(Z)-2-[2-[(1S,4aR,5S,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]but-2-ene-1,4-diol | 40433-83-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (Z)-2-[2-[(1S,4aR,5S,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]but-2-ene-1,4-diol
• CAS: 40433-83-8
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: FUHGIRXMYOFRFO-BFLVOBETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-[2-[(1S,4aR,5S,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]but-2-ene-1,4-diol 在 jones reagent 、 Celite 、 silver carbonate 作用下， 以 丙酮 、 苯 为溶剂， 反应 7.0h， 生成 ent-Labda-8(17),13-dien-19-oic acid-15,16-olide
  参考文献：
  名称：

  In Vitro Platelet-Activating Factor Receptor Binding Inhibitory Activity of Pinusolide Derivatives: A Structure−Activity Study

  摘要：

  Pinusolide, a labdane-type diterpene lactone isolated from Biota orientalis, was found to be a potent platelet-activating factor (PAF) receptor binding antagonist. To investigate the structure-activity relationship and find derivatives with improved pharmacological profiles, 17 pinusolide derivatives were prepared and tested for their ability to inhibit the PAF receptor binding. The results demonstrated that the carboxymethyl ester group at C-19, the integrity of the alpha,beta-unsaturated butenolide ring, and the exocyclic olefinic function of pinusolide are all necessary for its maximum PAF receptor binding inhibitory activity. Among the derivatives, the 17-nor-8-oxo derivative 8 was found to be as potent as pinusolide. The results also suggested that several derivatives warrant further pharmaceutical and pharmacological studies due to their improved water solubility (8 and 11) and apparent lack of susceptibility to Michael-type nucleophilic addition (13 and 18).

  DOI：

  10.1021/jm970569j
• 作为产物：
  描述：

  红松内酯 在 lithium aluminium tetrahydride 作用下， 生成 (Z)-2-[2-[(1S,4aR,5S,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]but-2-ene-1,4-diol
  参考文献：
  名称：

  Pinusolide, a new diterpenoid from Pinus sibirica and P. korsensis

  摘要：

  DOI：

  10.1007/bf00563440