• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

以羟基离子液体为促进剂,1,4 - 二氮杂双环[2.2.2]辛烷(DABCO)催化醛与氰基乙酸乙酯的Knoevenagel缩合反应。

DABCO-catalyzed Knoevenagel condensation of aldehydes with ethyl cyanoacetate using hydroxy ionic liquid as a promoter.

作者信息

Meng Dan, Qiao Yongsheng, Wang Xin, Wen Wei, Zhao Sanhu

机构信息

School Chemistry and Material Science, Shanxi Normal University Linfen 041001 Shanxi China

Department of Chemistry, Xinzhou Teachers University Xinzhou 034000 Shanxi China.

出版信息

RSC Adv. 2018 Aug 28;8(53):30180-30185. doi: 10.1039/c8ra06506c. eCollection 2018 Aug 24.

DOI:10.1039/c8ra06506c
PMID:35546849
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9085423/
Abstract

-(2-Hydroxy-ethyl)-pyridinium chloride ([HyEtPy]Cl) was synthesized and explored as a novel promoter for 1,4-diazabicyclo [2.2.2] octane (DABCO)-catalyzed Knoevenagel condensation reactions, which showed better catalytic activity compared to other ionic liquid (IL) that had no hydroxyl group attached to the IL scaffold. The effect of hydrogen bond formation between the hydroxyl group of [HyEtPy]Cl and the carbonyl group of aldehyde played an important role in the Knoevenagel condensation reaction. In the [HyEtPy]Cl-HO-DABCO composite system, Knoevenagel condensation reactions proceeded smoothly and cleanly, and the corresponding Knoevenagel condensation products were obtained in good to excellent yields in all cases examined. This protocol provides a versatile solvent-catalyst system, which has notable advantages such as being eco-friendly, ease of work-up and convenient reuse of the ionic liquid.

摘要

合成了氯化(2-羟乙基)吡啶鎓([HyEtPy]Cl),并将其作为一种新型促进剂用于1,4-二氮杂双环[2.2.2]辛烷(DABCO)催化的Knoevenagel缩合反应,与其他在离子液体骨架上未连接羟基的离子液体相比,它表现出更好的催化活性。[HyEtPy]Cl的羟基与醛的羰基之间形成氢键的作用在Knoevenagel缩合反应中起着重要作用。在[HyEtPy]Cl-HO-DABCO复合体系中,Knoevenagel缩合反应顺利且干净地进行,在所有考察的情况下,相应的Knoevenagel缩合产物均以良好至优异的产率得到。该方法提供了一种通用的溶剂-催化剂体系,具有环保、后处理简便以及离子液体可方便重复使用等显著优点。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5862/9085423/7d5dfd4ec987/c8ra06506c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5862/9085423/bcd4a3692d8d/c8ra06506c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5862/9085423/7d5dfd4ec987/c8ra06506c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5862/9085423/bcd4a3692d8d/c8ra06506c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5862/9085423/7d5dfd4ec987/c8ra06506c-s2.jpg

