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通过X@RONa催化的氧化还原链式反应快速获取类异戊二烯醌。

Rapid Access to Isoprenoid Quinones through X@RONa-Catalyzed Redox Chain Reaction.

作者信息

Zhang Zining, Gu Huanchao, Cao Dun-Xu, Li Zhi

机构信息

School of Physical Science and Technology, ShanghaiTech University, 393 Middle Huaxia Road, Pudong District, Shanghai 201210, China.

出版信息

J Am Chem Soc. 2024 Oct 23;146(42):29064-29071. doi: 10.1021/jacs.4c10470. Epub 2024 Oct 9.

DOI:10.1021/jacs.4c10470
PMID:39384527
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11669094/
Abstract

Dodecameric sodium alkoxide clusters encaging a halide anion (X@RONa) were shown to be C-C bond formation catalysts in the redox chain reaction of quinones. With up to 30 mol % -decanol as the catalyst and stoichiometric base NaH, a great number of chemically sensitive isoprenoid quinones, including health-relevant Coenzyme Q and Vitamin K family compounds, were easily made in one step from their parent quinones and polyprenyl halide. The X@RONa clusters and possible cluster-derived intermediates were studied by characterization techniques, control experiments, and theory. The X@RONa clusters likely facilitated the C-alkylation step by preventing O-alkylation, promoting dissociation of halide from the alkyl chain, and transporting hydride into the nonpolar solvent.

摘要

包裹卤化物阴离子的十二聚醇钠簇合物（X@RONa）在醌的氧化还原链反应中被证明是碳-碳键形成催化剂。以高达30 mol%的癸醇作为催化剂和化学计量的碱氢化钠，大量对化学敏感的类异戊二烯醌，包括与健康相关的辅酶Q和维生素K家族化合物，很容易从它们的母体醌和聚异戊二烯卤化物一步合成。通过表征技术、对照实验和理论研究了X@RONa簇合物以及可能由簇合物衍生的中间体。X@RONa簇合物可能通过防止氧烷基化、促进卤化物从烷基链上解离以及将氢化物传输到非极性溶剂中，促进了碳烷基化步骤。

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本文引用的文献

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Synthesis of natural polyprenols for the production of biological prenylquinones and tocochromanols.用于生产生物异戊二烯醌和生育三烯酚的天然聚戊烯醇的合成。
RSC Adv. 2023 Jul 31;13(33):23122-23129. doi: 10.1039/d3ra02872k. eCollection 2023 Jul 26.
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Chemistry of Lipoquinones: Properties, Synthesis, and Membrane Location of Ubiquinones, Plastoquinones, and Menaquinones.
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Int J Mol Sci. 2022 Oct 25;23(21):12856. doi: 10.3390/ijms232112856.
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Endohedral Mixed Aggregates: Sodium Alkoxide Cages with Organic or Inorganic Central Anions and Variable Hull.内嵌混合聚集体：含有有机或无机中心阴离子及可变外壳的醇钠笼状物
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