tetrahydrobiphenylene | 37150-32-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: tetrahydrobiphenylene
• 英文别名: 1,2,4a,8b-Tetrahydrobiphenylene；1,2,4a,8b-tetrahydrobiphenylene
• CAS: 37150-32-6
• 化学式: C₁₂H₁₂
• 分子量: 156.227
• InChiKey: KNFWDNOIQXYAEC-UHFFFAOYSA-N

物化性质

• 沸点：
  238.5±30.0 °C(predicted)
• 密度：
  1.069±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  联苯烯 在 氢化钾 作用下， 以 四氢呋喃 为溶剂， 生成 tetrahydrobiphenylene 、 4a,8b-dihydrobiphenylene
  参考文献：
  名称：

  A new antiaromatic compound: 1,4-biphenylenequinone synthesis and trapping reactions: can a quinone unit stabilize the cyclobutadiene?

  摘要：

  The photooxygenation of 4a,8b-dihydrobiphenylene affords an endoperoxide. NEt3-catalyzed rearrangement of this endoperoxide gave the corresponding hydroxy enone, while the CoTPP-catalyzed rearrangement afforded a bisepoxide. MnO2 oxidation of hydroxy enol leads to 4a,8b-dihydrobiphenylene-1,4-dione. The NIBS bromination of this dione produces mono- and dibromides. NEt3-supported elimination of monobromide and zinc elimination of dibromide afforded the target compound, 1,4-biphenylenequinone, which was trapped as the dimer and cycloadducts with cyclopentadiene and anthracene, respectively. Furthermore, 1,4-biphenylenequinone was generated upon oxidation of biphenylene-1,4-diol with bis(trifluoroacetoxy)iodobenzene (PIFA). The stability and reactivity of the title compound is discussed. (C) 2001 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4020(01)01008-0

文献信息

• A new antiaromatic compound: 1,4-biphenylenequinone synthesis and trapping reactions: can a quinone unit stabilize the cyclobutadiene?
  作者：Hamdullah Kiliç、Metin Balci

  DOI：10.1016/s0040-4020(01)01008-0

  日期：2001.12

  The photooxygenation of 4a,8b-dihydrobiphenylene affords an endoperoxide. NEt3-catalyzed rearrangement of this endoperoxide gave the corresponding hydroxy enone, while the CoTPP-catalyzed rearrangement afforded a bisepoxide. MnO2 oxidation of hydroxy enol leads to 4a,8b-dihydrobiphenylene-1,4-dione. The NIBS bromination of this dione produces mono- and dibromides. NEt3-supported elimination of monobromide and zinc elimination of dibromide afforded the target compound, 1,4-biphenylenequinone, which was trapped as the dimer and cycloadducts with cyclopentadiene and anthracene, respectively. Furthermore, 1,4-biphenylenequinone was generated upon oxidation of biphenylene-1,4-diol with bis(trifluoroacetoxy)iodobenzene (PIFA). The stability and reactivity of the title compound is discussed. (C) 2001 Elsevier Science Ltd. Ail rights reserved.