2,7-di-tert-butyl-4,5,9,10-tetrahydropyrene | 69080-03-1

• 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: 2,7-di-tert-butyl-4,5,9,10-tetrahydropyrene
• 英文别名: 2,7-di-t-butyl-4,5,9,10-tetrahydropyrene；2,7-Di-tert-butyl-4,5,9,10-tetrahydro-pyren；2,7-ditert-butyl-4,5,9,10-tetrahydropyrene
• CAS: 69080-03-1
• 化学式: C₂₄H₃₀
• 分子量: 318.502
• InChiKey: MZIUQNAUHJDZTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,7-di-tert-butyl-4,5,9,10-tetrahydropyrene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 4.0h， 以75%的产率得到2,7-二叔丁基芘
  参考文献：
  名称：

  Metacyclophanes and related compounds. 19. Reaction of 8-methoxy[2.2]metacyclophanes with iodine in benzene solution. A preparative route to pyrenes

  摘要：

  DOI：

  10.1021/jo00391a004
• 作为产物：
  描述：

  5,13-di-tert-butyl-8-methoxy<2.2>metacyclophane 在 benzyltrimethylammonium tribromide 作用下， 以 溶剂黄146 为溶剂， 反应 0.08h， 以96.8%的产率得到2,7-di-tert-butyl-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

• Pyrolysis of Dimethoxy[<i>n</i>.2]Metacyclophanes: An Intramolecular Condensation Reaction to Give Oxa[<i>n</i>.2.1](1,3,2)Cyclophanes
  作者：Jung-Hee Do、Yuta Yamada、Bigyan Sharma、Takehiko Yamato

  DOI：10.3184/174751912x13296759770106

  日期：2012.3

  1](1,3,2)cyclophane in 35% yield arising from intramolecular condensation reaction of syn-8,16-dimethoxy[2.2]metacyclophane; similar results were also obtained in the pyrolysis of the higher anti- and syn-dimethoxy[3.2] metacyclophane to afford the corresponding 18-oxa[3.2.1](1,3,2)cyclophane. The mechanism of this novel intramolecular condensation reaction is discussed.

  反 8,16-二甲氧基[2.2] 间环烷在 500°C 下热解得到 17-氧杂[2.2.1](1,3,2)环烷，产率 35%二甲氧基[2.2]间环芳烷；在较高的反和顺二甲氧基[3.2]元环烷的热解中也获得了类似的结果，以提供相应的18-氧杂[3.2.1](1,3,2)环烷。讨论了这种新型分子内缩合反应的机理。
• Berg, Arne; Lam, Joergen; Hansen, Poul Erik, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 8, p. 665 - 677
  作者：Berg, Arne、Lam, Joergen、Hansen, Poul Erik

  DOI：——

  日期：——
• Metacyclophanes and related compounds. 21. Nitration of [2.2]metacyclophanes
  作者：Masashi Tashiro、Shuntaro Mataka、Yoshinori Takezaki、Michinori Takeshita、Takashi Arimura、Akihiko Tsuge、Takehiko Yamato

  DOI：10.1021/jo00263a036

  日期：1989.1
• Metacyclophanes and related compounds. 14. Preparation of 8,16-difluoro[2.2]metacyclophane
  作者：Masashi Tashiro、Takehiko Yamato

  DOI：10.1021/jo00216a026

  日期：1985.8
• Sato,T.; Torizuka,K., Journal of the Chemical Society. Perkin transactions II, 1978, p. 1199 - 1204
  作者：Sato,T.、Torizuka,K.

  DOI：——

  日期：——