ethyl 2-(benzo[d][1,3]dioxol-5-yl)-4-hydroxy-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate | 1415676-75-3

• 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 2-(benzo[d][1,3]dioxol-5-yl)-4-hydroxy-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate
• CAS: 1415676-75-3
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: DITHENCBUKFBCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  85.3
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  已腈 、 3,4-亚甲二氧基苄烯苯胺 、 ethyl 2-(benzo[d][1,3]dioxol-5-yl)-4-hydroxy-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate 以 甲醇 为溶剂， 反应 48.0h， 以85%的产率得到ethyl 2-(benzo[d][1,3]dioxol-5-yl)-4-((benzo[d][1,3]dioxol-5-ylmethyl)(2-oxo-2-(pentylamino)-1-phenylethyl)amino)-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Enols as Feasible Acid Components in the Ugi Condensation

  摘要：

  Heterocyclic enols are used for the first time as acid components in an Ugi-type multicomponent condensation. For that purpose, we have chosen enols containing a Michael acceptor, in order to facilitate an irreversible rearrangement of the primary Ugi adduct. The new four-component process leads readily and efficiently to heterocyclic enamines containing at least six elements of diversity.

  DOI：

  10.1021/ol302976g
• 作为产物：
  描述：

  3,4-亚甲二氧基苄烯苯胺 、 sodium diethylmalonate 在 硫酸 、 水 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以44%的产率得到ethyl 2-(benzo[d][1,3]dioxol-5-yl)-4-hydroxy-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Enols as Feasible Acid Components in the Ugi Condensation

  摘要：

  Heterocyclic enols are used for the first time as acid components in an Ugi-type multicomponent condensation. For that purpose, we have chosen enols containing a Michael acceptor, in order to facilitate an irreversible rearrangement of the primary Ugi adduct. The new four-component process leads readily and efficiently to heterocyclic enamines containing at least six elements of diversity.

  DOI：

  10.1021/ol302976g

文献信息

• 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。