2-(4-ethylphenyl)quinoxaline | 1350516-03-8

• 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: 2-(4-ethylphenyl)quinoxaline
• 英文别名: 2-(4-Ethylphenyl)quinoxaline
• CAS: 1350516-03-8
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: RNSYJPCFGWXRGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  382.9±30.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 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

• 作为反应物：
  描述：

  2-(4-ethylphenyl)quinoxaline 在 copper diacetate 、 硼酸 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以90%的产率得到2-(4-ethylphenyl)-1,2,3,4-tetrahydroquinoxaline
  参考文献：
  名称：

  A quantum-chemical approach to develop tetrahydroquinoxaline as potent ferroptosis inhibitors

  摘要：

  DOI：

  10.1016/j.molstruc.2020.129485
• 作为产物：
  描述：

  4-乙基苯乙炔 在 三苯基膦氯金 、 碘苯二乙酸 、 叠氮基三甲基硅烷 、 silver trifluoromethanesulfonate 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 12.5h， 生成 2-(4-ethylphenyl)quinoxaline
  参考文献：
  名称：

  Ambient Benzotriazole Ring Opening through Intermolecular Radical Addition to Vinyltriazole

  摘要：

  Radical addition to vinyltriazole was developed as a new approach to achieve 1,2,3-triazole ring opening under mild conditions. Through reagent control, excellent chemoselectivity was achieved, giving either nitrile under basic conditions or quinoxaline under neutral conditions. Reactivities made this method an attractive new reaction mode.

  DOI：

  10.1021/acs.orglett.5b00156

文献信息

• One-Pot Construction of Indolo[2,3-<i>b</i>]quinoxalines through Ruthenium-Catalyzed <i>Ortho</i> C–H Bond Functionalization of 2-Arylquinoxalines with Sulfonyl Azides
  作者：Sudip Laru、Suvam Bhattacharjee、Sumit Ghosh、Alakananda Hajra

  DOI：10.1021/acs.orglett.1c02837

  日期：2021.10.1

  N-substituted indolo[2,3-b]quinoxalines has been developed through a Ru(II)-catalyzed ortho C–H functionalization of 2-arylquinoxalines with sulfonyl azides and further oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in one pot. This double C–N bond formation strategy provides a new efficient route for the preparation of a series of biologically relevant 6H-indolo[2,3-b]quinoxaline derivatives in

  N-取代的吲哚并[2,3- b ]喹喔啉的合成是通过Ru(II)催化的2-芳基喹喔啉与磺酰叠氮化物的邻位C-H官能化并用2,3-二氯-5进一步氧化而开发的， 6-二氰基-1,4-苯醌一锅。这种双C-N键形成策略为制备一系列生物相关的6 H-吲哚[2,3- b ]喹喔啉衍生物提供了一条新的有效途径，产率高达94%，表明底物适用范围广泛。初步的机理研究表明，连续的 C-N 键形成是通过第一步中五元钌环中间体的形成和第二步中自由基机制的形成进行的。
• Synthesis of functionalized benzimidazoles and quinoxalines catalyzed by sodium hexafluorophosphate bound Amberlite resin in aqueous medium
  作者：Pranab Ghosh、Amitava Mandal

  DOI：10.1016/j.tetlet.2012.09.045

  日期：2012.11

  for the selective synthesis of 1,2-disubstituted benzimidazoles and quinoxalines in water–methanol (1:1) mixture with the aid of resin bound hexafluorophosphate ion as catalyst is reported. The method is also effective for the incorporation of quinoxaline nucleus at the A ring of pentacyclic triterpenoid, friedelin. A plausible mechanism for the formation of disubstituted benzimidazole has also been suggested

  报道了一种非常简单，环保和通用的方法，该方法可通过树脂结合的六氟磷酸根离子作为催化剂，在水-甲醇（1：1）混合物中选择性合成1,2-二取代的苯并咪唑和喹喔啉。该方法对于在五环三萜类化合物Friedelin的A环上引入喹喔啉核也是有效的。还已经提出了形成二取代的苯并咪唑的合理机理。
• 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。
• Rh-Catalyzed tandem C–C/C–N bond formation of quinoxalines with alkynes leading to heterocyclic ammonium salts
  作者：Kangkan Talukdar、Subhasish Roy、Raghunath Bag、Tharmalingam Punniyamurthy

  DOI：10.1039/c8ob03103g

  日期：——

  An efficient Rh-catalyzed oxidative C–H activation/annulation of 2-arylquinoxalines with internal alkynes is described using Cu(OAc)2·H2O and AgBF4 to afford a diverse variety of substituted quarternary ammonium salts at room temperature. The mechanism of the protocol is established on the basis of isolation of the 5-membered rhodacycle intermediate and kinetic isotope studies. The mild reaction conditions

  使用Cu（OAc）2 ·H 2 O和AgBF 4可以在室温下用内部炔烃有效地Rh催化2-芳基喹喔啉的氧化C–H活化/环化反应，从而在室温下提供多种取代的季铵盐。该协议的机制是建立在5元Rhodacycle中间体的分离和动力学同位素研究的基础上的。温和的反应条件，底物范围和官能团多样性是突出的实用特征。
• Synthesis of libraries of quinoxalines through eco-friendly tandem oxidation–condensation or condensation reactions
  作者：Susmita Paul、Basudeb Basu

  DOI：10.1016/j.tetlet.2011.09.141

  日期：2011.12

  A facile and expeditious solid-phase synthesis of libraries of quinoxalines promoted on KF-alumina surface via tandem oxidation–condensation or condensation reactions is reported. The reaction protocol is operationally simple and mild. Moreover, solvent-free reaction condition makes the reaction procedure eco-friendly and economically viable.

  据报道，通过串联氧化-缩合或缩合反应，在KF-氧化铝表面上促进了喹喔啉库的快速简便的固相合成。该反应方案操作简单且温和。此外，无溶剂的反应条件使反应过程环保且经济可行。