(1S,3R,4R,6R)-4-iodo-7,7-dimethylspiro[bicyclo[4.1.0]heptane-3,5'-oxolane]-2'-one | 477841-56-8

• 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,3R,4R,6R)-4-iodo-7,7-dimethylspiro[bicyclo[4.1.0]heptane-3,5'-oxolane]-2'-one
• CAS: 477841-56-8
• 化学式: C₁₂H₁₇IO₂
• 分子量: 320.17
• InChiKey: GYSYMLYSYVHNDB-JXVAYASWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,6R)-4-iodo-7,7-dimethylspiro[bicyclo[4.1.0]heptane-3,5'-oxolane]-2'-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以67%的产率得到(1R,4R,6S)-7,7-dimethylspiro[bicyclo[4.1.0]hept-2-ene-4,5'-oxolane]-2'-one
  参考文献：
  名称：

  Lactones. Part 15: Synthesis of chiral spirolactones with a carane system—insect feeding deterrents

  摘要：

  Starting from (+)-3-carene 1 several spirolactones with carane backbone were synthesized. delta-Hydroxy-gamma-lactone 5 was obtained by acidic lactonization of a gamma,delta-epoxy ester. Iodolactone 8 and bromolactone 9 were products of iodolactonization of gamma,delta-unsaturated acid 7 and bromolactonization of gamma,delta-unsaturated ester 3 respectively. The halo lactones were subjected to reductive dehalogenation with tributyltin hydride and dehydrohalogenation with DBU. The structures of the lactones obtained were confirmed by X-ray analysis and spectral data. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00476-7
• 作为产物：
  描述：

  (+)-3-[(1S,6R)-7,7-dimethylbicyclo[4.1.0]hept-3-en-3-yl]propanoic acid 在 碳酸氢钠 、 碘 、 potassium iodide 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以65%的产率得到(1S,3R,4R,6R)-4-iodo-7,7-dimethylspiro[bicyclo[4.1.0]heptane-3,5'-oxolane]-2'-one
  参考文献：
  名称：

  Lactones. Part 15: Synthesis of chiral spirolactones with a carane system—insect feeding deterrents

  摘要：

  Starting from (+)-3-carene 1 several spirolactones with carane backbone were synthesized. delta-Hydroxy-gamma-lactone 5 was obtained by acidic lactonization of a gamma,delta-epoxy ester. Iodolactone 8 and bromolactone 9 were products of iodolactonization of gamma,delta-unsaturated acid 7 and bromolactonization of gamma,delta-unsaturated ester 3 respectively. The halo lactones were subjected to reductive dehalogenation with tributyltin hydride and dehydrohalogenation with DBU. The structures of the lactones obtained were confirmed by X-ray analysis and spectral data. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00476-7