phenyl(2-phenylquinoxalin-6-yl)methanone | 1338368-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl(2-phenylquinoxalin-6-yl)methanone
• 英文别名: Phenyl-(2-phenylquinoxalin-6-yl)methanone；phenyl-(2-phenylquinoxalin-6-yl)methanone
• CAS: 1338368-84-5
• 化学式: C₂₁H₁₄N₂O
• 分子量: 310.355
• InChiKey: UJKYMBAEEKEDNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二氨基二苯甲酮 、 2-溴苯乙酮 在 K₁₀-montmorillonite clay 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以85%的产率得到phenyl(2-phenylquinoxalin-6-yl)methanone
  参考文献：
  名称：

  One-pot synthesis of 2-substituted quinoxalines using K10-montmorillonite as heterogeneous catalyst

  摘要：

  An efficient one-pot synthesis of 2-substituted quinoxalines from 1,2-diamines and phenacyl bromides is developed using K10-montmorillonite (K10 clay) as a catalyst at 50 degrees C in acetonitrile medium. This method offers an easy route for the synthesis of substituted quinoxalines in high yields. A plausible mechanism is proposed in which quinoxalines are formed via dehydration-dehydrohalogenationcyclization sequence. Further, the K10 clay catalyst is recovered by simple filtration and reused six times without any loss in its catalytic activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.087

文献信息

• Iodine-mediated oxidative annulation for one-pot synthesis of pyrazines and quinoxalines using a multipathway coupled domino strategy
  作者：K. K. Durga Rao Viswanadham、Muktapuram Prathap Reddy、Pochampalli Sathyanarayana、Owk Ravi、Ruchir Kant、Surendar Reddy Bathula

  DOI：10.1039/c4cc05844e

  日期：——

  iodine-mediated oxidative annulation of aryl acetylenes-arylethenes-aromatic ketones with 1,2-diamines for the synthesis of pyrazines and regioselective synthesis of quinoxalines is presented. A multipathway coupled domino approach has been developed for the one-pot synthesis of 1,4-diazines with high functional group compatibility.

  提出了一种有效的碘介导的芳基乙炔-芳烃-芳族酮与1,2-二胺的氧化环合反应，用于吡嗪合成和区域选择性合成喹喔啉。已开发出一种多途径偶联多米诺骨牌方法，用于一锅法合成具有高官能团相容性的1,4-二嗪。
• Copper-catalyzed aerobic oxidative coupling of o-phenylenediamines with 2-aryl/heteroarylethylamines: direct access to construct quinoxalines
  作者：Kovuru Gopalaiah、Anupama Saini、Sankala Naga Chandrudu、Devarapalli Chenna Rao、Harsh Yadav、Binay Kumar

  DOI：10.1039/c7ob00122c

  日期：——

  A copper-catalyzed oxidative coupling reaction of o-phenylenediamines with 2-aryl/heteroarylethylamines using molecular oxygen as an oxidant has been developed. This approach provides a practical and direct access to construct quinoxalines in excellent yields at room temperature. The reaction has a broad substrate scope and exhibits excellent functional-group tolerance. This method could be easily

  已经开发出使用分子氧作为氧化剂的邻苯二胺与2-芳基/杂芳基乙胺的铜催化的氧化偶联反应。这种方法提供了一种实用且直接的途径，可以在室温下以优异的产率构建喹喔啉。该反应具有广泛的底物范围并且表现出优异的官能团耐受性。该方法可以容易地扩大规模，并应用于具有喹喔啉结构支架的生物活性分子的合成。
• Synthesis of Quinoxaline Derivatives Using TiO₂Nanoparticles as an Efficient and Recyclable Catalyst
  作者：Heshmatollah Alinezhad、Mahmood Tajbakhsh、Fatemeh Salehian、Pourya Biparva

  DOI：10.5012/bkcs.2011.32.10.3720

  日期：2011.10.20

  $TiO_2$ nanoparticles were synthesized and characterized by SEM and XRD techniques. The $TiO_2$ nanoparticles were employed as a recyclable, inexpensive and efficient catalyst for the synthesis of substituted quinoxalines in high to excellent yields and in relatively short duration.

  合成了纳米级的二氧化钛（$TiO_2$）并通过扫描电子显微镜（SEM）和X射线衍射（XRD）技术进行了表征。这些$TiO_2$纳米颗粒作为一种可回收、廉价且高效的催化剂，用于合成取代的喹啉，得到了高至优良的产率，并且用时相对较短。
• A Modified Synthesis of Some Novel Polycyclic Aromatic Phenazines and Quinoxalines by Using the Tungstate Sulfuric Acid (TSA) as a Reusable Catalyst under Solvent-free Conditions
  作者：Bahador Karami、Saeed Khodabakhshi、Marzieh Nikrooz

  DOI：10.1002/jccs.201100421

  日期：2012.2

  Considering the synthesis of new compounds, we developed heterocyclic chemistry. We also helped to improve the classical synthetic route for the synthesis of quinoxalines and phenazines through implement in terms of solvent‐free reaction. For the condensation of 1,2‐dicarbonyls and o‐phenylenediamines under solvent‐free conditions at room temperature, tungstate sulfuric acid (TSA) was found to be an

  考虑到新化合物的合成，我们开发了杂环化学。我们还通过在无溶剂反应方面的实施，帮助改进了喹喔啉和吩嗪合成的经典合成路线。对于室温下无​​溶剂条件下的1,2-二羰基和邻苯二胺的缩合反应，钨酸硫酸（TSA）是一种有效且可重复使用的试剂。纯产物的高收率和催化剂的简单制备已允许使用该方法合成几种吩嗪和喹喔啉。
• Elemental Sulfur-Mediated Synthesis of Quinoxalines from Sulfoxonium Ylides
  作者：Trayambek Nath Chaubey、Paran J. Borpatra、Satyendra Kumar Pandey

  DOI：10.1021/acs.orglett.3c01907

  日期：2023.7.21

  A novel straightforward and catalyst-free approach for synthesizing quinoxaline derivatives from sulfoxonium ylides and o-phenylenediamines mediated by elemental sulfur has been described. Due to the simple and mild reaction conditions, the sulfoxonium ylides and o-phenylenediamines decorated with different functional groups furnished moderate to high yields of quinoxaline derivatives and were well

  描述了一种由硫叶立德和邻苯二胺以元素硫介导合成喹喔啉衍生物的简单且无催化剂的新方法。由于反应条件简单温和，不同官能团修饰的亚砜叶立德和邻苯二胺提供了中等到高产率的喹喔啉衍生物，并且具有良好的耐受性。最后，使用大规模反应、吡嗪的合成和一些生物活性化合物来说明所开发方法的潜在效用。