1-(2,5-dihydroxy-4,6-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2,5-dihydroxy-4,6-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone
• 英文别名: (E)-1-(3,6-dihydroxy-2,4-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₉H₂₀O₇
• 分子量: 360.364
• InChiKey: BXPLEEFLXIETOG-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2,5-dihydroxy-4,6-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone 在 吡啶 、 碘 、 二甲基二环氧乙烷 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 20.83h， 生成 川陈皮素
  参考文献：
  名称：

  Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

  摘要：

  The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3',4',5,6,7,8-heptamethoxyflavone, quercetin and its derivatives were synthesized. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.023
• 作为产物：
  描述：

  2',4',6',3,4-Pentamethoxychalkone 在 二甲基二环氧乙烷 、 三溴化硼 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.5h， 生成 1-(2,5-dihydroxy-4,6-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone
  参考文献：
  名称：

  Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

  摘要：

  The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3',4',5,6,7,8-heptamethoxyflavone, quercetin and its derivatives were synthesized. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.023

文献信息

• Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids
  作者：Han-Wei Chu、Huan-Ting Wu、Yean-Jang Lee

  DOI：10.1016/j.tet.2004.01.023

  日期：2004.3

  The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3',4',5,6,7,8-heptamethoxyflavone, quercetin and its derivatives were synthesized. (C) 2004 Elsevier Ltd. All rights reserved.