is not matched by further significant build-up of the epoxide. Deactivation of ring A by the use of acyl groups removes this complication. 5,7-Diacylflavones give excellent yields of epoxides and monoacyl derivatives also react in good yield. Ionization potential mans derived from density functional theory calculations (B3LYP/6-31G*), provide good visual indicators of the relative reactivity of the key nucleophilic loci. The epoxides may be isolated as such, or transformed into flavonols by treatment with p-toluenesulfonic acid. (C) 2010 Elsevier Ltd. All rights reserved.