1-aminocarbonyl-3-methyl-4-methoxycarbonyl-1,2-diaza-1,3-diene | 63160-41-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-aminocarbonyl-3-methyl-4-methoxycarbonyl-1,2-diaza-1,3-diene
• 英文别名: Methyl 3-[(E)-carbamoyldiazenyl]but-2-enoate；methyl 3-(carbamoyldiazenyl)but-2-enoate
• CAS: 63160-41-8
• 化学式: C₆H₉N₃O₃
• 分子量: 171.156
• InChiKey: ONMXXZGVXROBAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-aminocarbonyl-3-methyl-4-methoxycarbonyl-1,2-diaza-1,3-diene 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.1h， 生成 3-Methyl-6-oxo-1,6-dihydro-pyridazine-4,5-dicarboxylic acid 5-ethyl ester 4-methyl ester
  参考文献：
  名称：

  Easy Access to (E,Z )-β-Nitro-α,β-olefinated Hydrazones, 6-Oxo-1,6-dihydropyridazines, and 4-Chloro-1-aminopyrroles by Domino Reactions of 1,2-Diaza-1,3-butadienes with Halogen-Coactivated Methylene or Methine Compounds

  摘要：

  In the presence of a catalytic amount of sodium methoxide, 1-aminocarbonyl-1,2-diaza-1,3-butadienes react with bromonitromethane to give stereos electively beta-nitro-alpha,beta-olefinated hydrazones as E,Z stereoisomers. In the presence of a stoichiometric amount of sodium hydride, the same substrates with dialkyl halomalonates furnish the expected alpha,beta-olefinated hydrazones, and in the presence of a stoichiometric amount of sodium hydroxide, the unexpected dialkyl 3-methyl-6-oxo-1,6-dihydropyridazine-4,5-dicarboxylates are obtained in one pot by a domino process concluding in a [4 + 2] cyclization. alpha,beta-Olefinated hydrazones have been shown to be the possible intermediates in the formation of 1,6-dihydropyridazine derivatives. The domino reaction of 1-aminocarbonyl-1,2-diaza-1,3-butadienes with alpha,alpha-dichloroacetophenone produces directly alkyl 4-chloro-2(chloromethyl)-5-phenyl- or alkyl 4-chloro-2( methoxymethyl)-5-phenyl-1N-aminopyrrole-3-carboxylates as a consequence of [3 + 2] cyclization and chlorine transfer.

  DOI：

  10.1021/jo9912698

文献信息

• The Reaction of Meldrum's Acid and Its Derivatives with Conjugated Azoalkenes: A Convenient Route to 1-Amino-1<i>H</i>-pyrrol-2(3<i>H</i>)-ones
  作者：Antonio Arcadi、Orazio A. Attanasi、Zhiyuan Liao、Franco Serra-Zanetti

  DOI：10.1055/s-1994-25532

  日期：——

  The reaction of Meldrum's acid and its 5-substituted derivatives with conjugated azoalkenes in the presence of triethylamine produces, via 1,4-conjugate addition, corresponding hydrazones which undergo decarboxylative alcoholysis and simultaneous cyclization to give 3-unsubstituted and 3-monosubstituted 1-amino-1H-pyrrol-2-(3H)-ones respectively.

  在三乙胺存在下，Meldrum酸及其5-取代衍生物与共轭叠氮烯进行1,4-共�配加成反应，生成相应的腙，这些腙随后发生脱羧醇解反应并同步环化，分别形成3-未取代和3-单取代的1-氨基-1H-吡咯-2-(3H)-酮。
• Reaction of 1,2-Diaza-1,3-butadienes with Aminophosphorus Nucleophiles: A Practical Access to New Phosphorylated Pyrazolones
  作者：Orazio A. Attanasi、Graziano Baccolini、Carla Boga、Lucia De Crescentini、Gianluca Giorgi、Fabio Mantellini、Simona Nicolini

  DOI：10.1002/ejoc.200800856

  日期：2008.12

  The reaction of 1,2-diaza-1,3-butadienes with dibenzyl diisopropylphosphoramidite, methyl tetraisopropylphosphorodiamidite or tris(dimethylamino)phosphane under solvent-free conditions gave stable α-phosphoranylidene-hydrazones that, in turn, were transformed into the corresponding 5-oxo-4-phosphoranylidene-4,5-dihydro-1H-pyrazoles. X-ray diffraction analysis of one of these derivatives is reported

