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Diels-Alder 环加成反应在可持续介质中的应用。

Diels-Alder Cycloaddition Reactions in Sustainable Media.

机构信息

University of Coimbra, Coimbra Chemistry Centre-Institute of Molecular Sciences and Department of Chemistry, 3004-535 Coimbra, Portugal.

出版信息

Molecules. 2022 Feb 15;27(4):1304. doi: 10.3390/molecules27041304.

DOI:10.3390/molecules27041304
PMID:35209094
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8876200/
Abstract

Diels-Alder cycloaddition reaction is one of the most powerful strategies for the construction of six-membered carbocyclic and heterocyclic systems, in most cases with high regio- and stereoselectivity. In this review, an insight into the most relevant advances on sustainable Diels-Alder reactions since 2010 is provided. Various environmentally benign solvent systems are discussed, namely bio-based derived solvents (such as glycerol and gluconic acid), polyethylene glycol, deep eutectic solvents, supercritical carbon dioxide, water and water-based aqueous systems. Issues such as method's scope, efficiency, selectivity and reaction mechanism, as well as sustainability, advantages and limitations of these reaction media, are addressed.

摘要

Diels-Alder 环加成反应是构建六元碳环和杂环系统的最强大策略之一,在大多数情况下具有高区域和立体选择性。本文综述了 2010 年以来可持续 Diels-Alder 反应的最新进展。讨论了各种环境友好型溶剂体系,即生物基衍生溶剂(如甘油和葡萄糖酸)、聚乙二醇、深共晶溶剂、超临界二氧化碳、水和水基水体系。讨论了这些反应介质的方法范围、效率、选择性和反应机理以及可持续性、优点和局限性等问题。

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Front Chem. 2023 Aug 8;11:1229669. doi: 10.3389/fchem.2023.1229669. eCollection 2023.
5
Antibacterial-Based Hydrogel Coatings and Their Application in the Biomedical Field-A Review.基于抗菌剂的水凝胶涂层及其在生物医学领域的应用——综述
J Funct Biomater. 2023 Apr 25;14(5):243. doi: 10.3390/jfb14050243.
6
Pushing Photochemistry into Water: Acceleration of the Di-π-Methane Rearrangement and the Paternó-Büchi Reaction "On-Water".将光化学推向水中:促进二-π-甲烷重排和 Paternó-Büchi 反应“在水中”。
Chemistry. 2023 Feb 10;29(9):e202203203. doi: 10.1002/chem.202203203. Epub 2022 Dec 27.
7
Opioid Antagonists from the Orvinol Series as Potential Reversal Agents for Opioid Overdose.奥啡诺系列阿片受体拮抗剂作为阿片类药物过量解毒的潜在逆转剂。
ACS Chem Neurosci. 2022 Nov 2;13(21):3108-3117. doi: 10.1021/acschemneuro.2c00464. Epub 2022 Oct 12.
新型低共熔溶剂对室温下狄尔斯-阿尔德反应内/外型比例的影响
ACS Omega. 2021 Jul 22;6(30):19392-19399. doi: 10.1021/acsomega.1c00980. eCollection 2021 Aug 3.
4
Eutectics: formation, properties, and applications.低共熔物:形成、性质和应用。
Chem Soc Rev. 2021 Aug 2;50(15):8596-8638. doi: 10.1039/d1cs00404b.
5
Organocatalytic Strategies for the Development of the Enantioselective Inverse-electron-demand Hetero-Diels-Alder Reaction.有机催化策略在对映选择性逆电子需求杂狄尔斯-阿尔德反应发展中的应用。
Chemistry. 2021 Sep 1;27(49):12509-12520. doi: 10.1002/chem.202101696. Epub 2021 Jul 13.
6
Fabrication of self-healing pectin/chitosan hybrid hydrogel via Diels-Alder reactions for drug delivery with high swelling property, pH-responsiveness, and cytocompatibility.通过狄尔斯-阿尔德反应制备具有高溶胀性、pH响应性和细胞相容性的用于药物递送的自愈合果胶/壳聚糖杂化水凝胶。
Carbohydr Polym. 2021 Sep 15;268:118244. doi: 10.1016/j.carbpol.2021.118244. Epub 2021 May 24.
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Deep Eutectic Solvents: A Review of Fundamentals and Applications.深共熔溶剂:基础与应用综述。
Chem Rev. 2021 Feb 10;121(3):1232-1285. doi: 10.1021/acs.chemrev.0c00385. Epub 2020 Dec 14.
8
Anise Essential Oil as a Sustainable Substrate in the Multicomponent Double Povarov Reaction for Julolidine Synthesis.茴香油作为可持续基质在多组分双重 Povarov 反应中用于合成 Julolidine。
J Org Chem. 2020 Dec 4;85(23):15622-15630. doi: 10.1021/acs.joc.0c02459. Epub 2020 Nov 11.
9
Solid-supported DNA for asymmetric synthesis: a stepping-stone toward practical applications.用于不对称合成的固相支持DNA:迈向实际应用的垫脚石。
Biomater Sci. 2013 Oct 28;1(10):1034-1036. doi: 10.1039/c3bm60134j. Epub 2013 Jul 10.
10
Investigation of the Diels-Alder reaction as a cross-linking mechanism for degradable poly(ethylene glycol) based hydrogels.研究狄尔斯-阿尔德反应作为基于可降解聚乙二醇水凝胶的交联机制。
J Mater Chem B. 2013 Oct 7;1(37):4855-4864. doi: 10.1039/c3tb20831a. Epub 2013 Aug 15.