ethyl (2Z)-2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)acetate | 86482-20-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (2Z)-2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)acetate
• 英文别名: (Z)-3-ethoxycarbonylmethylene-1,2,3,4-tetrahydro-2-quinoxalone；(Z)-ethyl 2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)acetate；ethyl (Z)-2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)acetate；(Z)-3-ethoxycarbonylmethylene-3,4-dihydro-2(1H)-quinoxalinone；2-ethoxycarbonylmethylene-3-oxo-1,2,3,4-tetrahydroquinoxaline；3-ethoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline；Ethyl 2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)acetate；ethyl (2Z)-2-(3-oxo-1,4-dihydroquinoxalin-2-ylidene)acetate
• CAS: 86482-20-4
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: SARMCVBXQHWZQN-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2Z)-2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)acetate 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以86%的产率得到furo<2,3-b>quinoxaline-3-carboxylic acid
  参考文献：
  名称：

  Kurasawa, Yoshihisa; Takada, Atsushi, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 10, p. 2871 - 2876

  摘要：

  DOI：
• 作为产物：
  描述：

  3-hydrazinocarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline 在 碳酸氢钠 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 ethyl (2Z)-2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)acetate
  参考文献：
  名称：

  Kurasawa, Yoshihisa; Ichikawa, Mitsugu; Takada, Atsushi, Heterocycles, 1983, vol. 20, # 2, p. 269 - 271

  摘要：

  DOI：

文献信息

• Introduction of a clean and promising protocol for the synthesis of β-amino-acrylates and 1,4-benzoheterocycles: an emerging innovation
  作者：Garima Choudhary、Rama Krishna Peddinti

  DOI：10.1039/c1gc15701a

  日期：——

  A highly efficient, elegant and simple procedure with exceptionally mild conditions has been proposed for the synthesis of β-amino-acrylate derivatives and an array of biologically and pharmaceutically active benzoheterocycles. The protocol offers a valuable alternative to known methods and will find applications in the field of green synthesis. The regio- and stereo-chemistry of the products were established by IR, NMR and single crystal X-ray analysis.

  提出了一种高效、优雅且简单的过程，用于合成β-氨基丙烯酸酯衍生物和一系列具有生物学及药物活性的苯并杂环化合物，条件极为温和。该方案为已知方法提供了一种有价值的替代方案，并将应用于绿色合成领域。产品的区域和立体化学性质通过红外光谱、核磁共振和单晶X射线分析得以确定。
• Hydroamination Reactions of Alkynes with<i>ortho</i>-Substituted Anilines in Ball Mills: Synthesis of Benzannulated N-Heterocycles by a Cascade Reaction
  作者：Maik Weiße、Markus Zille、Katharina Jacob、Robert Schmidt、Achim Stolle

  DOI：10.1002/chem.201406306

  日期：2015.4.20

  electrophilic alkynes and anilines with OH, NH, or SH groups in the ortho position. For the heterocycle formation, it was shown that several stress conditions were able to initiate the reaction in the solid state. Processing in a ball mill seemed to be advantageous over comminution with mortar and pestle with respect to process control. In the latter case, significant postreaction modification occurred during

  结果表明，在行星式球磨机中，邻位取代的苯胺易于与乙炔二羧酸二乙酯发生加氢胺化反应。分子间加氢反应与分子内闭环的顺序偶联被用于由易得的结构单元即邻位具有OH，NH或SH基团的亲电炔烃和苯胺合成苯并恶嗪，喹喔啉和苯并噻嗪位置。对于杂环的形成，已表明几种应力条件能够以固态引发反应。就过程控制而言，在球磨机中进行处理似乎比用研钵和研杵粉碎更为有利。在后一种情况下，固态分析期间发生了显着的反应后修饰。低温研磨证明对试剂的分子转化有不利影响。
• 2-Imidazolidinone benzofurans as unexpected outcome of the Lewis acid mediated Nenitzescu reaction
  作者：Tomas Horsten、Temitayo Omowumi Alegbejo Price、Luc Van Meervelt、Flavio da Silva Emery、Wim Dehaen

  DOI：10.1039/d1nj04965h

  日期：——

  The Lewis acid mediated Nenitzescu reaction with piperazinone enaminoesters surprisingly afforded rearranged 2-imidazolidinone 5-hydroxybenzofurans. The reaction was optimised and a scope study was performed. A one-pot two-step procedure was realised starting directly from 1,2-diaminoethane, diethyl acetylene dicarboxylate and 1,4-benzoquinone. A plausible reaction mechanism is proposed.

