6-fluoro-1-methylquinoxaline-2,3(1H,4H)-dione | 869199-11-1

• 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-fluoro-1-methylquinoxaline-2,3(1H,4H)-dione
• 英文别名: 7-fluoro-4-methyl-1H-quinoxaline-2,3-dione
• CAS: 869199-11-1
• 化学式: C₉H₇FN₂O₂
• 分子量: 194.165
• InChiKey: MCQQDTNWJPSVMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-fluoro-1-methylquinoxaline-2,3(1H,4H)-dione 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 4-(7-Fluoro-4-methyl-3-oxo-3,4-dihydro-quinoxalin-2ylamino)-N-thiophen-2-ylmethyl-benzamide
  参考文献：
  名称：

  Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors

  摘要：

  A series of 3-anilino-quinoxalinones has been identified as a new class of glycogen phosphorylase inhibitors. The lead compound I was identified through high throughput screening as well as through pharmacophore-based electronic screening. Modifications were made to the scaffold of 1 to produce novel analogues, some of which are 25 times more potent than the lead compound. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.021
• 作为产物：
  描述：

  2,5-二氟硝基苯 在 palladium on activated charcoal 氢气 、 sodium acetate 作用下， 以 乙醇 为溶剂， 80.0 ℃ 、344.74 kPa 条件下， 生成 6-fluoro-1-methylquinoxaline-2,3(1H,4H)-dione
  参考文献：
  名称：

  Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors

  摘要：

  A series of 3-anilino-quinoxalinones has been identified as a new class of glycogen phosphorylase inhibitors. The lead compound I was identified through high throughput screening as well as through pharmacophore-based electronic screening. Modifications were made to the scaffold of 1 to produce novel analogues, some of which are 25 times more potent than the lead compound. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.021

文献信息

• Quinoxalinones
  申请人：Beavers Pat Mary

  公开号：US20050148586A1

  公开（公告）日：2005-07-07

  The invention features quinoxalinones, pharmaceutical compositions containing them and methods of using them to treat, for example, diabetes.

  这项发明涉及喹喔啉酮，包含它们的药物组合物以及使用它们治疗糖尿病等疾病的方法。
• Metal‐Free C3 Hydroxylation of Quinoxalin‐2(1 <i>H</i> )‐ones in Water
  作者：Sha Peng、Die Hu、Jia‐Li Hu、Ying‐Wu Lin、Shan‐Shan Tang、Hai‐Shan Tang、Jun‐Yi He、Zhong Cao、Wei‐Min He

  DOI：10.1002/adsc.201901163

  日期：2019.12.17

  A practical protocol for the preparation of quinoxaline‐2,3(1H,4H)‐diones through direct C(sp2)−H hydroxylation of quinoxalin‐2(1H)‐ones in recyclable DL‐α‐Tocopherol methoxypolyethylene glycol succinate solution (2 wt% in water) (TPGS‐750‐M/H2O) was developed. The target products were exclusively generated and could be collected through extraction and recrystallization.

  通过可循环的DL-α-生育酚甲氧基聚乙二醇中的喹喔啉-2（1 H）-one的直接C（sp 2）-H羟基化制备喹喔啉-2-3,3 （1 H，4 H）-二酮的实用协议开发了琥珀酸盐溶液（在水中为2 wt％）（TPGS-750-M / H 2 O）。目标产物是专门产生的，可以通过萃取和重结晶来收集。
• Visible-Light-Induced Recyclable g-C3N4 Catalyzed C–H Hydroxylation of Quinoxalin-2(1H)-ones
  作者：Long-Yong Xie、Sha Peng、Qi-Xin Xie、Yi-Dan Chen、Jia-Yi Zhou

  DOI：10.1055/a-1899-5409

  日期：2023.2

  A visible-light-promoted hydroxylation of quinoxalin-2(1H)-ones using recyclable graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst has been developed. This protocol enables the selective synthesis of various hydroxyl-containing quinoxalin-2(1H)-ones in good to excellent yields under an ambient air atmosphere. Importantly, this heterogeneous catalyst can be used at least six times without significant loss of activity.

  摘要：本文报道了一种可回收的石墨烯碳氮化物（g-C3N4）作为异相光催化剂，促进喹诺啉-2（1H）-酮的可见光催化羟基化反应。该方法在常温常压空气下，能够高选择性地合成各种含羟基的喹诺啉-2（1H）-酮产物，产率良好至优良。重要的是，该异相催化剂可以重复使用至少六次而不会显著降低活性。
• Ionic liquid-catalysed regioselective oxygenation of quinoxalin-2(1<i>H</i>)-ones under visible-light conditions
  作者：Gaurav Badhani、Valvi Mangesh Biramya、Subbarayappa Adimurthy

  DOI：10.1039/d3nj04496c

  日期：——

  liquid-catalysed oxygenation of quinoxalin-2(1H)-one utilizing aerobic oxygen as a green oxidant under visible light conditions at room temperature has been described. Various N-1-alkyl and aryl-substituted quinoxalin-2(1H)-ones provided good yields of the desired products. The ionic-liquid tetramethylammonium hydroxide (TMAH) employed is readily available and promotes the oxygenation under additive

  描述了在室温可见光条件下利用有氧氧作为绿色氧化剂的离子液体催化的喹喔啉-2(1H)-酮氧化反应。各种N -1 -烷基和芳基取代的喹喔啉-2(1 H )-酮提供了良好收率的所需产物。所用的离子液体四甲基氢氧化铵（TMAH）很容易获得，并且在无添加剂和无碱条件下促进氧化。本程序说明了克级反应的适用性，并展示了目标产物随后转化为糖原磷酸化酶抑制剂。
• (3-OXO-3,4-DIHYDRO-QUINOXALIN-2-YL-AMINO)-BENZAMIDE DERIVATIVES AND RELATED COMPOUNDS AS GLYCOGEN PHOSPHORYLASE INHIBITORS FOR THE TREATMENT OF DIABETES AND OBESITY
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1711184B1

  公开（公告）日：2007-07-18