(+)-lariciresinol | 1350444-48-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (+)-lariciresinol
• 英文别名: 4-[[(3S,4R,5R)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
• CAS: 1350444-48-2
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: MHXCIKYXNYCMHY-SIFCLUCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (7R,8R,8'S)-4,4'-dibenzyloxy-3,3'-dimethoxy-7,9'-epoxylignan-9-ol 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (+)-lariciresinol
  参考文献：
  名称：

  Stereoselective Syntheses of All Stereoisomers of Lariciresinol and Their Plant Growth Inhibitory Activities

  摘要：

  All stereoisomers of lariciresinol were synthesized to examine the effect of stereochemistry on plant growth. Configuration of benzylic 7-positions was constructed through S(N)1 or S(N)2 intramolecular etherification. 8- and 8'-position configurations were established from the starting material except for all cis stereoisomers, the 8-position configurations of which were achieved by employing stereoselective hydroboration. (-)-Lariciresinol and its 7S,8S,8'R stereoisomer inhibited the root growth of Italian ryegrass to 51-55% relative to the negative control, whereas other stereoisomers had less effect. These results demonstrate that the stereochemistry of lignans is one of the important factors influencing their inhibitory activity.

  DOI：

  10.1021/jf203222w