ethyl 1,2-diphenyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate | 131189-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: ethyl 1,2-diphenyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: ethyl 4-hydroxy-5-oxo-1,2-diphenyl-2,5-dihydro-1H-pyrrole-3-carboxylate；1,5-diphenyl-4-ethoxycarbonyl-3-hydroxy-3-pyrroline-2-one；ethyl 4-hydroxy-5-oxo-1,2-diphenyl-2H-pyrrole-3-carboxylate
• CAS: 131189-25-8
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: NHWAAZXZONZXPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1,2-diphenyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate 在 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 Ethyl 5-ethoxy-4-methoxy-1,2-diphenylpyrrole-3-carboxylate
  参考文献：
  名称：

  Synthesis of 2,3-Dialkoxy-1H-pyrrole via Reduction of Dioxopyrroline with Sodium Hydrosulfite

  摘要：

  Reduction of IH-pyrrole-2,3-dione (3 and 7) with sodium hydrosulfite took place selectively in a 1,4-manner. Methylation of the product with diazomethane gave 1,5-dihydro-3-methoxy-2H-pyrrol-2-one (5 and 8) in good yield. Treatment of the methyl ether (5 or 8) with triethyloxonium tetrafluoroborate caused ethylation of the lactam carbonyl with concomitant deprotonation to give 2,3-dialkoxy-1H-pyrrole (9). This conversion provides a simple synthetic method of 2,3-dialkoxypyrroles.

  DOI：

  10.3987/com-93-6479
• 作为产物：
  描述：

  4-ethoxycarbonyl-1,5-diphenyl-1H-pyrrole-2,3-dione 在 sodium disulfite 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 生成 ethyl 1,2-diphenyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Synthesis of 2,3-Dialkoxy-1H-pyrrole via Reduction of Dioxopyrroline with Sodium Hydrosulfite

  摘要：

  Reduction of IH-pyrrole-2,3-dione (3 and 7) with sodium hydrosulfite took place selectively in a 1,4-manner. Methylation of the product with diazomethane gave 1,5-dihydro-3-methoxy-2H-pyrrol-2-one (5 and 8) in good yield. Treatment of the methyl ether (5 or 8) with triethyloxonium tetrafluoroborate caused ethylation of the lactam carbonyl with concomitant deprotonation to give 2,3-dialkoxy-1H-pyrrole (9). This conversion provides a simple synthetic method of 2,3-dialkoxypyrroles.

  DOI：

  10.3987/com-93-6479

文献信息

• Visible light-promoted synthesis of pyrrolidinone derivatives <i>via</i> Rose Bengal as a photoredox catalyst and their photophysical studies
  作者：Arup Dutta、Mostofa A. Rohman、Ridaphun Nongrum、Aiborlang Thongni、Sivaprasad Mitra、Rishanlang Nongkhlaw

  DOI：10.1039/d1nj00343g

  日期：——

  Herein, we report an intramolecular radical cyclization reaction towards the synthesis of pyrrolidinone derivatives via metal-free photoredox catalysis under irradiation from blue LEDs. Some of the remarkable features of this protocol include synthetic efficiency, green reaction profile, easy isolation of products and short reaction time. The photophysical properties of synthesized compounds were investigated

  在本文中，我们报道了在蓝色LED辐射下通过无金属的光氧化还原催化合成吡咯烷酮衍生物的分子内自由基环化反应。该协议的一些显着特征包括合成效率，绿色反应谱，易于分离的产物和较短的反应时间。通过固态和时间分辨荧光光谱法研究了合成化合物的光物理性质。结果表明，它们的光谱调谐以及大的斯托克斯位移和高活性荧光发射具有广阔的前景，因此表明这些分子支架可以作为光电器件的生物学应用和开发的有效探针。
• Selective Synthesis of 3-Substituted Pyrrolidinones by Enol-Passerini and Anomalous Enol-Passerini Condensations
  作者：Ana G. Neo、Carlos F. Marcos

  DOI：10.1021/acs.orglett.8b01462

  日期：2018.7.6

  the reaction conditions. These new transformations have proven to be a convenient alternative for the synthesis of biologically relevant pyrrolidinones containing peptidic or pseudo-peptidic groups on carbon 3. More importantly, this work attests to the utility of heterocyclic enols containing conjugated electron-withdrawing groups as useful reagents in isocyanide-based multicomponent reactions.

