diethyl 2-(p-tolylamino)but-2-enedioate | 1397129-50-8

• 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: diethyl 2-(p-tolylamino)but-2-enedioate
• 英文别名: Diethyl 2-(4-methylanilino)but-2-enedioate；diethyl 2-(4-methylanilino)but-2-enedioate
• CAS: 1397129-50-8
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: WQFNZRQFMNCHRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(p-tolylamino)but-2-enedioate 在 polyphosphoric acid 作用下， 以 neat (no solvent) 为溶剂， 生成 ethyl 6-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate
  参考文献：
  名称：

  Facile synthesis of 4-quinolone derivatives via one-pot cascade reaction under transition-metal-free conditions

  摘要：

  A practical and efficient strategy has been described for the preparation of 4-quinolone derivatives. Using commercially available diethyl acetylenedicarboxylate and aromatic amines as starting materials, the synthetic protocol has been achieved and afforded the product via hydroamination at room temperature followed by PPA-catalyzed intramolecular ring closure. The products can be easily obtained in high yields. Conditions and mechanism of the reaction have also been investigated. This protocol is environmentally friendly and transition-metal-free, with advantages including short reaction time, convenient operation, and mild reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.04.060
• 作为产物：
  描述：

  乙烷,三氯氟- 、 丁炔二酸二乙酯 以 乙醇 为溶剂， 反应 0.5h， 生成 diethyl 2-(p-tolylamino)but-2-enedioate
  参考文献：
  名称：

  1-脯氨酸催化的高度官能化的多取代1,4-二氢吡啶的合成†

  摘要：

  高度精巧地通过L-合成了高度官能化的多取代1,4-二氢吡啶5。脯氨酸炔烃或炔烃1，胺2，β-二羰基化合物3和醛4在温和的条件下。MCR过程涉及加氢胺化/ Knoevenagel缩合/ Michael型加成/分子内环化过程，并导致形成1,4-二氢吡啶5。通过单晶X射线衍射确认了5ckaa的分子结构。该方法节能环保，可轻松获得各种多取代的多官能多官能1,4-二氢吡啶。

  DOI：

  10.1039/b914659h

文献信息

• One-Pot Multicomponent Mechanosynthesis of Polysubstituted <i>trans</i>-2,3-Dihydropyrroles and Pyrroles from Amines, Alkyne Esters, and Chalcones
  作者：Hui Xu、Hong-Wei Liu、Kuan Chen、Guan-Wu Wang

  DOI：10.1021/acs.joc.8b00665

  日期：2018.6.1

  one-pot multicomponent reaction of amines with alkyne esters and chalcones promoted by I2/PhI(OAc)2 has been developed under solvent-free ball-milling conditions to afford a variety of polysubstituted trans-2,3-dihydropyrroles in moderate to good yields. The present method features a short reaction time, mild reaction conditions, broad substrate scope, and feasibility of large-scale synthesis. Intriguingly

  在无溶剂球磨条件下，开发了一种由I 2 / PhI（OAc）2促进的胺与炔烃酯和查耳酮的高效，实用的一锅多组分反应，可提供多种多取代的反式-2,3-二氢吡咯中等至良好的产量。该方法具有反应时间短，反应条件温和，底物范围广，可大规模合成的特点。有趣的是，该方案还可以通过一锅法添加氧化剂来提供相应的合成上更具吸引力的吡咯。
• Novel One‐Pot Synthesis of Functionalized Quinolines from Isocyanides, Aniline, and Acetylene Dicarboxylate <i>via</i> Cu‐Catalyzed Intramolecular C─H Activation Reactions
  作者：Manijeh Nematpour、Elham Rezaee、Mehdi Jahani、Sayyed Abbas Tabatabai

  DOI：10.1002/jhet.3477

  日期：2019.4

  The one‐pot synthesis of a novel class of substituted quinoline derivatives with good yields is achieved via the Cu‐catalyzed intramolecular C─H activation reaction between isocyanides, aniline, and acetylene dicarboxylate in MeCN at room temperature. The existence of one‐pot conditions, availability of a starting material‐catalyst, the absence of column chromatography, and a high yield of products

  一类新的具有良好产率取代的喹啉衍生物的一锅合成实现通过在Cu催化的分子内C─H激活异腈，苯胺和二羧酸乙炔酯之间在MeCN在室温下反应。一锅法条件的存在，原料催化剂的可用性，不存在柱色谱法以及产物的高收率是该方法的优点。通过光谱（1 H NMR和13 C NMR，IR和EI-MS）并通过元素分析确认了结构。
• A three-component one-pot synthesis of penta-substituted pyrroles via ring opening of α-nitroepoxides
  作者：Donghong Zhao、Yue Zhu、Shanshan Guo、Wenteng Chen、Guolin Zhang、Yongping Yu

  DOI：10.1016/j.tet.2017.03.074

  日期：2017.5

  A novel and facile one-pot reaction has been developed to synthesize a variety of penta-substituted pyrroles from α-nitroepoxides, primary amines and dialkyl acetylenedicarboxylates under the conditions without catalyst. Furthermore, the controlled experiments has been performed and a possible mechanism has also been proposed.

  已经开发了新颖且简便的一锅反应，以在无催化剂的条件下由α-硝基环氧化物，伯胺和乙酰二羧酸二烷基酯合成多种五取代的吡咯。此外，已经进行了受控实验并且还提出了可能的机制。
• Efficient Synthesis of the Functionalized Spiro[indoline‐3,4′‐pyridine] via Four‐component Reaction
  作者：Jing Sun、Qun Wu、Lijuan Zhang、Chaoguo Yan

  DOI：10.1002/cjoc.201100657

  日期：2012.7

  An efficient synthetic procedure for the functionalized spiro[indoline‐3,4′‐pyridine] was developed via the four‐component reactions of arylamines, acetylenedicarboxylates, isatins and malononitrile with triethylamine as the base catalyst. The advantages of this reaction are using common starting material, mild reaction conditions, broad scope of reactants and operational simplicity.

  通过芳基胺，乙炔二羧酸酯，靛红和丙二腈与三乙胺为基础催化剂的四组分反应，开发了一种有效的合成功能化螺[吲哚啉-3,4'-吡啶]的方法。该反应的优点是使用普通的起始原料，温和的反应条件，广泛的反应物范围和操作简便性。
• TRIFLUOROACETIC ACID CATALYZED ONE-POT FOUR-COMPONENT DOMINO REACTION FOR THE SYNTHESIS OF SUBSTITUTED DIHYDRO 2-OXYPYRROLES
  作者：Mojtaba Lashkari、Malek Taher Maghsoodlou、Mahsa Karima、Mehrnoosh Kangani

  DOI：10.4067/s0717-97072018000103799

  日期：——

  Trifluoroacetic acid was applied as an efficient catalyst for the one-pot four-component synthesis of N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates via the domino reaction of amines, formaldehyde and dialkyl acetylenedicarboxylates at ambient temperature in methanol. This methodology includes number of advantages such as: short reaction time, clean work-up, use of inexpensive catalyst, high

  三氟乙酸是在环境温度下通过胺，甲醛和乙酰二羧酸二烷基酯的多米诺反应，作为一种有效的催化剂，用于一锅四组分合成N-芳基/烷基-3-氨基二氢吡咯-2-酮-4-羧酸酯。甲醇。该方法包括许多优点，例如：反应时间短，清洁后处理，使用廉价的催化剂，高收率和清洁后处理。该反应的后处理仅涉及过滤和用MeOH的简单洗涤步骤，并且不需要柱色谱法。