biphenylene-1,4-diol | 406707-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: biphenylene-1,4-diol
• CAS: 406707-40-2
• 化学式: C₁₂H₈O₂
• 分子量: 184.194
• InChiKey: KTNRELOIBHMEKA-UHFFFAOYSA-N

物化性质

• 沸点：
  536.1±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  环戊二烯 、 biphenylene-1,4-diol 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 (1R,8S,9S,12R)-pentacyclo[6.4.4.19,12.01,8.02,7]heptadeca-2,4,6,10,14-pentaene-13,16-dione 、 pentacyclo[6.4.4.1^9,12.0^1,8.0^2,7]heptadeca-2,4,6,10,14-pentaene-13,16-dione
  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
• 作为产物：
  描述：

  1,4-diacetyloxybiphenylene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以72%的产率得到biphenylene-1,4-diol
  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

• POLYAZOLE FIBER AND METHOD FOR PRODUCING SAME
  申请人：Teijin Limited

  公开号：EP1947222A1

  公开（公告）日：2008-07-23

  This invention seeks to provide a fiber formed of an aromatic polyazole that has a high molecular weight and is excellent in mechanical properties such as elastic modulus, strength, etc., and a process for the production thereof. This invention provides a fiber formed of a polyazole containing a recurring unit of the following formula (1), wherein Ar1 is a divalent aromatic group having 4 to 20 carbon atoms, Ar2 is a tetravalent aromatic group having 4 to 20 carbon atoms and each X is O, S or NH, and having a phosphorus atom content of 30 ppm or less, and a process for the production thereof.

  本发明旨在提供一种由芳香族聚唑形成的纤维，该纤维具有高分子量和优异的机械性能，如弹性模量、强度等，以及其生产工艺。 本发明提供了一种由含有下式 (1) 循环单元的聚唑形成的纤维、 其中 Ar1 是具有 4 至 20 个碳原子的二价芳香基团，Ar2 是具有 4 至 20 个碳原子的四价芳香基团，每个 X 是 O、S 或 NH、 且磷原子含量不超过 30 ppm，以及其生产工艺。
• POLYAZOLE FIBER AND PROCESS FOR THE PRODUCTION THEREOF
  申请人：Chokai Masayuki

  公开号：US20100222544A1

  公开（公告）日：2010-09-02

  This invention seeks to provide a fiber formed of an aromatic polyazole that has a high molecular weight and is excellent in mechanical properties such as elastic modulus, strength, etc., and a process for the production thereof. This invention provides a fiber formed of a polyazole containing a recurring unit of the following formula (1), wherein Ar 1 is a divalent aromatic group having 4 to 20 carbon atoms, Ar 2 is a tetravalent aromatic group having 4 to 20 carbon atoms and each X is O, S or NH, and having a phosphorus atom content of 30 ppm or less, and a process for the production thereof.
• US4435294A
  申请人：——

  公开号：US4435294A

  公开（公告）日：1984-03-06
• 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.