2-methyl-4,5,9,10-tetrahydropyrene | 102251-75-2

• 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-methyl-4,5,9,10-tetrahydropyrene
• CAS: 102251-75-2
• 化学式: C₁₇H₁₆
• 分子量: 220.314
• InChiKey: MZYOCPPNVLMAIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C(Solv: methanol (67-56-1))
• 沸点：
  361.8±37.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 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-methyl-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83%的产率得到2-甲基芘
  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-tert-butyl-13-methyl-8-methoxy<2.2>metacyclophane 在 三氯化铝 、 硝基甲烷 、 碘 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 2-methyl-4,5,9,10-tetrahydropyrene
  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

文献信息

• A Highly Selective Transannular Route to<i>trans</i>-<i>trans</i>-1,2,3,3a,4,-5,9,10,10a,10b-Decahydropyrenes from [2.2]Metacyclophanes
  作者：Takeo Sato、Kozaburo Nishiyama、Akira Morita、Yoichi Iitaka

  DOI：10.1246/bcsj.58.2366

  日期：1985.8

  The treatment of [2.2]metacyclophanes with aluminum chloride gave a variety of hydropyrenes as the results of dehydrogenation, cycloisomerization, and disproportionation reactions. With ethylaluminum dichloride, however, a highly selective reaction occurred to give trans-trans-1,2,3,3a,4,5,9,10,10a,10b-decahydropyrene. Revised structures were presented for cis-cis- and trans-trans-decahydropyrenes

  作为脱氢、环异构化和歧化反应的结果，用氯化铝处理 [2.2] 间环芳烃会产生多种氢芘。然而，使用二氯化乙基铝时，发生了高度选择性的反应，生成反式-反式-1,2,3,3a,4,5,9,10,10a,10b-十氢芘。基于 13 C NMR 和 X 射线晶体学分析，提出了针对顺-顺-和反-反-十氢芘的修订结构。
• Yamato, Takehiko; Arimura, Takashi; Tashiro, Masashi, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1 - 8
  作者：Yamato, Takehiko、Arimura, Takashi、Tashiro, Masashi

  DOI：——

  日期：——
• 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.
• SATO, TAKEO;NISHIYAMA, KOZABURO;MORITA, AKIRA;IITAKA, YOICHI, BULL. CHEM. SOC. JAP., 1985, 58, N 8, 2366-2369
  作者：SATO, TAKEO、NISHIYAMA, KOZABURO、MORITA, AKIRA、IITAKA, YOICHI

  DOI：——

  日期：——
• YAMATO TAKEHIKO; ARIMURA TAKASHI; TASHIRO MASASHI, J. CHEM. SOC. PERKIN TRANS,(1987) N 1, 1-7
  作者：YAMATO TAKEHIKO、 ARIMURA TAKASHI、 TASHIRO MASASHI

  DOI：——

  日期：——