1-(2-hydroxy-4,6-bismethoxymethoxyphenyl)-3-(3-methoxy-4,5-bis-methoxymethoxyphenyl)propenoate | 297132-90-2

• 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-hydroxy-4,6-bismethoxymethoxyphenyl)-3-(3-methoxy-4,5-bis-methoxymethoxyphenyl)propenoate
• 英文别名: (E)-1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-[3-methoxy-4,5-bis(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 297132-90-2
• 化学式: C₂₄H₃₀O₁₁
• 分子量: 494.496
• InChiKey: NNQAQRVRADUYMW-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-4,6-bismethoxymethoxyphenyl)-3-(3-methoxy-4,5-bis-methoxymethoxyphenyl)propenoate 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 48.33h， 生成 5,7,3',4'-tetrahydroxy-5'-methoxyflavone,
  参考文献：
  名称：

  Synthesis and Structures of Regioisomeric Hydnocarpin-Type Flavonolignans

  摘要：

  Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.

  DOI：

  10.1021/np000166d
• 作为产物：
  描述：

  3,4-二羟基-5-甲氧基苯甲醛 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 17.25h， 生成 1-(2-hydroxy-4,6-bismethoxymethoxyphenyl)-3-(3-methoxy-4,5-bis-methoxymethoxyphenyl)propenoate
  参考文献：
  名称：

  Synthesis and Structures of Regioisomeric Hydnocarpin-Type Flavonolignans

  摘要：

  Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.

  DOI：

  10.1021/np000166d