4-endo-8-exo-bis-(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one | 3810-34-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 4-endo-8-exo-bis-(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one
• 英文别名: 4-trans,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one；2-exo,6-endo-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-8-one；2-exo,6-endo-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-8-one
• CAS: 3810-34-2；66288-89-9；92216-40-5；92216-41-6；125638-31-5；125638-32-6；148554-51-2；148554-52-3；148554-53-4
• 化学式: C₂₀H₂₀O₇
• 分子量: 372.375
• InChiKey: JOVBAVJQHJYOID-OZOSWLFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  94.45
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  4-苄氧基-3-甲氧基苯甲醛 在 palladium on activated charcoal 二甲基硫 、 硼烷 、 氢气 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 4-endo-8-exo-bis-(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one
  参考文献：
  名称：

  Stevens, David R.; Till, Clive P.; Whiting, Donald A., Journal of the Chemical Society. Perkin transactions I, 1992, # 2, p. 185 - 190

  摘要：

  DOI：

文献信息

• Lignin–feruloyl ester cross-links in grasses. Part 2. Model compound syntheses
  作者：John Ralph、Richard F. Helm、Stéphane Quideau

  DOI：10.1039/p19920002971

  日期：——

  single geometrical isomer was produced. Synthesis of both isomers of derived compounds and detailed NMR analysis indicated that this was the expected Z-isomer. A model for β-5 coupled products, 3-[3-carboxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-5-yl]acrylic acid bis(methyl 5-deoxy-α-L-arabinofuranosid-5-yl) ester, was obtained as a cis/trans mixture in 55% yield by radical coupling

  已经合成了五种模拟当阿魏酸酯共聚成木质素时产生的各种结构的化合物。这些模型代表了被认为存在于禾本科中但尚未分离的木质素-阿魏酸酯-多糖结构。完整的光谱表征可提供重要的化学位移信息，以帮助鉴定天然木质素和合成DHP聚合物中的这些键。甲基5- O- 4 - O- [3-羟基-1-（4-羟基-3-甲氧基苯基）-2-（2-甲氧基苯氧基）丙基]阿魏酰} -α - L-阿拉伯呋喃糖苷，α模型阿魏酸酯与木质素的α-键连接，是苏式和赤式的混合物通过将甲基5- O-（E）-阿魏酰基-α- L-阿拉伯呋喃糖苷（FA-Ara）添加到衍生自1-（4-羟基-3-甲氧基苯基）-2-（2-甲氧基苯氧基）的醌甲基化物中的异构体丙烷-1,3-二醇（愈创木脂甘油-β-愈创木脂醚）。甲基5- O- 4 - O- [2-羟基-2-（4-羟基-3-甲氧基-苯基）-1-（羟甲基）乙基]阿魏酰基}-α- L-呋喃糖呋喃糖苷，一种β
• Velde, Vincent Vande; Lavie, David; Gottlieb, Hugo E., Journal of the Chemical Society. Perkin transactions I, 1984, # 6, p. 1159 - 1164
  作者：Velde, Vincent Vande、Lavie, David、Gottlieb, Hugo E.、Perold, Guido W.、Scheinmann, Feodor

  DOI：——

  日期：——
• 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.