1-methyl-7--(trifluoromethyl)quinoxaline-2,3(1H,4H)-dione | 61875-31-8

• 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: 1-methyl-7--(trifluoromethyl)quinoxaline-2,3(1H,4H)-dione
• 英文别名: 7-(trifluoromethyl)-1-methylquinoxalin-2,3(1H,4H)-dione；1-METHYL-7TRIFLUOROMETHYL-2(1H), 3(4H)-quinoxalinedione；4-methyl-6-(trifluoromethyl)-1H-quinoxaline-2,3-dione
• CAS: 61875-31-8
• 化学式: C₁₀H₇F₃N₂O₂
• 分子量: 244.173
• InChiKey: FPRQRWISHVFZOL-UHFFFAOYSA-N

物化性质

• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl-7--(trifluoromethyl)quinoxaline-2,3(1H,4H)-dione 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 4.42h， 生成 5-methyl-7-(trifluoromethyl)-2H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione
  参考文献：
  名称：

  1,2,4-Triazolo[4,3-a]quinoxaline-1,4-diones as antiallergic agents

  摘要：

  A series of new 1,4-dihydro-1,2,4-triazolo[4,3-]quinoxaline-1,4-diones has been prepared. These compounds were tested as inhibitors of antigen-induced release of histamine (AIR) in vitro from rat peritoneal mast cells (RMC) and as inhibitors of IgE-mediated rat passive cutaneous anaphylaxis (PCA). Most of this new class of antiallergic agents showed good activity in the RMC and PCA tests. The most potent compound, 2-acetyl-7-chloro-5-n-propyl-1,2,4-triazolo[4,3-a]quinoxaline-1,4-dione (1x), with an I50 value of 0.1 microM, is 30 times more potent than disodium cromoglycate (DSCG) in the RMC assay.

  DOI：

  10.1021/jm00381a016
• 作为产物：
  描述：

  1-Methyl-7-(trifluoromethyl)-1,2,3,4-tetrahydroquinoxalin-2-one 在 丙烷-1-硫醇 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以82%的产率得到1-methyl-7--(trifluoromethyl)quinoxaline-2,3(1H,4H)-dione
  参考文献：
  名称：

  Visible-Light-Induced Recyclable g-C3N4 Catalyzed C–H Hydroxylation of Quinoxalin-2(1H)-ones

  摘要：

  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。

  DOI：

  10.1055/a-1899-5409

文献信息

• 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。
• Quinoxaline compounds as hypnotic agents
  申请人：Eli Lilly and Company

  公开号：US03962440A1

  公开（公告）日：1976-06-08

  The present invention is concerned with the use of certain quinoxaline compounds as hypnotic agents.

  本发明涉及使用某些喹喔啉化合物作为催眠剂。
• Fluoralkyl quinoxadinediones
  申请人：Eli Lilly and Company

  公开号：US03992378A1

  公开（公告）日：1976-11-16

  The present invention is concerned with the use of certain quinoxaline compounds as hypnotic agents.

  本发明涉及使用某些喹喔啉化合物作为催眠剂。
• LOEV, B.;MUSSER, J. H.;BROWN, R. E.;JONES, H.;KAHEN, R.;HUANG, FU-CHIH;KH+, J. MED. CHEM., 1985, 28, N 3, 363-366
  作者：LOEV, B.、MUSSER, J. H.、BROWN, R. E.、JONES, H.、KAHEN, R.、HUANG, FU-CHIH、KH+

  DOI：——

  日期：——
• 1,2,4-Triazolo[4,3-a]quinoxaline-1,4-diones as antiallergic agents
  作者：Bernard Loev、John H. Musser、Richard E. Brown、Howard Jones、Robert Kahen、Fu Chih Huang、Atul Khandwala、Paula Sonnino-Goldman、Mitchell J. Leibowitz

  DOI：10.1021/jm00381a016

  日期：1985.3

  A series of new 1,4-dihydro-1,2,4-triazolo[4,3-]quinoxaline-1,4-diones has been prepared. These compounds were tested as inhibitors of antigen-induced release of histamine (AIR) in vitro from rat peritoneal mast cells (RMC) and as inhibitors of IgE-mediated rat passive cutaneous anaphylaxis (PCA). Most of this new class of antiallergic agents showed good activity in the RMC and PCA tests. The most potent compound, 2-acetyl-7-chloro-5-n-propyl-1,2,4-triazolo[4,3-a]quinoxaline-1,4-dione (1x), with an I50 value of 0.1 microM, is 30 times more potent than disodium cromoglycate (DSCG) in the RMC assay.