2-(3-methoxyphenyl)[1,4]naphthoquinone | 94574-51-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3-methoxyphenyl)[1,4]naphthoquinone
• 英文别名: 2-(3-methoxyphenyl)naphthalene-1,4-dione
• CAS: 94574-51-3
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: LUMGPUFRACEHKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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]naphthoquinone 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]naphthoquinone
  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

• Nonaqueous arylated quinone catholytes for lithium–organic flow batteries
  作者：Dong-Seon Shin、Minjoon Park、Jaechan Ryu、Inchan Hwang、Jeong Kon Seo、Kwanyong Seo、Jaephil Cho、Sung You Hong

  DOI：10.1039/c8ta04720k

  日期：——

  synthesized in moderate to high yields by Pd-catalyzed Suzuki cross-coupling reactions. This study utilizes the synthetic quinones as redox-active organic molecules for nonaqueous lithium–organic flow batteries. The aryl moiety incorporated quinone scaffolds show enhanced electrochemical stability and rate capability. The nonaqueous catholyte, 2-phenyl-1,4-naphthoquinone, reaches a cell voltage of ∼2.6 V

  化学改性的有机氧化还原对具有可调节的氧化还原特性，高溶解度，环境友好性和成本效益的优点。受自然界的启发，通过Pd催化的Suzuki交叉偶联反应，以中等至高收率合成了一系列带有供电子甲氧基或吸电子三氟甲基的醌衍生物。这项研究利用合成的醌作为非水锂有机液流电池的氧化还原活性有机分子。结合有芳基部分的醌支架显示出增强的电化学稳定性和速率能力。非水阴极电解质2-苯基-1,4-萘醌的电池电压约为2.6 V，比容量为196 mA hg -1，而放电容量在150个循环中保持在约92％。而且，管状锂有机液流电池系统在连续循环下具有稳定的循环性能，而不会引起间歇性流量的阻塞。
• Palladium-catalyzed arylation of 1,4-naphthoquinones with aryl iodides and its synthetic application to the benzo[b]phenanthridine skeleton
  作者：Yusuke Akagi、Toshiya Komatsu

  DOI：10.1016/j.tetlet.2020.152446

  日期：2020.10

  We report a Pd-catalyzed arylation of 1,4-naphthoquinones with aryl iodides. This reaction shows excellent functional group tolerance and high regioselectivity when using nonsymmetric 1,4-naphthoquinone. Furthermore, the resulting 2-aryl-1,4-naphthoquinone could be successfully converted into benzo[b]phenanthridine-7,12-dione through treatment with aqueous ammonia, followed by oxidative cyclization

  我们报告钯与芳基碘化物催化的芳基化的芳基化。当使用非对称的1，4-萘醌时，该反应显示出优异的官能团耐受性和高的区域选择性。此外，通过用氨水处理，然后使用MnO 2进行氧化环化，可以将所得的2-芳基-1,4-萘醌成功地转化为苯并[ b ]菲啶-7,12-二酮。
• 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.
• Synthesis of aryl substituted quinones as β-secretase inhibitors: Ligand-free direct arylation of quinones with aryl halides
  作者：Dawei Wang、Bingyang Ge、Shuyan Yang、Hongyan Miao、Yuqiang Ding

  DOI：10.1134/s1070363214080295

  日期：2014.8

  The simple ligand-free direct arylation of quinones with aryl halides applying Pd(OAc)(2) as a catalyst in accordance with Heck reaction was studied. This reaction provided a simple and efficient synthetic approach to efficient inhibitors of beta-secretase aryl-substituted quinones.