(3R,7R)-9,13-dimethyl-6-oxatricyclo[8.3.0.0^3,7]tetradecan-9,13-dien-5,12-dione | 1006369-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,7R)-9,13-dimethyl-6-oxatricyclo[8.3.0.0^3,7]tetradecan-9,13-dien-5,12-dione
• 英文别名: (3aR,9aR)-5,8-dimethyl-1,3a,4,6,9,9a-hexahydroazuleno[6,5-b]furan-2,7-dione
• CAS: 1006369-99-8
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: NMZQXHBMMBCWSG-NOZJJQNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,7R)-9,13-dimethyl-6-oxatricyclo[8.3.0.0^3,7]tetradecan-9,13-dien-5,12-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 (3R,7R,9R,10R)-9,13-dimethyl-6-oxatricyclo[8.3.0.0^3,7]tetradec-13-en-5,12-dione 、 (3R,7R,9S,10S)-9,13-dimethyl-6-oxatricyclo[8.3.0.0^3,7]tetradec-13-en-5,12-dione
  参考文献：
  名称：

  Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson−Khand-Type Reaction

  摘要：

  [GRAPHICS]The first total synthesis of (+)-achalensolide was achieved from a commercially available D-(-)-isoascorbic acid. The known epoxide, derived from D-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.

  DOI：

  10.1021/jo702330y
• 作为产物：
  描述：

  在 chromium(VI) oxide 、 硫酸 、 水 作用下， 以 丙酮 为溶剂， 以23.9 mg的产率得到(3R,7R)-9,13-dimethyl-6-oxatricyclo[8.3.0.0^3,7]tetradecan-9,13-dien-5,12-dione
  参考文献：
  名称：

  Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson−Khand-Type Reaction

  摘要：

  [GRAPHICS]The first total synthesis of (+)-achalensolide was achieved from a commercially available D-(-)-isoascorbic acid. The known epoxide, derived from D-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.

  DOI：

  10.1021/jo702330y