(4R*,5S*)-4,5-(1,1-cyclohexylidenedioxy)-1-cyclohexene | 180624-64-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R*,5S*)-4,5-(1,1-cyclohexylidenedioxy)-1-cyclohexene
• 英文别名: (3aS,7aR)-spiro[3a,4,7,7a-tetrahydro-1,3-benzodioxole-2,1'-cyclohexane]
• CAS: 180624-64-0
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: OUVNMNLUOBQTNV-PHIMTYICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R*,5S*)-4,5-(1,1-cyclohexylidenedioxy)-1-cyclohexene 在 二氯二茂钛 、 lithium aluminium tetrahydride 、 碳酸氢钠 、 臭氧 、 bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 86.0h， 生成 5-(Iodomethyl)spiro[3a,4,5,7,8,8a-hexahydro-[1,3]dioxolo[4,5-d]oxepine-2,1'-cyclohexane]
  参考文献：
  名称：

  Preparation of Oxepanes, Oxepenes, and Oxocanes by Iodoetherification using Bis(sym-collidine)iodine(I) Hexafluorophosphate as Electrophile

  摘要：

  Oxepanes have been obtained in good yields (40-95%) by iodoetherification of unsaturated alcohols using bis(sym-collidine)iodine(I) hexafluorophosphate (1) as electrophile, either by 7-exo-mode or 7-endo-mode cyclizations. 4-Oxepenes could also be formed from 4,6-heptadien-1-ols; the presence of a substituent on the carbon 6 appeared necessary, while for steric reasons the presence of a substituent on the carbon 7 was unfavorable. Oxocanes could be obtained in moderate yields (18-27%).

  DOI：

  10.1021/jo960506t
• 作为产物：
  描述：

  1,4-环己二烯 、 alkaline earth salt of/the/ methylsulfuric acid 在 四氧化锇 、 水 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 (4R*,5S*)-4,5-(1,1-cyclohexylidenedioxy)-1-cyclohexene
  参考文献：
  名称：

  Preparation of Oxepanes, Oxepenes, and Oxocanes by Iodoetherification using Bis(sym-collidine)iodine(I) Hexafluorophosphate as Electrophile

  摘要：

  Oxepanes have been obtained in good yields (40-95%) by iodoetherification of unsaturated alcohols using bis(sym-collidine)iodine(I) hexafluorophosphate (1) as electrophile, either by 7-exo-mode or 7-endo-mode cyclizations. 4-Oxepenes could also be formed from 4,6-heptadien-1-ols; the presence of a substituent on the carbon 6 appeared necessary, while for steric reasons the presence of a substituent on the carbon 7 was unfavorable. Oxocanes could be obtained in moderate yields (18-27%).

  DOI：

  10.1021/jo960506t