2-naphthalen-2-yl[1,4]benzoquinone | 6295-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthalen-2-yl[1,4]benzoquinone
• 英文别名: 2-(Naphthalen-2-yl)cyclohexa-2,5-diene-1,4-dione；2-naphthalen-2-ylcyclohexa-2,5-diene-1,4-dione
• CAS: 6295-48-3
• 化学式: C₁₆H₁₀O₂
• 分子量: 234.254
• InChiKey: MSCCYTHLPNDBAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 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：

  二苯基富烯 、 2-naphthalen-2-yl[1,4]benzoquinone 在 氧气 、 palladium diacetate 、 silver carbonate 、 N-乙酰甘氨酸 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 16.0h， 以32%的产率得到
  参考文献：
  名称：

  中继脱氢[2+2+2]环加成法合成聚芳基醌

  摘要：

  聚芳基醌在光电子学、光催化、生物成像和药学相关材料中有很多应用。然而，它们的合成通常具有挑战性，并且受到各种瓶颈步骤的困扰。在这里，我们展示了将富烯部分中继添加到醌上。开发的配体辅助 Pd 催化的脱氢 [2 + 2 + 2] 环加成反应能够轻松获得一类新的聚芳基醌。实现高区域选择性的关键是将两个富烯单元精确控制地添加到 Pd 催化剂赋予的醌中。该工作还确立了反应的广泛底物范围，并深入研究了脱氢偶联反应的机理。而且，单晶 X 射线衍射揭示了有趣的包装图案，表明这些材料在光电子学中的适用性。作为该反应的实际应用，筛选了各种合成的具有结构多样性的聚芳基醌的氧化还原性能，发现它们具有更好的抗氧化或化学治疗性能。

  DOI：

  10.1021/acscatal.2c00175
• 作为产物：
  描述：

  2-碘萘 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-naphthalen-2-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

• Iron-mediated direct arylation with arylboronic acids through an aryl radical transfer pathway
  作者：Jian Wang、Shan Wang、Gao Wang、Ji Zhang、Xiao-Qi Yu

  DOI：10.1039/c2cc35468c

  日期：——

  A novel iron-mediated direct C–H arylation of quinones and pyridine analogues with arylboronic acids has been developed using dichloromethane and water as solvents at ambient temperature. FeS is employed and serves as an efficient catalyst. A detailed reaction mechanism is speculated and expounded.

  一种新型铁介导的醌和吡啶类似物与芳基硼酸直接C-H芳基化反应已开发出来，使用二氯甲烷和水作为溶剂，在常温下进行。FeS被用作高效的催化剂，详细推测并阐述了反应机理。
• 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。
• PHOSPHAPHENANTHRENE COMPOUNDS AND ORGANIC LIGHT EMITTING DIODE USING THE SAME
  申请人：Chung Kwang Choon

  公开号：US20100252818A1

  公开（公告）日：2010-10-07

  The present invention relates to new phosphaphenanthrene compounds with excellent light emitting property and an organic light emitting diode (OLED) using the same.

  本发明涉及具有优异的发光性质的新型磷代菲化合物及其所使用的有机发光二极管（OLED）。
• 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.