4-[3-hydroxy-2-(2-methoxyphenoxy)prop-1-enyl]-2,6-dimethoxyphenol | 92444-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-[3-hydroxy-2-(2-methoxyphenoxy)prop-1-enyl]-2,6-dimethoxyphenol
• CAS: 92444-02-5
• 化学式: C₁₈H₂₀O₆
• 分子量: 332.353
• InChiKey: KSGZYKOSFPLIDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[3-hydroxy-2-(2-methoxyphenoxy)prop-1-enyl]-2,6-dimethoxyphenol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2-methoxyphenoxy)prop-2-enal
  参考文献：
  名称：

  Cross-Coupling of Hydroxycinnamyl Aldehydes into Lignins

  摘要：

  [GRAPHICS]Pathways for hydroxycinnamyl aldehyde incorporation into lignins are revealed by examining transgenic plants deficient in cinnamyl alcohol dehydrogenase, the enzyme that converts hydroxycinnamyl aldehydes to the hydroxycinnamyl alcohol lignin monomers. In such plants the aldehydes incorporate into lignins via radical coupling reactions. As diagnostically revealed by long-range C-13-H-1 correlative NMR, sinapyl aldehyde (3,5-dimethoxy 4-hydroxy-cinnamaldehyde) 8-O-4-cross-couples with both gualacyl (3-methoxy-4-hydroxyphenyl-propanoid) and syringyl (3,5-dimethoxy-4-hydroxyphenyl-propanoid) units, whereas coniferyl aldehyde cross-couples only with syringyl units.

  DOI：

  10.1021/ol005906o
• 作为产物：
  描述：

  2-甲氧基苯氧基乙酸乙酯 在 三甲基溴硅烷 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 4-[3-hydroxy-2-(2-methoxyphenoxy)prop-1-enyl]-2,6-dimethoxyphenol
  参考文献：
  名称：

  Cross-Coupling of Hydroxycinnamyl Aldehydes into Lignins

  摘要：

  [GRAPHICS]Pathways for hydroxycinnamyl aldehyde incorporation into lignins are revealed by examining transgenic plants deficient in cinnamyl alcohol dehydrogenase, the enzyme that converts hydroxycinnamyl aldehydes to the hydroxycinnamyl alcohol lignin monomers. In such plants the aldehydes incorporate into lignins via radical coupling reactions. As diagnostically revealed by long-range C-13-H-1 correlative NMR, sinapyl aldehyde (3,5-dimethoxy 4-hydroxy-cinnamaldehyde) 8-O-4-cross-couples with both gualacyl (3-methoxy-4-hydroxyphenyl-propanoid) and syringyl (3,5-dimethoxy-4-hydroxyphenyl-propanoid) units, whereas coniferyl aldehyde cross-couples only with syringyl units.

  DOI：

  10.1021/ol005906o