6-methyl-2-p-tolylquinoxaline | 139436-60-5

• 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: 6-methyl-2-p-tolylquinoxaline
• 英文别名: 6-Methyl-2-(4-methylphenyl)quinoxaline
• CAS: 139436-60-5
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: GDCOYACAFFJINK-UHFFFAOYSA-N

物化性质

• 沸点：
  389.1±37.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

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：

  对甲基苯甲酰氯 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 乙醚 、 1,2-二氯乙烷 、 乙腈 为溶剂， 20.0~110.0 ℃ 、689.49 kPa 条件下， 反应 0.42h， 生成 7-methyl-2-(p-tolyl)quinoxaline 、 6-methyl-2-p-tolylquinoxaline
  参考文献：
  名称：

  Safe and Reliable Synthesis of Diazoketones and Quinoxalines in a Continuous Flow Reactor

  摘要：

  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.

  DOI：

  10.1021/ol1027927

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] 。
• RECYCLABLE ACIDIC BR0NSTED IONIC LIQUID CATALYZED SYNTHESIS OF QUINOXALINE
  作者：D TEJESWARARAO

  DOI：10.4067/s0717-97072016000100018

  日期：——

  The acidic ionic liquid, 1-(4-sulfonic acid) butyl-3-methylimidazolium hydrogen sulfate [MimC 4 SO 4 H]HSO 4 catalyzed two-component condensation reaction of phenacyl bromide and o -phenylenediamine to afford corresponding quinoxaline derivatives. The inexpensive and non-toxic ionic liquids can be reused several times without any perceptible loss of their activities.

  酸性离子液体1-（4-磺酸）丁基-3-甲基咪唑硫酸氢盐[MimC 4 SO 4 H] HSO 4催化苯甲酰溴和邻苯二胺的两组分缩合反应，得到相应的喹喔啉衍生物。廉价且无毒的离子液体可以重复使用数次，而不会损失任何活性。
• Synthesis of Quinoxaline Using Silica Supported Phosphomolybdic Acid as Reusable Heterogeneous Catalyst
  作者：D. Tejeswararao

  DOI：10.14233/ajchem.2016.19533

  日期：——

  Using phosphomolybdic acid on silica as recyclable catalyst we have developed methodology for the synthesis of quinoxalines by condensation of phenacyl bromides and o-phenylene diamines in ClCH2CH2Cl at 80 °C. The phosphomolybdic acid-silica catalyst can be reused for three successive runs with slight decrease in yield.

  我们开发了在二氧化硅上使用磷钼酸作为可回收催化剂，在 80 °C 下通过在 ClCH2CH2Cl 中缩合苯溴化物和邻苯基二胺来合成喹喔啉的方法。磷钼酸-二氧化硅催化剂可连续重复使用三次，但产率略有下降。
• 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。