3-methylbenzoquinoxalin-2(1H)-one | 14279-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-methylbenzoquinoxalin-2(1H)-one
• 英文别名: 3-methyl-2-oxo-benzo(g)quinoxalinone；3-methylbenzo[g]quinoxalin-2(1H)-one；3-methyl-1H-benzo[g]quinoxalin-2-one；3-Methyl-1H-benzo[g]chinoxalin-2-on；2-Oxo-3-methyl-1,2-dihydro-6,7-benzochinoxalin；3-methyl-1H-benzo[g]quinoxalin-2-one
• CAS: 14279-60-8
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: WVSNNCAWNUZFHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  295 °C (decomp)(Solv: 1,4-dioxane (123-91-1))
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二氨基萘 、 丙酮酸 在 蔗糖 作用下， 以 水 为溶剂， 反应 72.0h， 以93%的产率得到3-methylbenzoquinoxalin-2(1H)-one
  参考文献：
  名称：

  Synthesis of potential chemotherapic quinoxalinone derivatives by biocatalysis or microwave-assisted Hinsberg reaction

  摘要：

  In recent years, great efforts have been dedicated to the design of compounds acting as selective inhibitors of the HIV-1 reverse transcriptase (RT). Due to the promissory results previously attained with some quinoxaline derivatives, we aimed to improve the specific standard Hinsberg synthetic pathway by means of biocatalysis or microwave (MW) irradiation. Both techniques rendered the products in very good yields. However, employing the microwave-assisted organic synthesis (MAOS), in the absence of solvent, the same reactions may be completed in minutes. Some of these quinoxalmone derivatives exhibited good inhibitor activity against some human tumoral cells and the lymphoma related to HIV-1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.204

文献信息

• Revisiting the Hinsberg Reaction: Facile and Expeditious Synthesis of 3-Substituted Quinoxalin-2(1H)-ones under Catalyst-Free Conditions in Water
  作者：Sabbavarapu Narayana Murthy、Bandaru Madhav、Yadavalli Venkata Durga Nageswar

  DOI：10.1002/hlca.200900358

  日期：——

  Substituted benzene‐1,2‐diamine reacted with various α‐keto esters at 50° under mild conditions for 15 min using H2O as reaction medium, providing a variety of 3‐substituted quinoxalinone derivatives in excellent yields. The reaction was instantaneous, and products were isolated by simple filtration.

  以H 2 O为反应介质，取代的1,2-二胺与各种α-酮酯在50°下于温和的条件下反应15分钟，从而以优异的收率提供了各种3-取代的喹喔啉酮衍生物。该反应是瞬时的，并且通过简单过滤分离产物。
• ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
  申请人：UNIVERSAL DISPLAY CORPORATION

  公开号：US20200350502A1

  公开（公告）日：2020-11-05

  Provided are compounds having a first ligand L A of that are useful in OLEDs as emitters.

  提供了具有第一配体LAof的化合物，可用作OLED中的发射剂。
• Kinetic study on the synthesis of some benzo[<i>g</i>]quinoxalin-2(1<i>H</i>)-one derivatives
  作者：Gabriela A. Rodrigo、Sergio G. Renou、Diana G. Bekerman、M. Inés Abasolo、Beatriz M. Fernández

  DOI：10.1002/jhet.5570340225

  日期：1997.3

  relative high values (1 × 10−1 — 1 × 10−2 min−1). On the other hand, only methanol could be used as the organic solvent for the synthesis of all of the other compounds; aqueous media always provided better results. In the 3-methyl derivative, as well as in the 3-phenyl derivative the change of the reaction pH medium modified the stoichiometry of the anelation, turning a non-quantitative reaction into a

  通过2，3-二氨基萘与几种α-二羰基化合物之间的Hinsberg反应合成了一些新颖的3-取代的苯并喹喔啉酮[R = H，CH 3，C 6 H 5，（CH 2）2 COOH]。反应的过程之后进行第二UV /可见光衍生光谱法在不同的p在25 H值（-0.89至9.0），并且还在有机溶剂°。的化合物的非取代的在C-3是唯一一个可以在良好的产率（80％）的每个介质来获得，具有相对高的值（1×10的准一级anelation速率常数-1 - 1×10 −2分钟−1）。另一方面，只有甲醇可以用作合成所有其他化合物的有机溶剂。水性介质始终提供更好的结果。在3-甲基衍生物以及在3-苯基衍生物中，反应p H介质的变化改变了芳构化的化学计量，从而将非定量反应转化为定量反应。这可以通过降低氢浓度的反应机理改变来解释，这一事实得到了互补定量hptlc实验的支持。通常，芳基化反应的拟一级反应速率常数比未取代化合物（RC
• ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE ORGANOMETALLIC COMPOUND, AND ORGANIC LIGHT-EMITTING APPARATUS INCLUDING THE ORGANIC LIGHT-EMITTING DEVICE
  申请人：Samsung Display Co., Ltd.

  公开号：US20190062357A1

  公开（公告）日：2019-02-28

  An organometallic compound is represented by Formula 1. An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and at least one of the organometallic compound. An organic light-emitting apparatus includes the organic light-emitting device.

  一种有机金属化合物由公式1表示。一种有机发光装置包括：第一电极；面向第一电极的第二电极；以及位于第一电极和第二电极之间的有机层，该有机层包括发射层和至少一种有机金属化合物。一种有机发光装置包括该有机发光装置。
• Iron-catalyzed methylation of quinoxalin-2(1H)-ones with dimethyl sulfoxide under visible light irradiation
  作者：Hong He、Zhongyi Zhang、Yicheng Zhang、Chao Zhou、Jie Liu、Lei Wang

  DOI：10.1016/j.mcat.2024.113999

  日期：2024.4

  The synthesis of iron-catalyzed -methylation of quinoxalin-2(1)-ones using dimethyl sulfoxide as the methylating reagent is described herein. The cross-coupling reactions proceeded smoothly under visible-light irradiation, which generated the corresponding products in moderate to good yields. Further investigation on the application of the methylation reaction using readily available DMSO as the methylation

  本文描述了使用二甲亚砜作为甲基化试剂的铁催化的喹喔啉-2(1)-酮的甲基化合成。交叉偶联反应在可见光照射下顺利进行，以中等至良好的收率生成了相应的产物。目前正在进一步研究使用容易获得的DMSO作为甲基化试剂的甲基化反应的应用。