((3aR,5aS,8aS)-1-Methylene-5-oxo-1,2,3,3a-tetrahydro-6H-dicyclopenta[b,c]furan-5a-yloxy)-acetic acid | 137538-08-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ((3aR,5aS,8aS)-1-Methylene-5-oxo-1,2,3,3a-tetrahydro-6H-dicyclopenta[b,c]furan-5a-yloxy)-acetic acid
• 英文别名: 2-[[(1S,5R,8S)-2-methylidene-7-oxo-6-oxatricyclo[6.3.0.01,5]undec-10-en-8-yl]oxy]acetic acid
• CAS: 137538-08-0
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: WETCRBACOUDYSY-JIMOISOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((3aR,5aS,8aS)-1-Methylene-5-oxo-1,2,3,3a-tetrahydro-6H-dicyclopenta[b,c]furan-5a-yloxy)-acetic acid 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 苯 为溶剂， 反应 3.0h， 以76%的产率得到(2aS,3aS,6aS,7R,9aS)-8,9-dihydro-1H,4H,7H-7,3a-(epoxymethano)cyclobuta[b]dicyclopenta[c,d]furan-2,11(2aH)-dione
  参考文献：
  名称：

  Enantioselective total synthesis of ginkgolide derivatives lacking the tert-butyl group, an essential structural subunit for antagonism of platelet activating factor

  摘要：

  An enantioselective total synthesis of the ginkgolide B analog 3 is reported along with the results of bioassays for antagonism of platelet activating factor. The three orders of magnitude difference in bioactivity of 2 and 3 demonstrates that the tert-butyl group of the ginkgolides is essential for anti-PAF potency.

  DOI：

  10.1016/s0040-4039(00)92265-2
• 作为产物：
  描述：

  (3aR,5aS,8aS)-5a-Hydroxy-1-methylene-1,2,3,3a,5a,6-hexahydro-dicyclopenta[b,c]furan-5-one 在 双(三甲基硅烷基)氨基钾 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 44.5h， 生成 ((3aR,5aS,8aS)-1-Methylene-5-oxo-1,2,3,3a-tetrahydro-6H-dicyclopenta[b,c]furan-5a-yloxy)-acetic acid
  参考文献：
  名称：

  Enantioselective total synthesis of ginkgolide derivatives lacking the tert-butyl group, an essential structural subunit for antagonism of platelet activating factor

  摘要：

  An enantioselective total synthesis of the ginkgolide B analog 3 is reported along with the results of bioassays for antagonism of platelet activating factor. The three orders of magnitude difference in bioactivity of 2 and 3 demonstrates that the tert-butyl group of the ginkgolides is essential for anti-PAF potency.

  DOI：

  10.1016/s0040-4039(00)92265-2