(1R,2S,3R,4R,7R)-7-Bromomethyl-3-(2,6-dimethoxy-4-pentyl-phenyl)-1,7-dimethyl-bicyclo[2.2.1]heptan-2-ol | 140633-50-7

• 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,2S,3R,4R,7R)-7-Bromomethyl-3-(2,6-dimethoxy-4-pentyl-phenyl)-1,7-dimethyl-bicyclo[2.2.1]heptan-2-ol
• 英文别名: (1R,2S,3R,4R,7R)-7-(bromomethyl)-3-(2,6-dimethoxy-4-pentylphenyl)-1,7-dimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 140633-50-7
• 化学式: C₂₃H₃₅BrO₃
• 分子量: 439.433
• InChiKey: IGPVYMHGYRPBPK-FFROMMOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4R,7R)-7-Bromomethyl-3-(2,6-dimethoxy-4-pentyl-phenyl)-1,7-dimethyl-bicyclo[2.2.1]heptan-2-ol 在 吡啶 、 4-二甲氨基吡啶 、 四乙二醇二甲醚 、 sodium naphthalenide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.25h， 生成 1,3-二甲氧基-2-[(1R,6R)-3-甲基-6-丙-1-烯-2-基-1-环己-2-烯基]-5-戊基苯
  参考文献：
  名称：

  A one-step method for the .alpha.-arylation of camphor. Synthesis of (-)-cannabidiol and (-)-cannabidiol dimethyl ether.

  摘要：

  The syntheses of (-)-cannabidiol and (-)-cannabidiol dimethyl ether were accomplished via fragmentation of an appropriately substituted 9-bromocamphor derivative. A new method of alpha-arylation of 3,9-dibromocamphor was shown to provide a variety of alpha-arylated camphor derivatives in good yields.

  DOI：

  10.1021/jo00039a022
• 作为产物：
  描述：

  (2,6-dimethoxy-4-pentylphenyl)lithium 在 copper(l) iodide 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.08h， 生成 (1R,2S,3R,4R,7R)-7-Bromomethyl-3-(2,6-dimethoxy-4-pentyl-phenyl)-1,7-dimethyl-bicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  A one-step method for the .alpha.-arylation of camphor. Synthesis of (-)-cannabidiol and (-)-cannabidiol dimethyl ether.

  摘要：

  The syntheses of (-)-cannabidiol and (-)-cannabidiol dimethyl ether were accomplished via fragmentation of an appropriately substituted 9-bromocamphor derivative. A new method of alpha-arylation of 3,9-dibromocamphor was shown to provide a variety of alpha-arylated camphor derivatives in good yields.

  DOI：

  10.1021/jo00039a022