1-丁基-2-甲基-5-苯基-1H-吡咯-3-羧酸乙酯 | 101781-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-丁基-2-甲基-5-苯基-1H-吡咯-3-羧酸乙酯
• 英文名称: ethyl 1-butyl-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
• 英文别名: Ethyl 1-butyl-2-methyl-5-phenylpyrrole-3-carboxylate；ethyl 1-butyl-2-methyl-5-phenylpyrrole-3-carboxylate
• CAS: 101781-93-5
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: QHFIEZZDDSMZRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙酮肟 在 copper(l) iodide 、 manganese(III) triacetate dihydrate 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 1-丁基-2-甲基-5-苯基-1H-吡咯-3-羧酸乙酯
  参考文献：
  名称：

  Direct Oxidative Coupling of Enamides and 1,3-Dicarbonyl Compounds: A Facile and Versatile Approach to Dihydrofurans, Furans, Pyrroles, and Dicarbonyl Enamides

  摘要：

  An efficient manganese(III)-mediated oxidative coupling reaction between a-aryl enamides and 1,3-dicarbonyl compounds has been developed. A series of dihydrofurans and dicarbonyl enamides were synthesized in moderate to good yields. Moreover, these dihydrofurans could be readily transformed into the corresponding furans and pyrroles via the Paal-Knorr reaction.

  DOI：

  10.1021/ol503009f

文献信息

• Three-component access to pyrroles promoted by the CAN–silver nitrate system under high-speed vibration milling conditions: a generalization of the Hantzsch pyrrole synthesis
  作者：Verónica Estévez、Mercedes Villacampa、J. Carlos Menéndez

  DOI：10.1039/c2cc38099d

  日期：——

  A sequential multicomponent process involving the high-speed vibration milling of ketones with N-iodosuccinimide and p-toluenesulfonic acid, followed by addition of a mixture of primary amines, β-dicarbonyl compounds, cerium(IV) ammonium nitrate and silver nitrate afforded polysubstituted, functionalized pyrroles. This one-pot, solid-state process can be considered as the coupling of an α-iodoketone preparation with a general version of the classical Hantzsch pyrrole synthesis.

  一种顺序多组分过程，涉及酮与N-碘代琥珀酰亚胺和邻甲苯磺酸的高速振动研磨，随后加入混合的伯胺、β-二羰基化合物、铈(IV)硝酸铵和硝酸银，得到多取代、功能化的吡咯。这种一步法、固态过程可视为α-碘代酮制备与经典Hantzsch吡咯合成通法的结合。
• 微波辐射一步合成取代的吡咯-3-甲酸酯化合物 的方法
  申请人：齐齐哈尔大学

  公开号：CN103408481B

  公开（公告）日：2016-01-20

  微波辐射一步合成取代的吡咯-3-甲酸酯化合物的方法，本发明涉及取代的吡咯-3-甲酸酯化合物的合成方法。本发明是要解决现有的取代的吡咯-3-甲酸酯化合物的合成方法要分步进行，操作复杂的技术问题。本方法：将取代的α-溴代苯乙酮、取代的氨基化合物和取代的乙酰乙酸酯加入到单口烧瓶中，在微波反应器的微波功率为190～450W、温度为20～60℃的条件下反应，产物经分离、干燥、浓缩后进行重结晶，得到取代的吡咯-3-甲酸酯化合物。本方法没有中间体产物的处理分离纯化的操作，无需加入溶剂，反应时间仅为10～120min，原料易得，操作简单，产物的纯度大于95%。
• Microwave-Assisted One-Pot Synthesis of N-Substituted 2-Methyl-1H-pyrrole-3-carboxylate Derivatives without Catalyst and Solvent
  作者：Bing Zhao、Wei Kan、Tao Jing、Xiao-hong Zhang、Yong-jie Zheng、Lin Chen

  DOI：10.3987/com-15-13340

  日期：——

  An efficient one-pot synthetic method for the N-substituted 2-methyl-1H-pyrrole-3-carboxylate derivatives has been accomplished via a microwave irradiation MCRs of various alpha-bromoacetophenone, amines, and ethyl acetoacetate without any solvent and catalyst. This approach provides a convenient one pot method for the synthesis of N-substituted 2-methyl-1H-pyrrole-3-carboxylate derivatives.
• Direct Oxidative Coupling of Enamides and 1,3-Dicarbonyl Compounds: A Facile and Versatile Approach to Dihydrofurans, Furans, Pyrroles, and Dicarbonyl Enamides
  作者：Pan Li、Jingjing Zhao、Chungu Xia、Fuwei Li

  DOI：10.1021/ol503009f

  日期：2014.11.21

  An efficient manganese(III)-mediated oxidative coupling reaction between a-aryl enamides and 1,3-dicarbonyl compounds has been developed. A series of dihydrofurans and dicarbonyl enamides were synthesized in moderate to good yields. Moreover, these dihydrofurans could be readily transformed into the corresponding furans and pyrroles via the Paal-Knorr reaction.