1,4-bis(4-hydroxy-3-methoxyphenyl)butadiene

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,4-bis(4-hydroxy-3-methoxyphenyl)butadiene
• 英文别名: 4-[(1E,3E)-4-(4-hydroxy-3-methoxyphenyl)buta-1,3-dienyl]-2-methoxyphenol
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: KKBPAPCYIJKREN-GGWOSOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  阿魏酸 在 锂硼氢 、 氧气 、 三氯化铁 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 1,4-bis(4-hydroxy-3-methoxyphenyl)butadiene
  参考文献：
  名称：

  Synthesis of 4,8-bis(4-hydroxy-3-methoxyphenyl )-3,7-dioxabicyclo[3.3.0]octan-2-ones and determination of their relative configuration via long-range proton couplings

  摘要：

  A short synthesis of the furofuranoid lignan, 4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-2-one (MEL), was accomplished via a simple regioselective hydride reduction of the dilactone parent [4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione], followed by deoxygenation of the lactone-lactol intermediate via silane hydride transfer. The 4-trans-8-cis(iso-MEL) and the 4-cis-8-trans(epi-MEL) isomers, and a fourth related compound, featuring a 3-fused 5-membered ring skeleton were additionally formed. All four compounds were fully characterized by use of 1D and 2D NMR techniques. Examination of the long-range coupled proton network by delayed COSY experiments allowed determination of the relative configuration of these 4,8-diaryl-3,7-dioxabicyclo[3.3.0]octan-2-one structures. The pathways followed by these long-range proton couplings and implications of the long-range and vicinal couplings with respect to favoured conformations are discussed.

  DOI：

  10.1039/p19930000653

文献信息

• Synthesis of 4,8-bis(4-hydroxy-3-methoxyphenyl )-3,7-dioxabicyclo[3.3.0]octan-2-ones and determination of their relative configuration via long-range proton couplings
  作者：St�phane Quideau、John Ralph

  DOI：10.1039/p19930000653

  日期：——

  A short synthesis of the furofuranoid lignan, 4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-2-one (MEL), was accomplished via a simple regioselective hydride reduction of the dilactone parent [4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione], followed by deoxygenation of the lactone-lactol intermediate via silane hydride transfer. The 4-trans-8-cis(iso-MEL) and the 4-cis-8-trans(epi-MEL) isomers, and a fourth related compound, featuring a 3-fused 5-membered ring skeleton were additionally formed. All four compounds were fully characterized by use of 1D and 2D NMR techniques. Examination of the long-range coupled proton network by delayed COSY experiments allowed determination of the relative configuration of these 4,8-diaryl-3,7-dioxabicyclo[3.3.0]octan-2-one structures. The pathways followed by these long-range proton couplings and implications of the long-range and vicinal couplings with respect to favoured conformations are discussed.