相似文献

1
DABCO-catalyzed Knoevenagel condensation of aldehydes with ethyl cyanoacetate using hydroxy ionic liquid as a promoter.以羟基离子液体为促进剂,1,4 - 二氮杂双环[2.2.2]辛烷(DABCO)催化醛与氰基乙酸乙酯的Knoevenagel缩合反应。
RSC Adv. 2018 Aug 28;8(53):30180-30185. doi: 10.1039/c8ra06506c. eCollection 2018 Aug 24.
2
Novel Pyridinium Based Ionic Liquid Promoter for Aqueous Knoevenagel Condensation: Green and Efficient Synthesis of New Derivatives with Their Anticancer Evaluation.新型吡啶基离子液体促进剂在水相 Knoevenagel 缩合反应中的应用:新型衍生物的绿色高效合成及其抗癌评价。
Molecules. 2022 May 4;27(9):2940. doi: 10.3390/molecules27092940.
3
Schiff base structured acid-base cooperative dual sites in an ionic solid catalyst lead to efficient heterogeneous knoevenagel condensations.席夫碱基结构的酸碱协同双功能点存在于离子固体催化剂中,从而导致高效的非均相 Knoevenagel 缩合反应。
Chemistry. 2012 Oct 1;18(40):12773-82. doi: 10.1002/chem.201201338. Epub 2012 Aug 21.
4
Synthesis of Dihydropyrimidinones (DHPMs) and Hexahydro Xanthene Catalyzed by 1,4-Diazabicyclo [2.2.2] Octane Triflate Under Solvent-Free Condition.1,4-二氮杂双环[2.2.2]辛烷三氟甲磺酸盐在无溶剂条件下催化合成二氢嘧啶酮(DHPMs)和六氢呫吨
Curr Org Synth. 2019;16(5):776-786. doi: 10.2174/1570179415666181113154232.
5
Layered double hydroxide anchored ionic liquids as amphiphilic heterogeneous catalysts for the Knoevenagel condensation reaction.层状双氢氧化物负载离子液体作为用于Knoevenagel缩合反应的两亲性多相催化剂。
Dalton Trans. 2018 Feb 27;47(9):3059-3067. doi: 10.1039/c7dt03665e.
6
Convenient synthesis of polyfunctional dihydrothiophenes with tandem reaction of 1,3-thiazolidinedione, aldehyde, arylamine and ethyl cyanoacetate.方便地合成具有 1,3-噻唑烷二酮、醛、芳胺和氰基乙酸乙酯串联反应的多功能二氢噻吩。
Mol Divers. 2011 Feb;15(1):115-23. doi: 10.1007/s11030-010-9278-x. Epub 2010 Sep 17.
7
DABCO Catalyzed Synthesis of Xanthene Derivatives in Aqueous Media.1,4-二氮杂双环[2.2.2]辛烷催化在水介质中合成呫吨衍生物
ISRN Org Chem. 2013 Mar 18;2013:526173. doi: 10.1155/2013/526173. eCollection 2013.
8
Molybdenum Oxide Nanoparticles as Recyclable Heterogeneous Catalyst for Synthesis of Arylidene Ethyl Cyanoacetates.氧化钼纳米粒子作为可回收的多相催化剂用于合成芳甲叉乙基氰乙酸酯。
J Nanosci Nanotechnol. 2019 Sep 1;19(9):5965-5973. doi: 10.1166/jnn.2019.16571.
9
Green Synthesis of Electrophilic Alkenes Using a Magnesium Catalyst under Aqueous Conditions and Mechanistic Insights by Density Functional Theory.在水相条件下使用镁催化剂亲电烯烃的绿色合成及基于密度泛函理论的机理研究
J Org Chem. 2023 Dec 15;88(24):16829-16844. doi: 10.1021/acs.joc.3c01540. Epub 2023 Dec 1.
10
Classical Keggin Intercalated into Layered Double Hydroxides: Facile Preparation and Catalytic Efficiency in Knoevenagel Condensation Reactions.插层到层状双氢氧化物中的经典Keggin结构:Knoevenagel缩合反应中的简便制备及催化效率
Chemistry. 2015 Oct 12;21(42):14862-70. doi: 10.1002/chem.201501953. Epub 2015 Sep 4.

引用本文的文献

1
Nitrogen Enriched Tröger's Base Polymers of Intrinsic Microporosity for Heterogeneous Catalysis.用于多相催化的富氮固有微孔性特罗格碱聚合物
ACS Appl Polym Mater. 2024 Dec 18;7(1):220-233. doi: 10.1021/acsapm.4c02952. eCollection 2025 Jan 10.
2
Extending the Carbon Chain Length of Carbohydrate-Derived 5-Substituted-2-furaldehydes by Condensing with Active Methylene Compounds under Organocatalytic Conditions.在有机催化条件下,通过与活性亚甲基化合物缩合来延长碳水化合物衍生的5-取代-2-糠醛的碳链长度
ACS Omega. 2024 Sep 6;9(37):38648-38657. doi: 10.1021/acsomega.4c04261. eCollection 2024 Sep 17.
3
Novel Pyridinium Based Ionic Liquid Promoter for Aqueous Knoevenagel Condensation: Green and Efficient Synthesis of New Derivatives with Their Anticancer Evaluation.

