Methanesulfonic acid (1R,2S,3R,4R,7R)-7-bromomethyl-3-(2,6-dimethoxy-4-pentyl-phenyl)-1,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester | 140633-49-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: Methanesulfonic acid (1R,2S,3R,4R,7R)-7-bromomethyl-3-(2,6-dimethoxy-4-pentyl-phenyl)-1,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
• 英文别名: [(1R,2S,3R,4R,7R)-7-(bromomethyl)-3-(2,6-dimethoxy-4-pentylphenyl)-1,7-dimethyl-2-bicyclo[2.2.1]heptanyl] methanesulfonate
• CAS: 140633-49-4
• 化学式: C₂₄H₃₇BrO₅S
• 分子量: 517.525
• InChiKey: AYGOWHMFAHLSLP-NEMWVAFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (1R,2S,3R,4R,7R)-7-bromomethyl-3-(2,6-dimethoxy-4-pentyl-phenyl)-1,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 在 四乙二醇二甲醚 、 sodium naphthalenide 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到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 吡啶 、 4-二甲氨基吡啶 、 copper(l) iodide 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 19.08h， 生成 Methanesulfonic acid (1R,2S,3R,4R,7R)-7-bromomethyl-3-(2,6-dimethoxy-4-pentyl-phenyl)-1,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
  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