(1S,2R,4S)-2-(2-bromo-5-fluorophenoxy)-1,7,7-trimethylbicyclo[2.2.1]heptane | 1036724-60-3

• 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,2R,4S)-2-(2-bromo-5-fluorophenoxy)-1,7,7-trimethylbicyclo[2.2.1]heptane
• CAS: 1036724-60-3
• 化学式: C₁₆H₂₀BrFO
• 分子量: 327.237
• InChiKey: SWMILBWAZCVHHH-DRZCJDIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-2,4-二氟苯 、 冰片 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 (1S,2R,4S)-2-(2-bromo-5-fluorophenoxy)-1,7,7-trimethylbicyclo[2.2.1]heptane 、 (1S,2R,4S)-2-(4-bromo-3-fluorophenoxy)-1,7,7-trimethylbicyclo[2.2.1]heptane
  参考文献：
  名称：

  Regioselectivity of fluorine substitution by alkoxides on unsymmetrical difluoroarenes

  摘要：

  An efficient approach to unsymmetrical halogenated resorcinol diethers has been developed. This synthesis consists of two subsequent nucleophilic aromatic substitutions (S(N)Ar) of unsymmetrical difluoroarenes by alkoxides. The novelty of this approach is its control of regioselectivity during the first SNAr, which occurs at room temperature. Interestingly, the reactivity of competing fluorines was correlated to their chemical shift in (19)F NMR. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.091