4a-bromo-4a,8b-dihydrobiphenylene-1,4-dione | 189313-34-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4a-bromo-4a,8b-dihydrobiphenylene-1,4-dione
• 英文别名: 8b-bromo-4aH-biphenylene-1,4-dione
• CAS: 189313-34-6
• 化学式: C₁₂H₇BrO₂
• 分子量: 263.09
• InChiKey: PBRUXBFVEGSBNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4a-bromo-4a,8b-dihydrobiphenylene-1,4-dione 在 三乙胺 作用下， 以 氯仿 为溶剂， 生成 C₂₄H₁₂O₄
  参考文献：
  名称：

  A New Antiaromatic Compound:  1,4-Biphenylenequinone Synthesis and Trapping Reactions

  摘要：

  DOI：

  10.1021/jo970458s
• 作为产物：
  描述：

  4a,8b-Dihydro-biphenylene-1,4-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 4a-bromo-4a,8b-dihydrobiphenylene-1,4-dione
  参考文献：
  名称：

  A New Antiaromatic Compound:  1,4-Biphenylenequinone Synthesis and Trapping Reactions

  摘要：

  DOI：

  10.1021/jo970458s

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.
• A New Antiaromatic Compound:  1,4-Biphenylenequinone Synthesis and Trapping Reactions
  作者：Hamdullah Kiliç、Metin Balci、Ersin Yurtsever

  DOI：10.1021/jo970458s

  日期：1997.5.1