(10R)-3,14-didehydro-10-hydroxy-ginkgolide | 148637-23-4

• 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: (10R)-3,14-didehydro-10-hydroxy-ginkgolide
• 英文别名: ginkgolide L；anhydroginkgolide A
• CAS: 148637-23-4
• 化学式: C₂₀H₂₂O₈
• 分子量: 390.39
• InChiKey: NFDZKHCIMGCVNP-KVBXQQANSA-N

物化性质

• 沸点：
  687.9±55.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  28.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (10R)-3,14-didehydro-10-hydroxy-ginkgolide 在 Crabtree's catalyst 氢气 作用下， 20.0 ℃ 、506.66 kPa 条件下， 以80%的产率得到
  参考文献：
  名称：

  A Concise Synthesis of Ginkgolide M, a Minor Component of a Terpene Trilactone Fraction from Ginkgo biloba Roots

  摘要：

  Ginkgolide M (GM), which is found only in the roots of the Ginkgo biloba tree and is an inhibitor of ligand-operated ion channels in the central nervous system, has been prepared in three steps from 10-benzylginkgolide C, an intermediate generated during the isolation and separation of ginkgolides from Ginkgo biloba leaf extract. The described synthetic sequence can be applied to access GM derivatives for biological studies.

  DOI：

  10.1021/np050403i
• 作为产物：
  描述：

  ginkgolide A 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(10R)-3,14-didehydro-10-hydroxy-ginkgolide
  参考文献：
  名称：

  A Concise Synthesis of Ginkgolide M, a Minor Component of a Terpene Trilactone Fraction from Ginkgo biloba Roots

  摘要：

  Ginkgolide M (GM), which is found only in the roots of the Ginkgo biloba tree and is an inhibitor of ligand-operated ion channels in the central nervous system, has been prepared in three steps from 10-benzylginkgolide C, an intermediate generated during the isolation and separation of ginkgolides from Ginkgo biloba leaf extract. The described synthetic sequence can be applied to access GM derivatives for biological studies.

  DOI：

  10.1021/np050403i

文献信息

• Chemistry of the Ginkgolides. Part 10: Access to 14C-Labelled Ginkgolide A
  作者：Klaus Weinges、Hartmut Schick、Hermann Irngartinger、Thomas Oeser

  DOI：10.1016/s0040-4020(00)00230-1

  日期：2000.5

  In four reaction steps, ginkgolide A (1) was synthesized from the enol-acetate 3, which is available in six steps from 1. The key step was the reaction of the ol-epoxy-acetate 4 with the lithium enolate of methyl propionate to give the compounds 5 and 6. C-14-Labelled ginkgolide A, which is of interest for pharmacological studies, can be synthesized using the C-14-labelled methyl propionate. (C) 2000 Elsevier Science Ltd. All rights reserved.