8,16-Dimethyl<2.2>metacyclophan-1-ene | 28746-29-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 8,16-Dimethyl<2.2>metacyclophan-1-ene
• 英文别名: anti-8,16-dimethyl[2.2]metacyclophan-1-ene；15,16-Dimethyl-<2,2>-metacyclophan-1-en；8,16-Dimethyl-<2.2>-metacyclophan-1-en；15,16-Dimethyl-[2,2]-metacyclophan-1-en；(2Z)-15,16-dimethyltricyclo[9.3.1.14,8]hexadeca-1(14),2,4,6,8(16),11(15),12-heptaene
• CAS: 28746-29-4
• 化学式: C₁₈H₁₈
• 分子量: 234.341
• InChiKey: PJKDHWSODLBVNE-LUAWRHEFSA-N

物化性质

• 熔点：
  147-148 °C(Solv: methanol (67-56-1))
• 沸点：
  380.5±42.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  8,16-Dimethyl<2.2>metacyclophan-1-ene 在 palladium on activated charcoal 作用下， 生成 10b,10c-dimethylpyrene
  参考文献：
  名称：

  Aromatic molecules bearing substituents within the cavity of the .pi.-electron cloud. XX. Syntheses of [2.2]metacyclophan-1-enes. Alternate route to trans-15,16-dialkyldihydropyrenes

  摘要：

  DOI：

  10.1021/ja00715a022
• 作为产物：
  描述：

  2,6-Bis(methoxymethyl)toluol 在 盐酸 作用下， 生成 8,16-Dimethyl<2.2>metacyclophan-1-ene
  参考文献：
  名称：

  Aromatic molecules bearing substituents within the cavity of the .pi.-electron cloud. XX. Syntheses of [2.2]metacyclophan-1-enes. Alternate route to trans-15,16-dialkyldihydropyrenes

  摘要：

  DOI：

  10.1021/ja00715a022

文献信息

• FORMATION OF 10b,10c-DIHYDRO-10b,10c-DIMETHYLPYRENES IN REACTION OF 8,16-DIMETHYL[2.2]METACYCLOPHAN-1-ENES WITH PROTONIC ACIDS
  作者：Masashi Tashiro、Kazumasa Kobayashi、Takehiko Yamato

  DOI：10.1246/cl.1985.327

  日期：1985.3.5

  Reaction of 8,16-dimethyl[2.2]metacyclophan-1-enes with protonic acids such as 57% hydroiodic acid and trifluoroacetic acid afforded the corresponding 10b,10c-dihydro-10b,10c-dimethylpyrenes. Similar reaction with 47% hydrobromic acid and 36% hydrochloric acid gave surprisingly halogenated 10b,10c-dihydro-10b,10c-dimethylpyrenes.

  8,16-二甲基[2.2]偏环-1-烯与质子酸（如 57% 的氢碘酸和三氟乙酸）反应，可得到相应的 10b,10c-二氢-10b,10c-二甲基吡喃。与 47% 的氢溴酸和 36% 的盐酸进行类似的反应，可以得到令人惊讶的卤代 10b,10c-二氢-10b,10c-二甲基吡喃。
• Selective preparation. 40. A new preparative route to 8,16-dimethyl[2.2]metacyclophan-1-ene
  作者：Masashi Tashiro、Takehiko Yamato、Kazumasa Kobayashi

  DOI：10.1021/jo00198a029

  日期：1984.11
• Synthesis, Reactions, and Structural and NMR Features of [2.2]Metacyclophane Monoenes and Their Tricarbonylchromium and Cyclopentadienyliron(+) Complexes
  作者：Reginald H. Mitchell、Limin Zhang

  DOI：10.1021/jo990721k

  日期：1999.9.1

  8,16-Dimethyl-, 5,8,13,16-tetramethyl, and 4,6,8,12,14,16-hexamethyl[2,2]metacyclophanene have been synthesized from the corresponding methyl-substituted 3-thia[3.2]metacyclophane precursors via a Wittig rearrangement-Hofmann elimination procedure. Simple addition of bromine or similar electrophiles to the bridge double bond of the cyclophane monoenes did not occur; rather, the methyl-substituted dihydropyrenes were formed. However, mono- and bis-tricarbonylchromium and monocyclopentadienyliron complexes were obtained using ligand-exchange reactions. Addition of bromine to the cyclophane bridge double bond of the iron complex did occur, but unusually slowly. Surprisingly, debromination rather than dehydrobromination occurred when the dibromo addition product was treated with a variety of bases. Photoisomerization of the monoenes and nucleophilic substitution of the metal complexes was also investigated. The geometries of the monoenes and their complexes were compared to the cyclophanes and the cyclophanedienes and to the monothia- and dithiacyclophanes, by comparison of X-ray and calculated structural data and NMR spectroscopic data. Introduction of double bonds into the cyclophane bridges causes the cyclophane step to be less steep but increases distortion of the internal atoms out of the plane of the benzene rings. Making the bridges nonidentical also causes a sideways twist of the step.
• Aromatic molecules bearing substituents within the cavity of the .pi.-electron cloud. XX. Syntheses of [2.2]metacyclophan-1-enes. Alternate route to trans-15,16-dialkyldihydropyrenes
  作者：Heinz Blaschke、Chester E. Ramey、Ian Calder、Virgil Boekelheide

  DOI：10.1021/ja00715a022

  日期：1970.6