ethyl 4-ethyl-3-oxo-3,4-dihydroquinoxaline-2-carboxylate | 110450-98-1

• 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: ethyl 4-ethyl-3-oxo-3,4-dihydroquinoxaline-2-carboxylate
• 英文别名: Ethyl 4-ethyl-3-oxo-quinoxaline-2-carboxylate；ethyl 4-ethyl-3-oxoquinoxaline-2-carboxylate
• CAS: 110450-98-1
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: OQXPZNJRVQZVNS-UHFFFAOYSA-N

物化性质

• 沸点：
  375.8±25.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-ethyl-3-oxo-3,4-dihydroquinoxaline-2-carboxylate 在 sodium hydroxide 、 水 作用下， 反应 1.0h， 以68%的产率得到4-Ethyl-3,4-dihydro-3-oxo-chinoxalin-carbonsaeure-(2)
  参考文献：
  名称：

  Synthesis of substituted 2-ethoxycarbonyl- and 2-carboxyquinoxalin-3-ones for evaluation of antimicrobial and anticancer activity

  摘要：

  A series of variously substituted quinoxalin-3-ones bearing an ethoxycarbonyl or carboxy group in the C-2 position has been prepared and their structures proved by H-1 NMR spectroscopy. The obtained compounds were investigated in vitro for antimicrobial and anticancer activities. Preliminary results showed a moderate activity against a few strains of bacteria but no significant anticancer and anti-HIV activity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00044-5
• 作为产物：
  描述：

  二氧代琥珀酸二乙酯 在 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 10.0h， 生成 ethyl 4-ethyl-3-oxo-3,4-dihydroquinoxaline-2-carboxylate
  参考文献：
  名称：

  Synthesis of substituted 2-ethoxycarbonyl- and 2-carboxyquinoxalin-3-ones for evaluation of antimicrobial and anticancer activity

  摘要：

  A series of variously substituted quinoxalin-3-ones bearing an ethoxycarbonyl or carboxy group in the C-2 position has been prepared and their structures proved by H-1 NMR spectroscopy. The obtained compounds were investigated in vitro for antimicrobial and anticancer activities. Preliminary results showed a moderate activity against a few strains of bacteria but no significant anticancer and anti-HIV activity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00044-5

文献信息

• Hydrolysis products of flavins (isoalloxazines)
  作者：Takashi Harayama、Yasuhiro Tezuka、Tooru Taga、Fumio Yoneda

  DOI：10.1016/0040-4039(84)80054-4

  日期：——

  Hydrolysis of flavin (I) with Triton B gave the 4a-spirohydantoin (II) as the main product along with III, showing that a main nucleophilic attack of hydroxide ion was initiated on the 10a position of I.

  黄酮（I）与Triton B的水解产生了4a-spirohydantoin（II）与III一起作为主要产物，表明氢氧根离子的主要亲核攻击是在I的10a位置引发的。
• Visible Light-Induced Radical Cyclization of Ethyl 2-(<i>N</i>-Arylcarbamoyl)-2-Chloroiminoacetates: Synthesis of Quinoxalin-2(1<i>H</i>)-ones
  作者：Dianjun Li、Haichao Ma、Wei Yu

  DOI：10.1002/adsc.201500774

  日期：2015.11.16

  irradiation with Ru(phen)3Cl2 as photocatalyst can induce ethyl 2-(N-arylcarbamoyl)-2-chloroiminoacetates to undergo NCl cleavage to give α-(aminocarbonyl)iminyl radicals under an argon atmosphere. The subsequent cyclization of the thus formed iminyl radicals affords quinoxalin-2(1H)-one products in good yield in the presence of an inorganic base such as Na2CO3. The reactions proceeded very well even without

  本文揭示了用Ru（phen）3 Cl 2作为光催化剂的可见光照射可以诱导2-（N-芳基氨基甲酰基）-2-氯亚氨基乙酸乙酯在N2气氛下裂解为NCl并产生α-（氨基羰基）亚氨基自由基。在无机碱如Na 2 CO 3的存在下，由此形成的亚氨基自由基的随后环化以良好的产率提供了喹喔啉-2（1 H）-一产物。当使用DMF作为溶剂时，即使不使用光催化剂，反应也进行得非常好。这些协议为生成亚氨基自由基提供了一种新的简单方法，并且本文所述的反应构成了合成喹喔啉-2（1）的有效方法。H）-一阶导数。
• tert-Butyl Hypochlorite Induced Cyclization of Ethyl 2-(N-Aryl­carbamoyl)-2-iminoacetates
  作者：Ying Li、Wei Yu、Dianjun Li

  DOI：10.1055/s-0036-1588462

  日期：2017.9

  Strategies in Synthesis Abstract Ethyl 2-(N-arylcarbamoyl)-2-iminoacetates can be transformed into the corresponding quinoxalin-2-ones in high yield by using the oxidation system of tert-butyl hypochlorite, tetrabutylammonium iodide and tetrabutylammonium chloride. Oxygen exhibits a beneficial effect on the reaction. The reaction is proposed to follow an iminyl radical cyclization mechanism where az

  作为专题“现代合成中的环化策略”的一部分发布 抽象的 通过使用次氯酸叔丁基酯，碘化四丁基铵和氯化四丁基铵的氧化体系，可以将2-（N-芳基氨基甲酰基）-2-亚氨基乙酸乙酯乙酯高产率转化为相应的喹喔啉-2-酮。氧气对反应显示出有益的作用。提出该反应遵循亚氨基自由基环化机制，其中形成氮杂螺环己二烯基过氧自由基作为关键中间体。喹喔啉-2-酮通过同时进行的氧挤出和重排衍生自氮杂螺环己二烯基过氧自由基。 通过使用次氯酸叔丁基酯，碘化四丁基铵和氯化四丁基铵的氧化体系，可以将2-（N-芳基氨基甲酰基）-2-亚氨基乙酸乙酯乙酯高产率转化为相应的喹喔啉-2-酮。氧气对反应显示出有益的作用。提出该反应遵循亚氨基自由基环化机制，其中形成氮杂螺环己二烯基过氧自由基作为关键中间体。喹喔啉-2-酮通过同时进行的氧挤出和重排衍生自氮杂螺环己二烯基过氧自由基。
• Harayama, Takashi; Tezuka, Yasuhiro; Taga, Tooru, Journal of the Chemical Society. Perkin transactions I, 1987, p. 75 - 84
  作者：Harayama, Takashi、Tezuka, Yasuhiro、Taga, Tooru、Yoneda, Fumio

  DOI：——

  日期：——
• Ligand-free Pd(II)-catalyzed cyclization of α-chloroimino-N-arylamides to synthesis of quinoxalin-2(1H)-ones
  作者：Dianjun Li、Jinhui Yang、Xu Fan

  DOI：10.1016/j.tetlet.2020.152556

  日期：2020.11

  A ligand-free Pd(II)-catalyzed synthesis of quinoxalin-2(1H)-ones has been developed. Pd(TFA)(2) can induce ethyl 2-(N-arylcarbamoyl)-2-chloroiminoacetates to undergo cyclization to afford quinoxalin-2(1H)-one products in high yields in the presence of Na2CO3. This catalytic system is also effective to convert alpha-aryl-alpha-chloroimino-N-arylamides to the corresponding quinoxalin-2(1H)-one products via tandem N-Cl cleavage and N-arylation in moderate yields. The reaction described herein constitutes simple and effective approach towards quinoxalin-2(1H)-one derivatives. (C) 2020 Elsevier Ltd. All rights reserved.