3-phenyl-6-trifluoromethylquinoxalin-2(1H)-one | 102729-51-1

• 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: 3-phenyl-6-trifluoromethylquinoxalin-2(1H)-one
• 英文别名: 6-Trifluoromethyl-3-phenyl-2(1H)-quinoxalinone；3-Phenyl-6-trifluoromethylquinoxalinyl-1H-2-one；3-Phenyl-6-(trifluoromethyl)-2-quinoxalinol；3-phenyl-6-(trifluoromethyl)-1H-quinoxalin-2-one
• CAS: 102729-51-1
• 化学式: C₁₅H₉F₃N₂O
• 分子量: 290.244
• InChiKey: SSIFLBSQFKMBCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-phenyl-6-trifluoromethylquinoxalin-2(1H)-one 在 三氯氧磷 作用下， 反应 2.0h， 以76%的产率得到2-氯-3-苯基-6-三氟甲基喹喔啉
  参考文献：
  名称：

  Loriga, Mario; Paglietti, Giuseppe, Journal of Chemical Research, Miniprint, 1986, # 1, p. 277 - 296

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-3-苯基-6-三氟甲基喹喔啉 在 sodium hydroxide 、 水 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 3-phenyl-6-trifluoromethylquinoxalin-2(1H)-one
  参考文献：
  名称：

  Quinoxaline chemistry. Part 11. 3-Phenyl-2 [phenoxy- and phenoxymethyl]-6(7) or 6,8-substituted quinoxalines and N-[4-(6(7)-substituted or 6,8-disubstituted-3-phenylquinoxalin-2-yl)hydroxy or hydroxymethyl]benzoylglutamates. Synthesis and evaluation of in vitro anticancer activity and enzymatic inhibitory activity against dihydrofolate reductase and thymidylate synthase

  摘要：

  Twenty-four out of twenty-nine quinoxalines were selected at the National Cancer Institute, Bethesda, Md, USA, for in vitro anticancer screening. Among these, 10 derivatives exhibited high values of percent tumor growth inhibition at a concentration of 10(-4) M in all cancer cell lines. Four of these compounds maintained these values at 10(-5) M, whereas a certain number exhibited significant values of percent inhibition at the most diluted concentrations (10(-8)-10(-6) M). Inhibitory activity against dihydrofolate reductase (DHFR) (bovine and rat liver) was determined for the most active compounds. This test showed that this type of quinoxaline exhibited an appreciable activity in comparison with the previously described aza analogues. In the other test (Lactobacillus casei, thymidylate synthase (TS), human HTS) no or poor activity was detected in both series of compounds. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00054-8

文献信息

• Combining enzyme and photoredox catalysis for the synthesis of quinazolines
  作者：Wenli Li、Jiangnan Yang、Haibo Zhu、Yanxia Shen、Zhanggao Le、Zongbo Xie

  DOI：10.1016/j.mcat.2023.113549

  日期：2023.11

  an enzyme and visible-light catalysis for the synthesis of quinazoline derivatives from 2-aminobenzylamine and methyl benzoylformate is described for the first time. The reaction comprises enzyme-catalyzed hydrolysis, visible-light-activated decarboxylation, and oxidation cyclization. A series of reactions between 2-aminobenzylamine and different methyl benzoylformates afforded the corresponding products

  在此，首次描述了一种结合酶和可见光催化的新型一锅法策略，用于从 2-氨基苄胺和苯甲酰甲酸甲酯合成喹唑啉衍生物。该反应包括酶催化水解、可见光激活脱羧和氧化环化。2-氨基苄胺和不同的苯甲酰甲酸甲酯之间的一系列反应得到了相应的产物。该策略成功应用于2-氨基苯甲酰胺和邻苯二胺与苯甲酰甲酸甲酯的反应。该方法不需要额外的添加剂或过渡金属，为喹唑啉类化合物的合成提供了一种高效、环保的方法。
• 10.1021/acs.orglett.4c01624
  作者：Nguyen, Le Anh、Tran, Thi Yen、Ngo, Quoc Anh、Mac, Dinh Hung、Retailleau, Pascal、Nguyen, Thanh Binh

  DOI：10.1021/acs.orglett.4c01624

  日期：——

  We disclose the synthesis of 3-arylquinoxalin-2-ones from o-phenylenediamines and readily available arylacetates. The method harnesses the selective oxidative property of elemental sulfur in the presence of amine base catalyst and DMSO. The reactions are operationally simple and tolerate a wide range of functional groups.

  我们公开了从邻苯二胺和容易获得的芳基乙酸酯合成3-芳基喹喔啉-2-酮。该方法在胺碱催化剂和 DMSO 存在下利用元素硫的选择性氧化特性。该反应操作简单并且耐受多种官能团。
• Loriga; Piras; Sanna, Il Farmaco, 1997, vol. 52, # 3, p. 157 - 166
  作者：Loriga、Piras、Sanna、Paglietti

  DOI：——

  日期：——
• LORIGA, M.;PAGLIETTI, G., J. CHEM. RES. SYNOP., 1986, N 1, 16-17
  作者：LORIGA, M.、PAGLIETTI, G.

  DOI：——

  日期：——
• Quinoxaline chemistry. Part 11. 3-Phenyl-2 [phenoxy- and phenoxymethyl]-6(7) or 6,8-substituted quinoxalines and N-[4-(6(7)-substituted or 6,8-disubstituted-3-phenylquinoxalin-2-yl)hydroxy or hydroxymethyl]benzoylglutamates. Synthesis and evaluation of in vitro anticancer activity and enzymatic inhibitory activity against dihydrofolate reductase and thymidylate synthase
  作者：Paola Corona、Gabriella Vitale、Mario Loriga、Giuseppe Paglietti、Maria Paola Costi

  DOI：10.1016/s0014-827x(98)00054-8

  日期：1998.7

  Twenty-four out of twenty-nine quinoxalines were selected at the National Cancer Institute, Bethesda, Md, USA, for in vitro anticancer screening. Among these, 10 derivatives exhibited high values of percent tumor growth inhibition at a concentration of 10(-4) M in all cancer cell lines. Four of these compounds maintained these values at 10(-5) M, whereas a certain number exhibited significant values of percent inhibition at the most diluted concentrations (10(-8)-10(-6) M). Inhibitory activity against dihydrofolate reductase (DHFR) (bovine and rat liver) was determined for the most active compounds. This test showed that this type of quinoxaline exhibited an appreciable activity in comparison with the previously described aza analogues. In the other test (Lactobacillus casei, thymidylate synthase (TS), human HTS) no or poor activity was detected in both series of compounds. (C) 1998 Elsevier Science S.A. All rights reserved.