13-bromo-8-methoxy<2.2>metacyclophane | 137594-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 13-bromo-8-methoxy<2.2>metacyclophane
• 英文别名: 6-Bromo-16-methoxytricyclo[9.3.1.14,8]hexadeca-1(15),4(16),5,7,11,13-hexaene
• CAS: 137594-37-7
• 化学式: C₁₇H₁₇BrO
• 分子量: 317.225
• InChiKey: NEPBWOYDUPGZAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  8-methoxy<2.2>metacyclophane 在 benzyltrimethylammonium tribromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以32.0%的产率得到2-bromo-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

文献信息

• Medium-sized cyclophanes. 2. Bromination of 8-methoxy[2.2]metacyclophanes
  作者：Takehiko Yamato、Seiji Ide、Kiwamu Tokuhisa、Masashi Tashiro

  DOI：10.1021/jo00027a048

  日期：1992.1

  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.