dimethyl 1-((methoxycarbonyl)amino)-2,5-dimethyl-1H-pyrrole-3,4-dicarboxylate | 104954-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: dimethyl 1-((methoxycarbonyl)amino)-2,5-dimethyl-1H-pyrrole-3,4-dicarboxylate
• 英文别名: dimethyl 1-(methoxycarbonylamino)-2,5-dimethylpyrrole-3,4-dicarboxylate
• CAS: 104954-01-0
• 化学式: C₁₂H₁₆N₂O₆
• 分子量: 284.269
• InChiKey: LPFRQHKQKOTVKR-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168 °C
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  95.86
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  3,6-Dimethyl-4H-pyridazine-1,4,5-tricarboxylic acid trimethyl ester 在 三氟乙酸 作用下， 反应 2.0h， 以88%的产率得到dimethyl 1-((methoxycarbonyl)amino)-2,5-dimethyl-1H-pyrrole-3,4-dicarboxylate
  参考文献：
  名称：

  Reaction of Some 1,2-Diaza-1,3-butadienes with Activated Methine Compounds. A Straightforward Entry to 1,4-Dihydropyridazine, Pyridazine, and 4,5(4H,5H)-Cyclopropylpyrazole Derivatives

  摘要：

  1-Aminocarbonyl-1,2-diaza-1,3-butadienes with beta-tri- or beta-dicarbonyl compounds containing at least two keto functions give 1,4-dihydropyridazines, while hydrazone 1,4-adducts are obtained in the case of compounds containing one or no keto function. 1,4-Dihydropyridazines are transformed into pyridazines. The same substrates with 3-phenoxypentane-2,4-dione afford pyridazines. Surprisingly, 1-alkoxycarbonyl-1,2-diaza-1,3-butadiene with methyl 2-acetylacetoacetate produce 1-alkoxycarbonyl-4,5(4H,5H)-(alkoxycarbonylcyclopropyl)pyrazoles deriving from 1-alkoxycarbonyl-1,2-dihydropyridazine intermediates by ring contraction. These pyrazole derivatives with acetic acid show ring expansion to 1-alkoxycarbonyl-1,4-dihydropyridazines that can be converted into 1,4-dihydropyridazines with sodium hydroxide. 1-Alkoxycarbonyl-4,5(4H, 5H)-(alkoxycarbonylcyclopropyl)pyrazoles or 1-alkoxycarbonyl-1,4-dihydropyridazines with trifluoroacetic acid provide 1-aminopyrroles via 1-alkoxycarbonyl-1,4-dihydropyridazine intermediates in the case of pyrazoles. The X-ray crystal structure of 1-tert-butoxycarbonyl-3,5-dimethyl-4-methoxycarbonyl-4,5(4H,5H)-(methoxycarbonylcyclopropyl)-1H-pyrazole was determined.

  DOI：

  10.1021/jo9816515

文献信息

• 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。
• Attanasi, Orazio; Filippone, Paolino; Mei, Amedeo, Synthetic Communications, 1986, vol. 16, # 3, p. 343 - 352
  作者：Attanasi, Orazio、Filippone, Paolino、Mei, Amedeo、Serra-Zanetti, Franco

  DOI：——

  日期：——
• ATTANASI, O.;FILIPPONE, P.;MEI, A.;SERRA-ZANETTI, F., SYNTH. COMMUN., 1986, 16, N 3, 343-351
  作者：ATTANASI, O.、FILIPPONE, P.、MEI, A.、SERRA-ZANETTI, F.

  DOI：——

  日期：——