[(1R,4aR,7S,7aS)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] acetate | 861659-40-7

• 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: [(1R,4aR,7S,7aS)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] acetate
• CAS: 861659-40-7
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: UVHMHLNMYIOYOX-ZZKLTDFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酸酐 、 cis,cis-Nepetalactol 在 二异丁基氢化铝 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 正己烷 为溶剂， 反应 0.5h， 生成 [(1S,4aR,7S,7aS)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] acetate 、 [(1R,4aR,7S,7aS)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] acetate
  参考文献：
  名称：

  Simplified Isolation Procedure and Interconversion of the Diastereomers of Nepetalactone and Nepetalactol

  摘要：

  Three nepetalactones were isolated from Nepeta racemosa (mussinii) by traditional methods. An improved method was developed to isolate nepetalactones from N. faassenii. An epimerization procedure was used to prepare the fourth 7S-nepetalactone diastereomer. The cis-fused nepetalactols were prepared by reduction of the corresponding nepetalactones, while the trans-fused nepetalactols were unstable and found to undergo ring-opening reactions yielding iridodials. The characterizations and structural assignments by means of NMR agree with quantum chemical density functional calculations.

  DOI：

  10.1021/np049647d

文献信息

• Simplified Isolation Procedure and Interconversion of the Diastereomers of Nepetalactone and Nepetalactol
  作者：Ilme Liblikas、Ellen M. Santangelo、Johan Sandell、Peter Baeckström、Mats Svensson、Ulla Jacobsson、C. Rikard Unelius

  DOI：10.1021/np049647d

  日期：2005.6.1

  Three nepetalactones were isolated from Nepeta racemosa (mussinii) by traditional methods. An improved method was developed to isolate nepetalactones from N. faassenii. An epimerization procedure was used to prepare the fourth 7S-nepetalactone diastereomer. The cis-fused nepetalactols were prepared by reduction of the corresponding nepetalactones, while the trans-fused nepetalactols were unstable and found to undergo ring-opening reactions yielding iridodials. The characterizations and structural assignments by means of NMR agree with quantum chemical density functional calculations.