7-methyl-2-(p-tolyl)quinoxaline | 1023743-68-1

• 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: 7-methyl-2-(p-tolyl)quinoxaline
• 英文别名: 7-Methyl-2-(4-methylphenyl)quinoxaline；7-methyl-2-(4-methylphenyl)quinoxaline
• CAS: 1023743-68-1
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: ZCJXQWOEZVQTKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,4-二氨基甲苯 、 (Z)-2-偶氮基-1-(4-甲基苯基)乙烯醇 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以94%的产率得到7-methyl-2-(p-tolyl)quinoxaline
  参考文献：
  名称：

  Cu(OTf)2-催化从α-重氮酮和芳基1,2-二胺合成喹喔啉的第一个例子

  摘要：

  α-重氮酮在 10 mol% 三氟甲磺酸铜 (II) 存在下与芳基 1,2-二胺进行平滑偶联，以优异的收率提供相应的 2-烷基-或 2-芳基-喹喔啉...

  DOI：

  10.1246/cl.2008.348

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。
• Synthesis of polycyclic 3,3′-spirooxindoles and some new 2-arylquinoxalines from (E/Z)- 1-(2-oxo-2-arylethylidene)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ones
  作者：Bahman Ebrahimi Saatluo、Ruhollah Amanollahi、Hadi Zare Fazlelahi、Mehdi M. Baradarani、John A. Joule

  DOI：10.1016/j.molstruc.2022.132445

  日期：2022.5

  A facile protocol to access a novel series of spirocyclodiazepines from cyclocondensation of 1-(2-oxo-2-arylethylidene)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ones (derived from 5,6-dihydro-1H-pyrrolo[3,2,1-ij]quinolone-1,2(4H)‑dione) with ethane-1,2-diamines and benzene-1,2-diamines, generates polycyclic spirooxindoles and unexpectedly produces 2-arylquinoxalines instead of spiro[indole-1

  从 1-(2-oxo-2-arylethyleneidene)-5,6-dihydro-4 H -pyrrolo[3,2,1- ij ]quinolin-2(1 H的环缩合获得一系列新型螺环二氮杂卓的简便方案)-ones（衍生自 5,6-dihydro-1 H - pyrrolo[3,2,1- ij ]quinolone-1,2(4 H )-dione）与 ethane-1,2-diamines 和 benzo-1，在绿色溶剂中作为有效催化剂的p- TSA存在下，2-二胺生成多环螺氧吲哚并出人意料地分别生成 2-芳基喹喔啉而不是螺[吲哚-1,5-苯二氮卓] 。
• A catalyst free, one pot approach for the synthesis of quinoxaline derivatives via oxidative cyclisation of 1,2-diamines and phenacyl bromides
  作者：Kapil Kumar、Sagar Ravso Mudshinge、Sandeep Goyal、Mukesh Gangar、Vipin A. Nair

  DOI：10.1016/j.tetlet.2015.01.138

  日期：2015.3

  A simple, efficient and eco-friendly method has been developed for quinoxaline synthesis from inexpensive and readily available diamines and phenacyl bromides by catalyst- and additive-free protocol.

  已经开发了一种简单，有效且环保的方法，通过无催化剂和无添加剂的方案，由廉价且易于获得的二胺和苯甲酰溴合成喹喔啉。
• A mild and convenient synthesis of quinoxalines via cyclization–oxidation process using DABCO as catalyst
  作者：H.M. Meshram、G. Santosh Kumar、P. Ramesh、B. Chennakesava Reddy

  DOI：10.1016/j.tetlet.2010.01.107

  日期：2010.5

  An efficient and general method has been described for the synthesis of quinoxalines by the reaction of 1,2-diamines with phenacyl bromides in the presence of DABCO. The method is suitable for the preparation of functionalized quinoxalines. (C) 2010 Elsevier Ltd. All rights reserved.
• Safe and Reliable Synthesis of Diazoketones and Quinoxalines in a Continuous Flow Reactor
  作者：Laetitia J. Martin、Andreas L. Marzinzik、Steven V. Ley、Ian R. Baxendale

  DOI：10.1021/ol1027927

  日期：2011.1.21

  A flow method for the synthesis of aliphatic and aromatic diazoketones from acyl chloride precursors has been developed and used to prepare quinoxalines in a multistep sequence without isolation of the potentially explosive diazoketone. The protocol showcases an efficient in-line purification using supported scavengers with time-saving and safety benefits and in particular a reduction in the operator's exposure to carcinogenic phenylenediamines.