  根据反应条件，烯醇首次与醛和异氰化物缩合使用，以选择性地产生三或假四组分加合物。这些新的转化方法已证明是合成碳3上含有肽基或伪肽基团的生物学相关吡咯烷酮的便捷替代方法。更重要的是，这项工作证明了含有共轭吸电子基团的杂环烯醇作为有用的试剂可用于合成。基于异氰酸酯的多组分反应。
• An Efficient Synthesis of Pyrrolidinone Derivatives in the Presence of 1,1′-Butylenebis(3-sulfo-3H-imidazol-1-ium) Chloride
  作者：Nader Ghaffari Khaligh、Kim Foong Chong、Taraneh Mihankhah、Salam Titinchi、Mohd Rafie Johan、Juan Joon Ching

  DOI：10.1071/ch18246

  日期：——

  as a sulfonic acid-functionalized ionic liquid was demonstrated for the synthesis of pyrrolidinone derivatives under mild conditions. The electronic effect of substituents on aniline derivatives was investigated. Further, a study on the structure–activity relationship of ionic liquids containing sulfonic groups for the synthesis of ethyl-2-(4-chlorophenyl)-4-hydroxy-5-oxo-1-(p-tolyl)-2,5-dihydro-1H

  证明了1,1'-丁烯双（3-磺基-3 H-咪唑-1-基）氯化物作为磺酸官能化离子液体的催化效率在温和条件下合成了吡咯烷酮衍生物。研究了取代基对苯胺衍生物的电子效应。此外，对含磺酸基离子液体合成乙基-2-（4-氯苯基）-4-羟基-5-氧代-5-氧代-1-（对甲苯基）-2,5-的构效关系的研究在最佳条件下进行了二氢-1 H-吡咯-3-羧酸酯的合成。结果表明，具有两个具有碳间隔基的磺酸或咪唑部分的离子液体的催化性能优于具有一个没有碳间隔基的磺酸或咪唑部分的离子液体。
• Green one-pot multicomponent synthesis of pyrrolidinones using planetary ball milling process under solvent-free conditions
  作者：Nader Ghaffari Khaligh、Taraneh Mihankhah、Mohd Rafie Johan

  DOI：10.1080/00397911.2019.1601225

  日期：2019.5.19

  novel and efficient protocol for the synthesis of pyrrolidinones using catalytic loading of 1,1'-butylenebis(3-sulfo-3H-imidazol-1-ium) hydrogen sulfate as a recyclable Brönsted acid ionic liquid through ball milling process at room temperature under solvent-free conditions. The developed method provides good to excellent yields of various pyrrolidinones in environmentally friendly conditions. Furthermore

  摘要 本文提出了一种新型有效的合成吡咯烷酮的方案，该方案使用催化负载 1,1'-丁烯双（3-磺基-3H-咪唑-1-鎓）硫酸氢盐作为可回收的布朗斯台德酸离子液体，通过球磨工艺在室温下无溶剂条件下。所开发的方法在环境友好的条件下提供了各种吡咯烷酮的良好收率。此外，这种高效的协议将一锅多组分反应的合成优势与机械化学过程的生态效益和便利性相结合。图形概要
• Synthesis of pyrrolidinone derivatives from aniline, an aldehyde and diethyl acetylenedicarboxylate in an ethanolic citric acid solution under ultrasound irradiation
  作者：Hamideh Ahankar、Ali Ramazani、Katarzyna Ślepokura、Tadeusz Lis、Sang Woo Joo

  DOI：10.1039/c6gc00157b

  日期：——

  In this study, we reported a simple and efficient route for the one-pot sonochemical synthesis of substituted 3-pyrrolin-2-ones by citric acid as an additive.

  在这项研究中，我们报告了一种简单有效的途径，可通过柠檬酸作为添加剂一锅超声化学合成取代的3-吡咯啉-2-酮。