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双环[2.2.2]辛烯酮的氧化裂解：解开α-二甲氧基羰基

Oxidative Scission of Bicyclo[2.2.2]octenones: Untying the α-Dimethoxycarbonyl.

作者信息

Yao Ting-Zhi, Tseng Yi-Cheng, Li Jia-Luo, Hou Deng-Lian, Chuang Gary Jing

机构信息

Department of Chemistry, Chung Yuan Christian University, Chung-Li 320314, Taiwan.

出版信息

J Org Chem. 2025 Feb 7;90(5):2126-2131. doi: 10.1021/acs.joc.4c02699. Epub 2025 Jan 28.

DOI:10.1021/acs.joc.4c02699
PMID:39874543
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11812015/
Abstract

This study explores the selective oxidative scission of bicyclo[2.2.2]octenones derived from masked -benzoquinones (MOBs). By employing the fragmentation of ketoximes and Schmidt-type reactions, we achieved the cleavage of α-dimethoxy carbonyl groups to yield highly functionalized cyclohexene frameworks, showcasing the expanding synthetic utility of bicyclo[2.2.2]octenones in complex organic synthesis. The methodologies developed are anticipated to contribute to advancements in organic and pharmaceutical chemistry.

摘要

本研究探索了源自掩蔽苯醌（MOBs）的双环[2.2.2]辛烯酮的选择性氧化裂解。通过利用酮肟的碎片化反应和施密特型反应，我们实现了α-二甲氧基羰基的裂解，生成了高度官能化的环己烯骨架，展示了双环[2.2.2]辛烯酮在复杂有机合成中不断扩大的合成效用。所开发的方法有望为有机化学和药物化学的发展做出贡献。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/b5930e077cbd/jo4c02699_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/24066eccd0d3/jo4c02699_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/ade58b755ccf/jo4c02699_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/fefb44c1e4b0/jo4c02699_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/525d2c484019/jo4c02699_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/b5930e077cbd/jo4c02699_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/24066eccd0d3/jo4c02699_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/ade58b755ccf/jo4c02699_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/fefb44c1e4b0/jo4c02699_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/525d2c484019/jo4c02699_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/b5930e077cbd/jo4c02699_0005.jpg

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本文引用的文献

1
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Molecules. 2024 Jan 25;29(3):595. doi: 10.3390/molecules29030595.
2
Acid-Promoted Cyclization of α-Azidobenzyl Ketones through C═N Bond Formation: Synthesis of 6-Substituted Quinoline Derivatives.通过形成C═N键实现酸促进的α-叠氮苄基酮环化反应：6-取代喹啉衍生物的合成
Org Lett. 2024 Jan 26;26(3):586-590. doi: 10.1021/acs.orglett.3c03697. Epub 2024 Jan 10.
3
Synthesis of -arylphenol derivatives acid-promoted rearrangement of cyclohexadienones.
Org Biomol Chem. 2023 Nov 1;21(42):8573-8578. doi: 10.1039/d3ob01363d.
4
Photoinduced Decarbonylative Rearrangement of Diazabicyclo[2.2.2]Octenones: A Photochemical Approach of Diazabicyclo[4.1.0]heptene Skeleton from Masked -Benzoquinone.
J Org Chem. 2023 Jan 20;88(2):1235-1244. doi: 10.1021/acs.joc.2c02373. Epub 2023 Jan 6.
5
Azoarene activation for Schmidt-type reaction and mechanistic insights.用于施密特型反应的偶氮芳烃的激活作用及机理研究。
Nat Commun. 2022 Dec 1;13(1):7393. doi: 10.1038/s41467-022-35141-4.
6
Chan-Lam Reaction and Lewis Acid Promoted 1,3-Rearrangement of N-O Bonds to Prepare -(2-Hydroxyaryl)pyridin-2-ones.
Org Lett. 2022 Jul 1;24(25):4675-4679. doi: 10.1021/acs.orglett.2c01827. Epub 2022 Jun 17.
7
Organophotoredox-catalyzed semipinacol rearrangement via radical-polar crossover.有机光氧化还原催化的通过自由基-极性交叉的半频哪醇重排。
Nat Commun. 2022 May 13;13(1):2684. doi: 10.1038/s41467-022-30395-4.
8
Radical-mediated rearrangements: past, present, and future.激进介导重排：过去、现在和未来。
Chem Soc Rev. 2021 Oct 18;50(20):11577-11613. doi: 10.1039/d1cs00529d.
9
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Angew Chem Int Ed Engl. 2021 Sep 1;60(36):19696-19700. doi: 10.1002/anie.202107080. Epub 2021 Jul 29.
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European J Org Chem. 2019 Mar 21;2019(11):2163-2171. doi: 10.1002/ejoc.201900231. Epub 2019 Mar 8.