2,7-dimethyl-3-phenylquinoxaline | 68674-62-4

• 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: 2,7-dimethyl-3-phenylquinoxaline
• 英文别名: 3,6-dimethyl-2-phenylquinoxaline；3,6-dimethyl-2-phenyl-quinoxaline；3,6-Dimethyl-2-phenyl-chinoxalin；2,7-Dimethyl-3-phenyl-chinoxalin
• CAS: 68674-62-4
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: KREJAMNRPGVTSX-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-Azido-3,5-dimethyl-2-phenyl-indolenin 生成 2,7-dimethyl-3-phenylquinoxaline
  参考文献：
  名称：

  TAMURA Y.; CHUN M. W.; NISHIDA H.; KWON S.; IKEDA M., CHEM. AND PHARM. BULL., 1978, 26, NO 9, 2866-2873

  摘要：

  DOI：

文献信息

• A Green Synthesis of Quinoxalines and 2,3-Dihydropyrazines
  作者：Gabriele Micheletti、Camilla Delpivo、Carla Boga

  DOI：10.1055/s-0033-1338441

  日期：——

  Abstract Quinoxaline and dihydropyrazine derivatives were obtained in high yields by simple addition of 1,2-diamines and 1,2-dicarbonyl compounds in water. In some cases, the products spontaneously precipitated from the reaction mixture, making it possible to recover and reuse the mother liquor for further condensations. The very mild reaction conditions, the high yields of the products, and the absence

  摘要 通过在水中简单地添加1,2-二胺和1,2-二羰基化合物，可以高收率获得喹喔啉和二氢吡嗪衍生物。在某些情况下，产物自发地从反应混合物中沉淀出来，使得有可能回收并再利用母液用于进一步的冷凝。非常温和的反应条件，高收率的产品以及不存在任何催化剂，使得该方法成为生产喹喔啉和二氢吡嗪的有效而绿色的途径。 通过在水中简单地添加1,2-二胺和1,2-二羰基化合物，可以高收率获得喹喔啉和二氢吡嗪衍生物。在某些情况下，产物自发地从反应混合物中沉淀出来，使得有可能回收并再利用母液用于进一步的冷凝。非常温和的反应条件，高收率的产品以及不存在任何催化剂，使得该方法成为生产喹喔啉和二氢吡嗪的有效而绿色的途径。
• Graphene oxide (GO) or reduced graphene oxide (rGO): efficient catalysts for one-pot metal-free synthesis of quinoxalines from 2-nitroaniline
  作者：Babli Roy、Sujit Ghosh、Pranab Ghosh、Basudeb Basu

  DOI：10.1016/j.tetlet.2015.10.065

  日期：2015.12

  A straightforward one-pot preparation of library of quinoxalines from 2-nitroanilines under entirely metal-free conditions is described. Initial reduction of nitroaniline with hydrazine hydrate is efficiently catalyzed by graphene oxide (GO) or reduced graphene oxide (rGO), and further one-pot tandem reactions with 1,2-dicarbonyl compounds or with alpha-hydroxy ketones afford quinoxalines in excellent yields. The catalyst is recovered, characterized, and found to be recyclable for consecutive four runs examined with appreciable conversions. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of quinoxalines by cyclization of α-arylimino oximes of α-dicarbonyl compounds
  作者：N.P Xekoukoulotakis、C.P Hadjiantoniou-Maroulis、A.J Maroulis

  DOI：10.1016/s0040-4039(00)01847-5

  日期：2000.12

  Heating the title compounds 1 at reflux in acetic anhydride yields quinoxalines 3 and 4 via a presumed aryliminoiminyl radical 5, resulting from homolytic cleavage of the N-O bond in the intermediate ester 2. The observed regioselectivity of the reaction is also rationalized by implicating such a radical. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Kidwai, Mazaahir; Mishra, Neeraj Kumar; Bhatnagar, Divya, Asian Journal of Chemistry, 2011, vol. 23, # 11, p. 5051 - 5054
  作者：Kidwai, Mazaahir、Mishra, Neeraj Kumar、Bhatnagar, Divya、Jahan, Anwar

  DOI：——

  日期：——
• Chemoselective synthesis of quinoxalines and benzimidazoles by silica gel catalysis
  作者：Chunmei Li、Furen Zhang、Zhen Yang、Chenze Qi

  DOI：10.1016/j.tetlet.2014.08.022

  日期：2014.10

  Treatment of nitroolefins and o-phenylenediamine with silica gel catalyst produced quinoxalines mainly in THF, but gave benzimidazoles efficiently in water. Such a solvent-dependent chemoselective reaction has prominent features of affording two cyclized products selectively with the same substrate, short reaction time, operational simplicity, as well as available starting materials and nontoxic catalysts. In addition, the scope and limitations were explored and a plausible reaction mechanism is proposed. (C) 2014 Elsevier Ltd. All rights reserved.