3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-8-methoxy-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-8-methoxy-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde
• 英文别名: 2-(4-Hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydro-1,4-benzodioxine-7-carbaldehyde
• 化学式: C₁₈H₁₈O₇
• 分子量: 346.337
• InChiKey: VWSIKPBSEBLQSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  氯甲基甲基醚 、 3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-8-methoxy-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde 在 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以85%的产率得到2-hydroxymethyl-8-methoxy-3-(3-methoxy-4-methoxymethoxyphenyl)-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde
  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 、 反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 在 silver carbonate 作用下， 以 丙酮 、 苯 为溶剂， 反应 7.0h， 以36%的产率得到3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-8-methoxy-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde
  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

文献信息

• Synthesis and Structures of Regioisomeric Hydnocarpin-Type Flavonolignans
  作者：Nathan R. Guz、Frank R. Stermitz

  DOI：10.1021/np000166d

  日期：2000.8.1

  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.