2-(3,5-dimethylphenyl)[1,4]benzoquinone | 358740-19-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(3,5-dimethylphenyl)[1,4]benzoquinone
• 英文别名: 2-(3,5-Dimethylphenyl)cyclohexa-2,5-diene-1,4-dione
• CAS: 358740-19-9
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: IDIOAZZKQIBMJD-UHFFFAOYSA-N

物化性质

• 熔点：
  101 °C(Solv: 1-butanol (71-36-3))
• 沸点：
  359.4±42.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间二甲苯 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-(3,5-dimethylphenyl)[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

• Mn-Catalyzed 1,6-conjugate addition/aromatization of <i>para</i>-quinone methides
  作者：Bobin Yang、Wei Yao、Xiao-Feng Xia、Dawei Wang

  DOI：10.1039/c8ob01057a

  日期：——

  A series of ferrocenyl triazole ligands have been synthesized and characterized, which proved to be effective for the Mn-catalyzed 1,6-conjugate addition/aromatization of para-quinone methides.

  一系列二茂铁三唑配体已被合成和表征，证明对锰催化的1,6-共轭加成/芳构化反应具有有效性，该反应针对对醌亚甲基。
• Optical recording medium
  申请人：Kabushiki Kaisha Toshiba

  公开号：US20030104285A1

  公开（公告）日：2003-06-05

  Disclosed is an optical recording medium comprising a recording layer. The recording layer contains: a charge generation material generating an electron and a hole by light irradiation; a charge transport material transporting one of the electron and the hole; a charge trap which traps the transported one of the electron and the hole to separate the electron and the hole; and a non-linear optical material which changes optical properties of the recording layer in accordance with electric field formed by the electron and the hole being separated from each other. The non-linear optical material has an asymmetrical carbon atom and a cyclic group. Or, it is a cyclic-group-containing constituent having: an inversion symmetric pi-electron system; at least one of an electron donating group and an electron accepting group which are bonded to the inversion symmetric &pgr;-electron system; and an asymmetrical carbon atom.

  本发明公开了一种光学记录介质，它包括一个记录层。记录层包含：通过光照射产生电子和空穴的电荷发生材料；传输电子和空穴之一的电荷传输材料；捕获传输的电子和空穴之一以分离电子和空穴的电荷阱；以及根据电子和空穴相互分离形成的电场改变记录层光学特性的非线性光学材料。非线性光学材料具有一个不对称碳原子和一个环状基团。或者，它是一种含环状基团的成分，具有：反转对称π-电子系统；至少一个与反转对称π-电子系统成键的电子供体基团和电子受体基团；以及一个不对称碳原子。
• FeSO4-promoted direct arylation of benzoquinones with ArB(OH)2 or ArBF3K
  作者：Kimihiro Komeyama、Tetsuya Kashihara、Ken Takaki

  DOI：10.1016/j.tetlet.2012.12.031

  日期：2013.2

  FeSO4 center dot 7H(2)O was proven to work as effective promoter for the direct arylation of benzoquinones with aryl boronic acids in the presence of K2S2O8. In the arylation, slow addition of iron solution was crucial to efficiently proceed with the reaction. Interestingly, the Fe-mediated arylation could be converted into a catalytic reaction by using hydroquinones, instead of benzoquinones, or addition of ascorbic acid. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.