  Lewis酸介导的Nenitzescu与哌嗪酮烯胺酯的反应令人惊讶地得到重排的2-咪唑啉酮5-羟基苯并呋喃。优化反应并进行范围研究。直接从 1,2-二氨基乙烷、乙炔二羧酸二乙酯和 1,4-苯醌开始，实现了一锅两步法。提出了一种似是而非的反应机理。
• Reaction of Acylpyruvic Acids and Their Esters with N-(2-Aminophenyl)acetamide
  作者：E. E. Stepanova、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s1070428019030254

  日期：2019.3

  -oxobut-2-enoates, whose structure was confirmed by X-ray analysis. These compounds were formed as a result of condensation involving the primary amino group of N-(2-aminophenyl)acetamide at the most electrophilic C2=O carbonyl group of acylpyruvic acid or its ester. The obtained enamines underwent thermal heterocyclization to (Z)-3-(2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-ones having no substituent

  酰基丙酮酸及其酯与N-（2-氨基苯基）乙酰胺区域选择性反应，生成无环烯胺，取代了（Z）-2-[（（2-乙酰氨基苯基）氨基] -4-氧代丁-2-烯酸酯，其结构已通过X射线分析。这些化合物是通过缩合形成N-（2-氨基苯基）乙酰胺的伯氨基在酰基丙酮酸或其酯的最亲电的C 2＝ O羰基上形成的。将获得的烯胺热杂环化为（Z）-3-（2-氧代亚乙基）-3,4-二氢喹喔啉-2（1 H）-在N 1原子上没有取代基而不是预期的（Z）-1-乙酰基-3-（2-氧代亚乙基）-3,4-二氢喹喔啉-2（1 H）-那些。杂环化涉及酰胺和羧酸（酯）片段之间的分子内交换。所述的转化在温和的条件下发生，不需要催化剂或其他添加剂，因此符合“绿色化学”原理。从药物化学，药理学和精细有机合成的观点来看，这些产品可能是有趣的。
• Novel synthesis of dihydroquinoxaline, thiocyanatomaleate, uracil, pyridinium ylide, and S-aryl carbamimidothioate derivatives
  作者：Ali Monfared、Gholamhossein Khalili

  DOI：10.1007/s00706-022-02992-y

  日期：2022.12

  4-dihydroquinoxalin-2(1H)-ylidene)acetate, uracil, and thiocyanatomaleate derivatives have been prepared from substituted dihydroquinoxalines, benzylaminomaleates, and 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione in the presence of N-thiocyanatosuccinimide intermediate generated from NH4SCN with NCS at room temperature, respectively. Convenient synthesis of sulfur-containing compounds of pyridinium

  新型官能化烷基 ( Z )-2-(3-oxo-3,4-dihydroquinoxalin-2( 1H )-ylidene) 乙酸酯、尿嘧啶和硫氰酸基马来酸酯衍生物由取代的二氢喹喔啉、苄基氨基马来酸酯和 6-氨基马来酸酯制备而成。 1,3-二甲基嘧啶-2,4(1 H ,3 H )-二酮在N-硫氰酸基琥珀酰亚胺中间体的存在下分别由NH 4 SCN 和NCS 在室温下生成。描述了在无催化剂条件下以良好收率方便地合成吡啶鎓叶立德和S-芳基硫代氨基甲酸酯衍生物的含硫化合物。 图形概要