2-(3-methoxyphenyl)[1,4]benzoquinone | 51134-73-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-methoxyphenyl)[1,4]benzoquinone
• 英文别名: 2-(3-Methoxyphenyl)cyclohexa-2,5-diene-1,4-dione
• CAS: 51134-73-7
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: YHKAYAODLJOKKM-UHFFFAOYSA-N

物化性质

• 熔点：
  112 °C
• 沸点：
  380.3±41.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenyl)[1,4]benzoquinone 生成 2-(3-Hydroxy-phenyl)-naphtho-1,4-chinon
  参考文献：
  名称：

  对苯二酚II通过对苯二酚的重排形成二苯并呋喃衍生物

  摘要：

  几个二醌（I，III，V）经历光化学和/或热重排，生成二苯并呋喃醌（II，IV，VI）。通过合成已经建立了结构IV，并且已经将明确的结构分配给了它的几种异构体。

  DOI：

  10.1016/0040-4020(63)85007-3
• 作为产物：
  描述：

  苯甲醚 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-methoxyphenyl)[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。
• VOLUCRISPORIN: ISOLATION, STRUCTURE, AND SYNTHESIS OF THE METHYL ETHER
  作者：P. V. Divekar、G. Read、L. C. Vining、R. H. Haskins

  DOI：10.1139/v59-289

  日期：1959.12.1

  A new pigment, volucrisporin, has been isolated from shaken cultures of the Hyphomycete Volucrisporaaurantiaca Haskins, and characterized as 2,5-(m-hydroxyphenyl)-1,4-benzoquinone. The structure has been confirmed by synthesis of the dimethyl ether.

  一种新的色素volucrisporin已从摇动培养的Hyphomycete Volucrisporaaurantiaca Haskins中分离出来，并被鉴定为2,5-(m-羟基苯基)-1,4-苯醌。该结构已通过二甲醚的合成得到确认。
• 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.