Suppr超能文献

无环扭曲酰胺。

Acyclic Twisted Amides.

机构信息

Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.

College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Additives for China National Light Industry, Shaanxi University of Science and Technology, Xi'an 710021, China.

出版信息

Chem Rev. 2021 Oct 27;121(20):12746-12783. doi: 10.1021/acs.chemrev.1c00225. Epub 2021 Aug 18.

Abstract

In this contribution, we provide a comprehensive overview of acyclic twisted amides, covering the literature since 1993 (the year of the first recognized report on acyclic twisted amides) through June 2020. The review focuses on classes of acyclic twisted amides and their key structural properties, such as amide bond twist and nitrogen pyramidalization, which are primarily responsible for disrupting to π* conjugation. Through discussing acyclic twisted amides in comparison with the classic bridged lactams and conformationally restricted cyclic fused amides, the reader is provided with an overview of amidic distortion that results in novel conformational features of acyclic amides that can be exploited in various fields of chemistry ranging from organic synthesis and polymers to biochemistry and structural chemistry and the current position of acyclic twisted amides in modern chemistry.

摘要

在本综述中,我们全面概述了非循环扭曲酰胺,涵盖了自 1993 年(第一个被认可的非循环扭曲酰胺报道的年份)至 2020 年 6 月的文献。综述重点介绍了非循环扭曲酰胺的类别及其关键结构特性,如酰胺键扭曲和氮原子三角锥化,这些特性主要负责破坏酰胺键到π*共轭。通过将非循环扭曲酰胺与经典的桥连内酰胺和构象受限的环状稠合酰胺进行比较,读者可以了解酰胺键扭曲导致非循环酰胺产生新颖的构象特征,这些特征可应用于从有机合成和聚合物到生物化学和结构化学等化学领域,以及非循环扭曲酰胺在现代化学中的当前地位。

相似文献

1
Acyclic Twisted Amides.
Chem Rev. 2021 Oct 27;121(20):12746-12783. doi: 10.1021/acs.chemrev.1c00225. Epub 2021 Aug 18.
2
Reliable determination of amidicity in acyclic amides and lactams.
J Org Chem. 2012 Jul 6;77(13):5492-502. doi: 10.1021/jo300347k. Epub 2012 Jun 14.
3
Chemistry of Bridged Lactams: Recent Developments.
Molecules. 2019 Jan 12;24(2):274. doi: 10.3390/molecules24020274.
7
Twisted Amides: From Obscurity to Broadly Useful Transition-Metal-Catalyzed Reactions by N-C Amide Bond Activation.
Chemistry. 2017 May 29;23(30):7157-7173. doi: 10.1002/chem.201605012. Epub 2017 Feb 20.
9
Electrophilicity Scale of Activated Amides: O NMR and N NMR Chemical Shifts of Acyclic Twisted Amides in N-C(O) Cross-Coupling.
Chemistry. 2020 Dec 9;26(69):16246-16250. doi: 10.1002/chem.202003213. Epub 2020 Nov 11.
10
The Most Twisted Acyclic Amides: Structures and Reactivity.
Org Lett. 2018 Dec 21;20(24):7771-7774. doi: 10.1021/acs.orglett.8b03175. Epub 2018 Dec 10.

引用本文的文献

1
Insertion of anthranilyl unit into inert amides: A facile route to oligoamides and cyclic peptides.
Sci Adv. 2025 Jun 27;11(26):eadw0465. doi: 10.1126/sciadv.adw0465. Epub 2025 Jun 25.
2
Catalyst-Free Direct Hydrocarbonation of Terminal Alkynes Toward E-Alkene Substituted Stabilized Sulfoxonium Ylides.
Adv Sci (Weinh). 2025 Jun;12(22):e2417362. doi: 10.1002/advs.202417362. Epub 2025 Apr 2.
3
Towards the activity of twisted acyclic amides.
RSC Adv. 2025 Mar 24;15(11):8207-8212. doi: 10.1039/d5ra00229j. eCollection 2025 Mar 17.
4
Isoselenourea-Catalyzed Enantioselective Pyrazolo-Heterocycle Synthesis Enabled by Self-Correcting Amide and Ester Acylation.
Angew Chem Int Ed Engl. 2025 May;64(19):e202425305. doi: 10.1002/anie.202425305. Epub 2025 Mar 31.
5
Tuning the steric hindrance of alkylamines: a predictive model of steric editing of planar amines.
Chem Sci. 2024 Jul 11;15(33):13405-13414. doi: 10.1039/d4sc03873h. eCollection 2024 Aug 22.
6
Mechanistic insights on C(acyl)-N functionalisation mediated by late transition metals.
Dalton Trans. 2024 Dec 3;53(47):18803-18818. doi: 10.1039/d4dt01829j.
7
Challenges and Breakthroughs in Selective Amide Activation.
Angew Chem Weinheim Bergstr Ger. 2022 Dec 5;134(49):e202212213. doi: 10.1002/ange.202212213. Epub 2022 Nov 2.
10
Amide N-C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling.
SynOpen. 2023 Feb;7(1):88-101. doi: 10.1055/a-2035-6733. Epub 2023 Mar 6.

本文引用的文献

1
Decarboxylative Photocyclization:  Synthesis of Benzopyrrolizidines and Macrocyclic Lactones.
J Org Chem. 1999 Jul 9;64(14):5213-5217. doi: 10.1021/jo990390b.
2
Electrophilicity Scale of Activated Amides: O NMR and N NMR Chemical Shifts of Acyclic Twisted Amides in N-C(O) Cross-Coupling.
Chemistry. 2020 Dec 9;26(69):16246-16250. doi: 10.1002/chem.202003213. Epub 2020 Nov 11.
3
Selective Decarbonylation via Transition-Metal-Catalyzed Carbon-Carbon Bond Cleavage.
Chem Rev. 2021 Jan 13;121(1):365-411. doi: 10.1021/acs.chemrev.0c00153. Epub 2020 Jun 16.
4
-Acylcarbazoles and -Acylindoles: Electronically Activated Amides for N-C(O) Cross-Coupling by N to Ar Conjugation Switch.
Org Lett. 2020 Jun 19;22(12):4703-4709. doi: 10.1021/acs.orglett.0c01488. Epub 2020 Jun 1.
5
Enhanced reactivity of twisted amides inside a molecular cage.
Nat Chem. 2020 Jun;12(6):574-578. doi: 10.1038/s41557-020-0455-y. Epub 2020 Apr 20.
6
Conformational preference of bicyclic β-amino acid dipeptides.
Chirality. 2020 Jun;32(6):790-807. doi: 10.1002/chir.23220. Epub 2020 Apr 1.
7
8
Silyl Radical Mediated Cross-Electrophile Coupling of -Acyl-imides with Alkyl Bromides under Photoredox/Nickel Dual Catalysis.
Org Lett. 2020 Mar 20;22(6):2240-2245. doi: 10.1021/acs.orglett.0c00442. Epub 2020 Mar 9.
9
Peptide-based short single β-strand mimics without hydrogen bonding or aggregation.
Chem Commun (Camb). 2020 Feb 4;56(10):1573-1576. doi: 10.1039/c9cc08378b.
10
Transition-Metal-Free Activation of Amides by N-C Bond Cleavage.
Chem Rec. 2020 Jul;20(7):649-659. doi: 10.1002/tcr.201900072. Epub 2019 Dec 13.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验