(1S,3S)-(-)-trans-chrysanthemol | 76704-87-5

• 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: (1S,3S)-(-)-trans-chrysanthemol
• 英文别名: trans-Chrysanthemumalkohol；trans-Chrysanthemylalkohol；cis-Chrysanthemumalkohol；trans-Chrysanthemol；[(1S,3S)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methanol
• CAS: 76704-87-5
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: HIPIENNKVJCMAP-IUCAKERBSA-N

物化性质

• 保留指数：
  1163.4

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  菊酸乙酯 在 氢氧化钾 、 lithium aluminium tetrahydride 、 potassium 2-methylbutan-2-olate 作用下， 以 乙醚 为溶剂， 生成 (1S,3S)-(-)-trans-chrysanthemol
  参考文献：
  名称：

  Electron Transfer Photochemistry of Chrysanthemol:  An Intramolecular S_N2‘ Reaction of a Vinylcyclopropane Radical Cation

  摘要：

  The electron transfer photochemistry of optically pure (1R,3S)-(f)-cis-chrysanthemol (cis-2) results in the formation of (R)-5-(1-(p-cyanophenyl)-1-methyethyl)-2,2-dimethyl oxacyclohex-3-ene (4) with significant retention of optical activity. The product is rationalized via nucleophilic attack of the alcoholic function of the radical cation on the terminal carbon of the vinyl group with simultaneous replacement of an isopropyl radical as an intramolecular leaving group in an apparent S(N)2' reaction. This mode of attack is unprecedented in vinylcyclopropane radical cations and is interpreted as evidence for the significant role that relief of ring strain and its avoidance play in determining the course of nucleophilic capture in radical cationic systems.

  DOI：

  10.1021/ja953596c

文献信息

• US4521331A
  申请人：——

  公开号：US4521331A

  公开（公告）日：1985-06-04