2,3-bis(4-fluorophenyl)-6-nitroquinoxaline | 350687-58-0

• 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: 2,3-bis(4-fluorophenyl)-6-nitroquinoxaline
• CAS: 350687-58-0
• 化学式: C₂₀H₁₁F₂N₃O₂
• mdl: MFCD01819591
• 分子量: 363.323
• InChiKey: YFJIFEYBYUCVNL-UHFFFAOYSA-N

物化性质

• 熔点：
  174-176 °C
• 沸点：
  479.6±40.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-bis(4-fluorophenyl)-6-nitroquinoxaline 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2,3-Bis(4-fluorophenyl)quinoxalin-6-amine
  参考文献：
  名称：

  Quinoxalinylurea derivatives as a novel class of JSP-1 inhibitors

  摘要：

  A series of quinoxalinylurea-based inhibitors are synthesized and shown to be the novel and potent inhibitors against Jnk Stimulatory Phosphatase-1 (JSP-1), which is a special member of dual-specificity protein phosphatase (DSP) family. Biological assay and computational modeling studies showed the compounds were reversible and noncompetitive inhibitors of JSP-1. JSP-1 inhibitors may be useful for the treatment of inflammatory, vascular, neurodegenerative, metabolic, and oncological diseases in humans associated with dysfunctional Jnk signaling. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.094
• 作为产物：
  描述：

  4,4'-二氟安息香 、 4-硝基邻苯二胺 在 吗啉 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以81%的产率得到2,3-bis(4-fluorophenyl)-6-nitroquinoxaline
  参考文献：
  名称：

  Yb modified NaY zeolite: A recyclable and efficient catalyst for quinoxaline synthesis

  摘要：

  DOI：

  10.1016/j.cclet.2014.03.003

文献信息

• A Green and Efficient Protocol for the Synthesis of Quinoxaline, Benzoxazole and Benzimidazole Derivatives Using Heteropolyanion-Based Ionic Liquids: As a Recyclable Solid Catalyst
  作者：Seyed Vahdat、Saeed Baghery

  DOI：10.2174/1386207311316080004

  日期：2013.8.1

  green synthesis of 2,3-disubstitutedquinoxaline derivatives. These ionic liquids are in the solid state at room temperature and the synthesis is carried out via the one-pot condensation reaction of various o-phenylenediamine with 1,2-diketone derivatives. Benzoxazole and benzimidazole derivatives were also synthesized by these novel catalysts via the one-pot condensation from reaction orthoester with

  在本文中，我们介绍了两种由丙烷磺酸盐官能化的有机阳离子和杂多阴离子组成的非常规离子液体化合物，作为绿色固体酸催化剂，可高效高效地绿色合成2,3-二取代喹喔啉衍生物。这些离子液体在室温下为固态，并且通过各种邻苯二胺与1,2-二酮衍生物的一锅缩合反应进行合成。这些新催化剂还通过原酸酯与邻氨基苯酚（苯并恶唑衍生物的合成）和邻苯二胺（苯并咪唑衍生物的合成）的一锅缩合反应合成了苯并恶唑和苯并咪唑的衍生物。所有实验均成功产生了所需的产物。
• Aqueous Hydrofluoric Acid Catalyzed Facile Synthesis of 2,3,6-Substituted Quinoxalines
  作者：A. Chandra Shekhar、A. Ravi Kumar、G. Sathaiah、K. Raju、P. V. S. S. Srinivas、P. Shanthan Rao、B. Narsaiah

  DOI：10.1002/jhet.1753

  日期：2014.9

  A versatile synthetic route for the preparation of 2,3,6‐trisubstituted quinoxalines in excellent yield is developed from θ‐diamines and 1,2‐dicarbonyl compounds in which aqueous hydrofluoric acid was employed as the medium and catalyst. Other salient features of this protocol include milder conditions, absence of coupling agents, and easy workup procedures.

  从θ-二胺和1,2-二羰基化合物（使用含水氢氟酸作为介质和催化剂）开发出了一种通用的合成路线，该路线以优异的产率制备2,3,6-三取代的喹喔啉。该协议的其他显着特征包括条件较温和，不存在偶联剂以及易于处理的程序。
• An efficient method for the synthesis of quinoxaline derivatives catalyzed by titanium silicate-1
  作者：Pranav S. Chandrachood、Amol R. Jadhav、Dinesh R. Garud、Nirmala R. Deshpande、Vedavati G. Puranik、Rajashree V. Kashalkar

  DOI：10.1007/s11164-020-04258-w

  日期：2020.12

  A series of quinoxaline derivatives were efficiently synthesized by convenient and simple procedure in excellent yields using 1 wt.% of titanium silicate (TS-1) catalyzed reaction of 1,2-diamines and 1,2-diketones in methanol at room temperature. This reaction is scalable to multigram scale and the catalyst is recyclable.

  使用 1 wt.% 的硅酸钛 (TS-1) 催化 1,2-二胺和 1,2-二酮在室温下在甲醇中的反应，通过方便和简单的程序以优异的收率高效合成了一系列喹喔啉衍生物。该反应可扩展到数克规模，并且催化剂可回收。
• Fe/Al-MCM-41: An Efficient and Reusable Catalyst for the Synthesis of Quinoxaline Derivatives
  作者：Majid. M. Heravi、Mariam Hosseini、Hossein A. Oskooie、Bita Baghernejad

  DOI：10.5012/jkcs.2011.55.2.235

  日期：2011.4.20

  Fe/Al-MCM-41을 촉매로 사용하여, 1,2-diamines과 1,2-dicarbonyl 화합물을 축합반응을 통하여 quinoxaline 계 화합물을 좋은 수율로 합성하였다. Fe/Al-MCM-41was found to be an effective catalyst for the synthesis of quinoxaline derivatives from the condensation of the 1,2-diamines and 1,2-dicarbonyl compounds in good yields. The catalyst is recyclable and reusable.

  使用Fe/Al-MCM-41作为催化剂，通过1,2-二胺和1,2-二酮化合物的缩合反应，成功合成了奎啉类化合物，产率良好。该催化剂可回收和重复使用。
• Wells-Dawson Type Heteropolyacid Catalyzed Synthesis of Quinoxaline Derivatives at Room Temperature
  作者：Majid M. Heravi、Khadijeh Bakhtiari、Fatemeh F. Bamoharram、Maryam H. Tehrani

  DOI：10.1007/s00706-007-0594-5

  日期：2007.5

  Wells-Dawson heteropolyacid (H6P2W18O62 · 24H2O) was used as an effective catalyst for the synthesis of biologically active quinoxaline derivatives from the condensation of o -phenylenediamines with 1,2-dicarbonyl compounds at room temperature in excellent yields.

  Wells-Dawson 杂多酸（H 6 P 2 W 18 O 62 ·24H 2 O）被用作从 邻 苯二胺与1,2-二羰基化合物在室温下的缩合反应合成生物活性喹喔啉衍生物的有效催化剂 。优异的产量。