2-biphenyl-4-yl[1,4]benzoquinone | 3540-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-biphenyl-4-yl[1,4]benzoquinone
• 英文别名: Biphenyl-p-benzoquinone；2-(4-phenylphenyl)cyclohexa-2,5-diene-1,4-dione
• CAS: 3540-98-5
• 化学式: C₁₈H₁₂O₂
• 分子量: 260.292
• InChiKey: BXIBCAKDSIOWAN-UHFFFAOYSA-N

物化性质

• 熔点：
  199 °C
• 沸点：
  442.5±45.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-biphenyl-4-yl[1,4]benzoquinone 、 乙酸酐 在 锌 作用下， 以87%的产率得到p-Terphenyldiyl-(2.5)-diacetat
  参考文献：
  名称：

  Roetz, U.; Lindau, J.; Fischer, H., Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1993, vol. 225, p. 167 - 174

  摘要：

  DOI：
• 作为产物：
  描述：

  联苯 在 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 2-biphenyl-4-yl[1,4]benzoquinone
  参考文献：
  名称：

  Transition Metal-Free Direct C–H Functionalization of Quinones and Naphthoquinones with Diaryliodonium Salts: Synthesis of Aryl Naphthoquinones as β-Secretase Inhibitors

  摘要：

  A novel ligand-free, transition metal-free direct C-H functionalization of quinones with diaryliodonium salts has been developed for the first time. The transformation was promoted only through the use of a base and gave aryl quinone derivatives in moderate to good yields. This methodology provided an effective and easy way to synthesize β-secretase inhibitors. The radical trapping experiments showed that this progress was the radical mechanism.

  DOI：

  10.1021/jo501467v

文献信息

• Generation of Arylated Quinones by Iron-Catalyzed Oxidative Arylation of Phenols: Formal Synthesis of Phellodonin, Sarcodonin ε, Leucomelone and Betulinan A
  作者：Arghya Deb、Soumitra Agasti、Tapish Saboo、Debabrata Maiti

  DOI：10.1002/adsc.201301084

  日期：2014.3.10

  Biologically and pharmaceutically relevant arylated quinones (Quin‐Ar) have been synthesized via direct CH arylation of a variety of phenols using arylboronic acids. An inexpensive, environmentally friendly iron catalyst, ferric sulphate, Fe2(SO4)3, was employed in this operationally simple and efficient method.

  生物学和药物相关芳基化醌（奎恩基-Ar）已经合成经由直接Ç  H的各种使用芳基硼酸的酚芳基化。在这种操作简单而有效的方法中采用了一种廉价，环保的铁催化剂，硫酸铁，Fe 2（SO 4）3。
• [EN] NEUROPROTECTIVE BENZO[1,3]OXATHOL-2-ONES<br/>[FR] BENZO[1,3]OXATHIOL-2-ONES NEUROPROTECTRICES
  申请人：AEGERA THERAPEUTICS INC

  公开号：WO2005012281A1

  公开（公告）日：2005-02-10

  This invention relates to benzo[1,3]oxathiol-2-ones, derivatives, and precursors thereof, and their use as neuroprotective agents in the treatment and prevention of neuronal disorders of the central and peripheral nervous systems.

  这项发明涉及苯并[1,3]噁硫醚-2-酮及其衍生物和前体，以及它们作为神经保护剂在治疗和预防中枢和外周神经系统的神经元疾病中的应用。
• DE566521
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of Aryl- and Alkylquinones through Rhodium-Catalyzed C–C ­Coupling under Mild Conditions
  作者：Dawei Wang、Yuqiang Ding、Bingyang Ge、Liyong Du、Hongyan Miao

  DOI：10.1055/s-0034-1379472

  日期：——

  A direct arylation, alkylation of quinones with aryl and alkyl boronic acids through rhodium-catalyzed C-C coupling has been developed under mild conditions. [Cp*RhCl2](2) was shown to be the most effective catalyst for the transformation. More importantly, good to excellent yields were obtained under room temperature and base-free conditions. This reaction provides a practical, efficient method for the synthesis of aryl- and alkylquinones.
• Ir-catalyzed arylation, alkylation of quinones with boronic acids through C–C coupling
  作者：Dawei Wang、Bingyang Ge、Anqi Ju、Yucheng Zhou、Chongying Xu、Yuqiang Ding

  DOI：10.1016/j.jorganchem.2014.12.036

  日期：2015.3

  Ir-catalyzed arylation, alkylation of quinones with boronic acids was developed under room temperature. Both aryl and alkyl boronic acids are suitable for this transformation. This expands the application scope of the iridium catalyst. This is also an excellent proof that iridium catalysts can be used in the C-C coupling of quinones and naphthoquinones with alkyl boronic acids. (C) 2015 Elsevier B. V. All rights reserved.