6-chloro-2-(p-tolyl)quinoxaline | 139436-64-9

• 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-chloro-2-(p-tolyl)quinoxaline
• 英文别名: 6-Chloro-2-(4-methylphenyl)quinoxaline
• CAS: 139436-64-9
• 化学式: C₁₅H₁₁ClN₂
• 分子量: 254.719
• InChiKey: FLJDXSYKEAFLJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  4-叔丁基苯硼酸 、 6-chloro-2-(p-tolyl)quinoxaline 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以78%的产率得到6-(4-tert-butylphenyl)-2-(p-tolyl)quinoxaline
  参考文献：
  名称：

  Regioselective Suzuki-Miyaura Cross-Coupling Reactions of 2,6-Dichloroquinoxaline

  摘要：

  A variety of mono- and diarylated quinoxaline derivatives were prepared by site-selective Suzuki-Miyaura cross-coupling reactions of 2,6-dichloroquinoxaline. The selectivity is controlled by electronic parameters.

  DOI：

  10.1055/s-0031-1289754
• 作为产物：
  描述：

  2,6-二氯喹喔啉 、 4-甲苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以75%的产率得到6-chloro-2-(p-tolyl)quinoxaline
  参考文献：
  名称：

  Regioselective Suzuki-Miyaura Cross-Coupling Reactions of 2,6-Dichloroquinoxaline

  摘要：

  A variety of mono- and diarylated quinoxaline derivatives were prepared by site-selective Suzuki-Miyaura cross-coupling reactions of 2,6-dichloroquinoxaline. The selectivity is controlled by electronic parameters.

  DOI：

  10.1055/s-0031-1289754

文献信息

• 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。
• 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.
• Rao, M Hanmantha; Reddy, A Pandu Ranga; Veeranagaiah, V, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 2, p. 88 - 91
  作者：Rao, M Hanmantha、Reddy, A Pandu Ranga、Veeranagaiah, V

  DOI：——

  日期：——
• Regioselective Suzuki-Miyaura Cross-Coupling Reactions of 2,6-Dichloroquinoxaline
  作者：Peter Langer、Iftikhar Ali、Baraa Siyo、Yaseen Al-Soud、Alexander Villinger

  DOI：10.1055/s-0031-1289754

  日期：2012.6

  A variety of mono- and diarylated quinoxaline derivatives were prepared by site-selective Suzuki-Miyaura cross-coupling reactions of 2,6-dichloroquinoxaline. The selectivity is controlled by electronic parameters.