本文引用的文献

1
Microporous polyurethane material for size selective heterogeneous catalysis of the Knoevenagel reaction.
Chem Commun (Camb). 2016 Jun 14;52(50):7834-7. doi: 10.1039/c6cc02578a.
2
Fast Knoevenagel Condensations Catalyzed by an Artificial Schiff-Base-Forming Enzyme.人工席夫碱形成酶催化的快速 Knoevenagel 缩合反应。
J Am Chem Soc. 2016 Jun 8;138(22):6972-4. doi: 10.1021/jacs.6b00816. Epub 2016 May 31.
3
Aldehyde-Tagged Zirconium Metal-Organic Frameworks: a Versatile Platform for Postsynthetic Modification.醛基标记的锆基金属有机框架:后合成修饰的通用平台
新型吡啶基离子液体促进剂在水相 Knoevenagel 缩合反应中的应用:新型衍生物的绿色高效合成及其抗癌评价。
Molecules. 2022 May 4;27(9):2940. doi: 10.3390/molecules27092940.
4
AgCO containing magnetic nanocomposite as a powerful and recoverable catalyst for Knoevenagel condensation.载银磁性纳米复合材料作为一种高效、可回收的 Knoevenagel 缩合反应催化剂。
Sci Rep. 2021 Sep 21;11(1):18736. doi: 10.1038/s41598-021-98287-z.
5
Three in One: The Versatility of Hydrogen Bonding Interaction in Halide Salts with Hydroxy-Functionalized Pyridinium Cations.三效合一:羟基功能化吡啶𬭩阳离子卤化物盐中氢键相互作用的多功能性。
Chemphyschem. 2021 Sep 15;22(18):1850-1856. doi: 10.1002/cphc.202100424. Epub 2021 Aug 4.
6
New dicationic DABCO-based ionic liquids: a scalable metal-free one-pot synthesis of bis-2-amino-5-arylidenethiazol-4-ones.新型基于1,4-二氮杂二环[2.2.2]辛烷的双阳离子离子液体:一种可扩展的无金属一锅法合成双-2-氨基-5-芳亚甲基噻唑-4-酮。
R Soc Open Sci. 2019 Jul 24;6(7):190997. doi: 10.1098/rsos.190997. eCollection 2019 Jul.
Inorg Chem. 2016 May 16;55(10):4701-3. doi: 10.1021/acs.inorgchem.6b00598. Epub 2016 May 2.
4
Base-free Knoevenagel condensation catalyzed by copper metal surfaces.铜金属表面催化的无碱克诺文纳格尔缩合反应
Chem Commun (Camb). 2015 Jul 7;51(53):10695-8. doi: 10.1039/c5cc02541a. Epub 2015 Jun 5.
5
A bifunctional, site-isolated metal-organic framework-based tandem catalyst.一种双功能、位点隔离的金属有机框架基串联催化剂。
Inorg Chem. 2015 Apr 6;54(7):3134-8. doi: 10.1021/ic502316v. Epub 2015 Mar 18.
6
Chiral primary amine catalyzed asymmetric Michael addition of malononitrile to α-substituted vinyl ketone.手性伯胺催化丙二腈对α-取代乙烯基酮的不对称迈克尔加成反应。
Org Lett. 2015 Jan 16;17(2):382-5. doi: 10.1021/ol503566a. Epub 2014 Dec 31.
7
Asymmetric α-photoalkylation of β-ketocarbonyls by primary amine catalysis: facile access to acyclic all-carbon quaternary stereocenters.通过伯胺催化的β-酮羰基不对称α-光烷基化反应:轻松构建非环全碳季碳立体中心。
J Am Chem Soc. 2014 Oct 22;136(42):14642-5. doi: 10.1021/ja508605a. Epub 2014 Sep 19.
8
Ionic liquids and ultrasound in combination: synergies and challenges.离子液体与超声联合:协同与挑战。
Chem Soc Rev. 2014 Dec 7;43(23):8132-49. doi: 10.1039/c4cs00193a. Epub 2014 Sep 8.
9
Core-shell palladium nanoparticle@metal-organic frameworks as multifunctional catalysts for cascade reactions.核壳钯纳米粒子@金属有机骨架作为级联反应的多功能催化剂。
J Am Chem Soc. 2014 Feb 5;136(5):1738-41. doi: 10.1021/ja411468e. Epub 2014 Jan 27.
10
Organocatalytic Knoevenagel condensations by means of carbamic acid ammonium salts.通过碳酸铵盐实现有机催化的 Knoevenagel 缩合反应。
Org Lett. 2013 Apr 19;15(8):1854-7. doi: 10.1021/ol400462d. Epub 2013 Apr 8.