  1,2-二氮杂-1,3-丁二烯与二苄基二异丙基亚磷酰胺、甲基四异丙基亚磷酰胺或三（二甲氨基）膦在无溶剂条件下反应得到稳定的 α-亚膦基-腙，然后转化为相应的 5- oxo-4-phosphoranylidene-4,5-dihydro-1H-pyrazoles。报道了这些衍生物之一的 X 射线衍射分析。α-亚磷酰腙衍生自 1,2-二氮杂-1,3-丁二烯与二苄基二异丙基亚磷酰胺之间的反应，通过水解裂解转化为 (E)-腙-膦酸酯，可用于制备相应的 ( 3-oxo-2,3-dihydro-1H-pyrazol-4-yl)phosphonamidates。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009）
• On-Water Vinylogous Mukaiyama-Michael Addition of Heterocyclic 2-Silyloxydienes to 1,2-Diaza-1,3-dienes: One-Pot Three-Step Entry to Functionality-Rich Pyrroles
  作者：Lucia Battistini、Luca Dell'Amico、Andrea Sartori、Claudio Curti、Giorgio Pelosi、Giovanni Casiraghi、Orazio A. Attanasi、Gianfranco Favi、Franca Zanardi

  DOI：10.1002/adsc.201100296

  日期：2011.8

  prepared in good yields in a highly practical one-pot three-step procedure. The key reaction of this process, which involves an uninterrupted sequence of reactions on-water, is a diastereoselective vinylogous Mukaiyama–Michael addition reaction (VMMcR) of heterocyclic 2-silyloxydienes to 1,2-diaza-1,3-dienes mediated by water itself. Subsequent in situ addition of catalytic aqueous sodium carbonate promotes

  已经以高度实用的一锅三步法高产率地制备了稠密取代的吡咯羧酸酯。该过程的关键反应涉及水上不间断的反应序列，是水介导的杂环2-甲硅烷基氧二烯与1,2-二氮杂-1,3-二烯的非对映选择性乙烯基Mukaiyama-Michael加成反应（VMMcR）。本身。随后原位添加催化性碳酸钠水溶液可促进分子内氮杂-迈克尔加成，并具有最终的开环和芳构化作用。优越的使用水在VMMcR既是反应介质和启动子VIS-à-VIS 强调了常规路易斯酸在有机溶剂中的部署，这在反应速率，效率，立体选择性和整体实用性方面提供了最佳结果。
• Direct Access to Variously Substituted 2-Imino-4-thiazolines
  作者：Stefania Santeusanio、Orazio Attanasi、Gianfranco Favi、Paolino Filippone、Francesca Perrulli

  DOI：10.1055/s-0030-1258108

  日期：2010.7

  1,2-Diaza-1,3-dienes readily react as Michael acceptors with thiocyanic acid generated in situ from potassium thiocyanate. The acidic medium of the reaction promotes the intramolecular ring closure of the α-thiocyanato hydrazones allowing access to novel 2-imino-4-thiazolines functionalized at positions 3, 4, and 5 in a one-pot, high-yielding process.

  1,2-二氮-1,3-二烯很容易作为Michael受体与原位生成的硫氰酸反应，该反应的酸性介质促进了α-硫氰酸脲的内环化闭合，从而实现了一锅法、高收率地合成在3、4和5位功能化的新的2-亚氨基-4-噻唑啉。
• FeCl ₃ ‐Catalyzed Formal [3+2] Cyclodimerization of 4‐Carbonyl‐1,2‐diaza‐1,3‐dienes
  作者：Giacomo Mari、Matteo Corrieri、Lucia De Crescentini、Gianfranco Favi、Stefania Santeusanio、Fabio Mantellini

  DOI：10.1002/ejoc.202101046

  日期：2021.10.7

  An 1,2-diaza-1,3-diene's cyclodimerization that provides symmetrical fully substituted 1-amino pyrroles through an unusual formal [3+2] reaction is investigated. The study has demonstrated that the presence of electron withdrawing groups on the terminal carbon atom of the azo-ene system is crucial for the success of the reaction. The synthesis occurs with complete regioselectivity and requires a very

  研究了 1,2-二氮杂-1,3-二烯的环二聚反应，通过不寻常的正式 [3+2] 反应提供对称的完全取代的 1-氨基吡咯。研究表明，偶氮烯体系末端碳原子上吸电子基团的存在对反应的成功至关重要。该合成具有完全的区域选择性，需要非常简单的后处理程序。