1-bromo-2-methoxy-4,5,9,10-tetrahydropyrene | 137594-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-bromo-2-methoxy-4,5,9,10-tetrahydropyrene
• CAS: 137594-47-9
• 化学式: C₁₇H₁₅BrO
• 分子量: 315.209
• InChiKey: SKMCJFMUWZRTRK-UHFFFAOYSA-N

物化性质

• 沸点：
  432.4±45.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  甲醇 、 8-methoxy-5-tert-butyl<2.2>-metacyclophane 在 benzyltrimethylammonium tribromide 作用下， 反应 0.08h， 以92%的产率得到1-bromo-2-methoxy-4,5,9,10-tetrahydropyrene
  参考文献：
  名称：

  Medium-sized cyclophanes. 2. Bromination of 8-methoxy[2.2]metacyclophanes

  摘要：

  When 8-methoxy[2.2]metacyclophanes 5 are treated with benzyl trimethylammonium tribromide in dichloromethane, the transannular reaction products, tetrahydropyrene 6 and 7 are obtained along with 5-bromo-8-methoxy[2.2]metacyclophanes 8. The bromination of 5-tert-butyl-8-methoxy[2.2]metacyclophanes 9a-9g in dichloromethane is carried out under the same conditions to afford tetrahydropyrene derivatives exclusively. On the other hand, when the bromination reactions are performed in various alcohols, alkoxy-substituted tetrahydropyrenes 11 and 12 are obtained in good yields, which are easily dehydrogenated with DDQ to afford the corresponding pyrene derivatives. The reaction mechanisms of the above reactions are also discussed.

  DOI：

  10.1021/jo00027a048