ethyl 1-benzyl-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate | 3652-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1-benzyl-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
• 英文别名: Ethyl 1-benzyl-2-methyl-5-phenyl-1h-pyrrole-3-carboxylate；ethyl 1-benzyl-2-methyl-5-phenylpyrrole-3-carboxylate
• CAS: 3652-45-7
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: GDTWAJWDQRPZIW-UHFFFAOYSA-N

物化性质

• 熔点：
  164 °C
• 沸点：
  457.5±33.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 1-benzyl-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-benzyl-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Arylpiperazine-containing pyrrole 3-carboxamide derivatives targeting serotonin 5-HT2A, 5-HT2C, and the serotonin transporter as a potential antidepressant

  摘要：

  Arylpiperzine-containing pyrrole 3-carboxamide derivatives were synthesized and evaluated as novel antidepressant compounds. The various analogues were efficiently prepared and bio-assayed for binding to 5-HT2A, 5-HT2C receptor, and 5-HT transporter. Based on their in vitro and in vivo activities as well as selectivity over other neurotransmitter receptors and PK profiles, 33 and 34 were identified as lead compounds. Consequently, this pyrrole series of compounds appears to be promising enough to warrant further investigation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.093
• 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 ethyl 1-benzyl-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
  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

• One-Step Continuous Flow Synthesis of Highly Substituted Pyrrole-3-carboxylic Acid Derivatives via in Situ Hydrolysis of <i>tert-</i>Butyl Esters
  作者：Ananda Herath、Nicholas D. P. Cosford

  DOI：10.1021/ol102216x

  日期：2010.11.19

  one-step, continuous flow synthesis of pyrrole-3-carboxylic acids directly from tert-butyl acetoacetates, amines, and 2-bromoketones is reported. The HBr generated as a byproduct in the Hantzsch reaction was utilized in the flow method to hydrolyze the t-butyl esters in situ to provide the corresponding acids in a single microreactor. The protocol was used in the multistep synthesis of pyrrole-3-carboxamides

  报道了直接从乙酰乙酸叔丁酯、胺和 2-溴酮合成吡咯-3-羧酸的第一步连续流动合成。在流动法中利用在 Hantzsch 反应中作为副产物产生的 HBr原位水解叔丁酯，以在单个微反应器中提供相应的酸。该协议用于 pyrrole-3-carboxamides 的多步合成，包括两种 CB1 反向激动剂，在单个连续过程中直接从市售起始材料中合成。
• 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。
• Sonochemically assisted synthesis of N-substituted pyrroles catalyzed by ZnO nanoparticles under solvent-free conditions
  作者：Ashraf S Shahvelayati、Maryam Sabbaghan、Solmaz Banihashem

  DOI：10.1007/s00706-016-1904-6

  日期：2017.6

  AbstractAn efficient and rapid synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from a one-pot multicomponent reaction of amines, 1,3-dicarbonyl compounds, and α-haloketones in the presence of ZnO nanoparticles catalyst under ultrasonic irradiation and solvent-free conditions is described. Graphical abstract

  摘要在超声波辐射和溶剂作用下，在ZnO纳米颗粒催化剂存在下，由胺，1,3-二羰基化合物和α-卤代烃的一锅多组分反应快速高效地合成1,2,3,5-四取代的吡咯衍生物描述了无条件。 图形概要
• Divergent and Synergistic Photocatalysis: Hydro- and Oxoalkylation of Vinyl Arenes for the Stereoselective Synthesis of Cyclopentanols via a Formal [4+1]-Annulation of 1,3-Dicarbonyls
  作者：Narenderreddy Katta、Quan-Qing Zhao、Tirtha Mandal、Oliver Reiser

  DOI：10.1021/acscatal.2c04736

  日期：2022.11.18

  are initiated through the formation of polarity-reversed C-centered-radical intermediates at the active methylene center of 1,3-dicarbonyls via direct photocatalytic C–H bond transformations. The oxoalkylation of alkenes is achieved under aerobic conditions via a Cu(II)-photomediated rebound mechanism, while the corresponding hydroalkylation becomes possible under a nitrogen atmosphere by the combination

  描述了 1,3-二羰基的可控发散反应性，这使得乙烯基芳烃的有效加氢和氧代烷基化成为可能。两种反应途径都是通过极性反转C的形成启动的通过直接光催化 C-H 键转换在 1,3-二羰基的活性亚甲基中心生成中心自由基中间体。烯烃的氧代烷基化在有氧条件下通过 Cu(II)-光介导的回弹机制实现，而相应的加氢烷基化在氮气气氛下通过 4CzIPN 和 Brønsted 碱的组合成为可能。这些不同方案的广度在药物和天然产物的后期修饰以及将产物转化为各种杂环化合物（如吡啶、吡咯或呋喃）中得到证明。此外，这两种催化模式可以协同组合，在正式的[4+1]-环化过程中立体选择性构建环戊醇衍生物。
• 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.