2-phenyl-3-benzoylquinoxaline 1,4-dioxide | 13494-38-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-phenyl-3-benzoylquinoxaline 1,4-dioxide
• 英文别名: 2-Benzoyl-3-phenyl-chinoxalin-1,4-dioxid；2-Benzoyl-3-phenylquinoxaline 1,4-dioxide；(1-oxido-4-oxo-3-phenylquinoxalin-4-ium-2-yl)-phenylmethanone
• CAS: 13494-38-7
• 化学式: C₂₁H₁₄N₂O₃
• 分子量: 342.354
• InChiKey: GMZCERZZUVPDQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-3-benzoylquinoxaline 1,4-dioxide 在 phosphorus tetraiodide 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以67%的产率得到2-苄基-3-苯基喹喔啉
  参考文献：
  名称：

  Demirdji, S. H.; Haddadin, M. J.; Issidorides, C. H., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1735 - 1737

  摘要：

  DOI：
• 作为产物：
  描述：

  2-<<(phenyloxy)nitros>oxy>-3-phenylquinoxaline 1,4-dioxide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以72%的产率得到2-phenyl-3-benzoylquinoxaline 1,4-dioxide
  参考文献：
  名称：

  Oxidative elimination of nitrous acid from nitrate esters. Preparation of Mecadox

  摘要：

  DOI：

  10.1021/jo00201a028

文献信息

• Quinoxaline derivatives
  申请人：Research Corporation

  公开号：US04343942A1

  公开（公告）日：1982-08-10

  The synthesis of quinoxaline and benzimidazole-N-oxides and of ester and amide derivatives of 3-hydroxy-2-quinoxalinecarboxylic acid by a novel process consisting of the reaction between a benzofuroxan and an activated methylene-containing compound under basic conditions.

  喹啉和苯并咪唑-N-氧化物的合成，以及3-羟基-2-喹啉羧酸的酯和酰胺衍生物的合成，通过一种新颖的过程实现，该过程包括在碱性条件下对苯并呋喃酰胺和含活性亚甲基的化合物进行反应。
• The reactions of benzofuroxan with carbonyl compounds on the surface of solid catalysts
  作者：Tohru Takabatake、Yumiko Hasegawa、Minoru Hasegawa

  DOI：10.1002/jhet.5570300602

  日期：1993.12

  The cyclocondensations of benzofuroxan 1a with carbonyl compounds were smoothly and efficiently carried out by the adsorption of the components on the surface of silica gel or a molecular sieve to form a 2,3-disubstituted quinoxaline 1,4-dioxide. When the reactions using a molecular sieve 3A (powder) were carried out at 90°, the actual reaction times were reduced to 0.5-2 hours. Although Duerckheimer

  通过将组分吸附在硅胶或分子筛的表面上以形成2，3-二取代的喹喔啉1，4-二氧化物，苯并呋喃喃1a与羰基化合物的环缩反应可以平稳有效地进行。当在90°下使用分子筛3A（粉末）进行反应时，实际反应时间减少到0.5-2小时。尽管Duerckheimer报告了当使5-甲氧基苯并呋喃1e与乙酰乙酸乙酯2j反应时仅分离出7-取代的喹喔啉1,4-二氧化物，但通过我们的方法，它仅生成了6-甲氧基异构体作为反应产物。5-羧基苯并呋喃聚糖1f不与羰基化合物反应。
• Reactions of Benzofuroxan with 1,3-Diketones or β-Ketoesters on Silica Gel or Alumina
  作者：Minoru Hasegawa、Tohru Takabatake

  DOI：10.1055/s-1985-31391

  日期：——

  The cyclocondensation of benzofuroxan with 1,3-diketones, 3-oxoalkanoic esters, butanedioic esters, or 3-oxoalkanamides in the presence of silica gel (adsorption of the components on silica gel) represents a convenient method for the synthesis of 2,3-disubstituted quinoxaline-1,4-bis-oxides.

  苯并呋咱氧化物与1,3-二酮、3-氧代烷酸酯、丁二酸酯或3-氧代烷酰胺在硅胶存在下的环化缩合反应（各组分吸附在硅胶上），代表了一种合成2,3-二取代喹喔啉-1,4-二氧化物的简便方法。
• Synthesis, crystal and molecular structure of 2-methyl-3-carboethoxyquinoxaline 1,4-dioxide
  作者：Shu-Kun Lin、Qiu-Zhi Cong

  DOI：10.1016/0022-2860(87)80046-7

  日期：1987.7

  Abstract 2-Methyl-3-carboethoxyquinoxaline 1,4-dioxide (MCQO) was prepared and single crystals were grown out of the reaction mixture. The structure of MCQO was established by single-crystal X-ray crystallography using a direct method. The crystals are triclinic, space group P 1 , with a = 6.928(1), b = 8.109(1), c = 10.552(1) A, α = 83.445(8), β = 85.861(10), γ = 79.168 (8)°, V = 577.7 A3, Z = 2 and

  摘要 制备了 2-Methyl-3-carboethoxyquinoxaline 1,4-dioxide (MCQO) 并从反应混合物中生长出单晶。MCQO 的结构是通过单晶 X 射线晶体学使用直接方法建立的。晶体为三斜晶系，空间群 P 1 ，a = 6.928(1), b = 8.109(1), c = 10.552(1) A, α = 83.445(8), β = 85.861(10), γ = 79.168 (8)°，V = 577.7 A3，Z = 2 和 Dc = 1.428 g cm−3。对于 1454 次反射，结构被细化为 R = 0.059。母体喹喔啉环的平面几何形状与化合物中稠合杂环系统的芳香性一致。平均NO键长为1.297(5)A，具有一定的双键特性。X 射线分析证实了此类杂芳族 N-氧化物结构的 IR、NMR 和 ESR 光谱证据。
• Silica Gel Catalyzed Synthesis of Quinoxaline 1,4-Dioxides under Solvent-Free Conditions Using Microwave Irradiation
  作者：Tohru Takabatake、Yusuke Sumiyoshi、Hiroaki Saito、Shinichi Miyairi

  DOI：10.3987/com-08-11588

  日期：——

  We report on the simple and quick synthesis of quinoxaline 1,4-dioxides in solvent-free conditions under microwave irradiation. Heating of various benzofuroxans and beta-ketoesters or 1,3-diketones adsorbed on silica gel in a microwave oven for two minutes affords diverse biologically attractive quinoxaline 1,4-dioxides in high to excellent yields. Silica gel functions not only as support using microwave but also as catalyst and dehydration reagent.