β-apopicropodophyllol | 104720-04-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: β-apopicropodophyllol
• 英文别名: [(5R)-6-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,8-dihydrobenzo[f][1,3]benzodioxol-7-yl]methanol
• CAS: 104720-04-9
• 化学式: C₂₂H₂₄O₇
• 分子量: 400.428
• InChiKey: POYHFBKBTMAQRC-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  β-apopicropodophyllol 在 吡啶 、 盐酸 、 sodium hydride 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 66.5h， 生成 (R)-7-Oxo-9-(3,4,5-trimethoxy-phenyl)-6,7,8,9-tetrahydro-5H-1,3-dioxa-dicyclopenta[b,g]naphthalene-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Anjanamurthy, C.; Rai, K. M. Lokanath, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 131 - 135

  摘要：

  DOI：
• 作为产物：
  描述：

  beta-Apopicropodophyllin 在 lithium aluminium tetrahydride 、 盐酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 15.5h， 以47%的产率得到β-apopicropodophyllol
  参考文献：
  名称：

  Structure–activity relationship of chemical defenses from the freshwater plant Micranthemum umbrosum

  摘要：

  Vascular plants produce a variety of molecules of phenylpropanoid biosynthetic origin, including lignoids. Recent investigations indicated that in freshwater plants, some of these natural products function as chemical defenses against generalist consumers such as crayfish. Certain structural features are shared among several of these anti-herbivore compounds, including phenolic, methoxy, methylenedioxy, and lactone functional groups. To test the relative importance of various functional groups in contributing to the feeding deterrence of phenylpropanoid-based natural products, we compared the feeding behavior of crayfish offered artificial diets containing analogs of elemicin (1) and beta-apopicropodophyllin (2), chemical defenses of the freshwater macrophyte Micranthemum umbrosum. Both allyl and methoxy moieties of 1 contributed to feeding deterrence. Disruption of the lactone moiety of 2 reduced its deterrence. Finally, feeding assays testing effects of 1 and 2 at multiple concentrations established that these two natural products interact additively in deterring crayfish feeding. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2006.05.007