• 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

[1,2]-磷杂-Brook重排反应的最新进展

Recent Developments in the [1,2]-Phospha-Brook Rearrangement Reaction.

作者信息

Li Ning, Wu Qian, Huang Yu, Shi Enxue, Li Junchen

机构信息

State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China.

出版信息

Int J Mol Sci. 2025 Mar 27;26(7):3065. doi: 10.3390/ijms26073065.

DOI:10.3390/ijms26073065
PMID:40243753
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11989137/
Abstract

The [1,2]-phospha-Brook rearrangement serves as a powerful synthetic strategy that enables efficient carbonyl umpolung through phosphoryl group migration, providing direct access to α-hydroxyphosphoryl compounds-a privileged class of synthons with broad applications in organophosphorus chemistry, medicinal chemistry, and materials science. This review provides a comprehensive overview of recent progress in synthetic methodologies, possible mechanisms, and asymmetric transformations, highlighting key breakthroughs and future directions in this rapidly evolving field.

摘要

[1,2]-磷-Brook重排是一种强大的合成策略,它能够通过磷酰基迁移实现高效的羰基极性翻转,直接得到α-羟基磷酰基化合物——这是一类在有机磷化学、药物化学和材料科学中具有广泛应用的重要合成子。本综述全面概述了合成方法、可能的机理以及不对称转化方面的最新进展,突出了这个快速发展领域的关键突破和未来方向。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/8ec3a1cb183d/ijms-26-03065-g031.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/5012ecf55f4d/ijms-26-03065-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/c70b62a6c924/ijms-26-03065-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/92d3580689fa/ijms-26-03065-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/72d6f0d69c83/ijms-26-03065-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/0219ad6a9d32/ijms-26-03065-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/5605df862478/ijms-26-03065-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/539c443ab9ca/ijms-26-03065-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/bc640cc6fb3f/ijms-26-03065-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/750d25188724/ijms-26-03065-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/b842e7ac08e5/ijms-26-03065-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/aff14d170a67/ijms-26-03065-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/b3b9e63bb05d/ijms-26-03065-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/18c48eea795c/ijms-26-03065-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/649e47b53ec3/ijms-26-03065-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/8981fa13cefa/ijms-26-03065-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/9b4a1deba595/ijms-26-03065-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/6a4b765510d2/ijms-26-03065-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/88572c3a3d59/ijms-26-03065-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/ce3a562f8758/ijms-26-03065-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/addf1323058c/ijms-26-03065-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/ca080dbe1ed8/ijms-26-03065-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/5becc4024eb2/ijms-26-03065-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/0a51dc0b85b1/ijms-26-03065-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/76e08b5e4dc6/ijms-26-03065-g025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/025cd5818623/ijms-26-03065-g027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/3b77d8ac736b/ijms-26-03065-g028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/4226afcaf8fe/ijms-26-03065-g029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/8ec3a1cb183d/ijms-26-03065-g031.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/5012ecf55f4d/ijms-26-03065-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/c70b62a6c924/ijms-26-03065-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/92d3580689fa/ijms-26-03065-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/72d6f0d69c83/ijms-26-03065-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/0219ad6a9d32/ijms-26-03065-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/5605df862478/ijms-26-03065-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/539c443ab9ca/ijms-26-03065-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/bc640cc6fb3f/ijms-26-03065-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/750d25188724/ijms-26-03065-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/b842e7ac08e5/ijms-26-03065-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/aff14d170a67/ijms-26-03065-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/b3b9e63bb05d/ijms-26-03065-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/18c48eea795c/ijms-26-03065-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/649e47b53ec3/ijms-26-03065-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/8981fa13cefa/ijms-26-03065-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/9b4a1deba595/ijms-26-03065-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/6a4b765510d2/ijms-26-03065-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/88572c3a3d59/ijms-26-03065-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/ce3a562f8758/ijms-26-03065-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/addf1323058c/ijms-26-03065-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/ca080dbe1ed8/ijms-26-03065-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/5becc4024eb2/ijms-26-03065-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/0a51dc0b85b1/ijms-26-03065-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/76e08b5e4dc6/ijms-26-03065-g025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/025cd5818623/ijms-26-03065-g027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/3b77d8ac736b/ijms-26-03065-g028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/4226afcaf8fe/ijms-26-03065-g029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2e12/11989137/8ec3a1cb183d/ijms-26-03065-g031.jpg

相似文献

1
Recent Developments in the [1,2]-Phospha-Brook Rearrangement Reaction.[1,2]-磷杂-Brook重排反应的最新进展
Int J Mol Sci. 2025 Mar 27;26(7):3065. doi: 10.3390/ijms26073065.
2
Efficient Synthesis of Polysubstituted Pyrroles Based on [3+2] Cycloaddition Strategy Utilizing [1,2]-Phospha-Brook Rearrangement under Brønsted Base Catalysis.基于 Brønsted 碱催化下[1,2]-膦杂-Brook 重排的[3+2]环加成策略高效合成多取代吡咯。
Chemistry. 2018 Oct 12;24(57):15246-15253. doi: 10.1002/chem.201803809. Epub 2018 Oct 5.
3
Catalytic Generation of Benzyl Anions from Aryl Ketones Utilizing [1,2]-Phospha-Brook Rearrangement and Their Application to Synthesis of Tertiary Benzylic Alcohols.利用[1,2]-磷杂-Brook重排从芳基酮催化生成苄基阴离子及其在叔苄醇合成中的应用
Chemistry. 2024 Dec 10;30(69):e202402967. doi: 10.1002/chem.202402967. Epub 2024 Oct 16.
4
Novel Stereo-Induction Pattern in Pudovik Addition/Phospha-Brook Rearrangement Towards Chiral Trisubstituted Allenes.在向手性三取代丙二烯的普多维克加成/磷杂-布鲁克重排中新型立体诱导模式。
Angew Chem Int Ed Engl. 2024 May 27;63(22):e202403707. doi: 10.1002/anie.202403707. Epub 2024 Apr 12.
5
Stereoselective Reductive Coupling Reactions Utilizing [1,2]-Phospha-Brook Rearrangement: A Powerful Umpolung Approach.利用[1,2]-磷杂-Brook重排的立体选择性还原偶联反应:一种强大的极性翻转方法。
J Org Chem. 2023 Aug 4;88(15):10325-10338. doi: 10.1021/acs.joc.3c01055. Epub 2023 Jul 17.
6
Radical Brook rearrangement: past, present, and future.自由基布鲁克重排反应:过去、现在与未来。
Chem Soc Rev. 2025 Feb 17;54(4):1870-1904. doi: 10.1039/d4cs01275e.
7
Organocatalytic Arylation of α-Ketoesters Based on Umpolung Strategy: Phosphazene-Catalyzed S Ar Reaction Utilizing [1,2]-Phospha-Brook Rearrangement.基于反转策略的α-酮酯的有机催化芳基化反应:利用[1,2]-膦杂-Brook 重排的磷叶立德催化 S Ar 反应。
Chemistry. 2018 Sep 6;24(50):13110-13113. doi: 10.1002/chem.201803218. Epub 2018 Aug 13.
8
Formal Umpolung Addition of Phosphites to 2-Azaaryl Ketones under Chiral Brønsted Base Catalysis: Enantioselective Protonation Utilizing [1,2]-Phospha-Brook Rearrangement.在手性布朗斯特碱催化下亚磷酸酯对2-氮芳基酮的形式极性反转加成:利用[1,2]-磷-布鲁克重排的对映选择性质子化反应
Chemistry. 2022 Jul 26;28(42):e202201240. doi: 10.1002/chem.202201240. Epub 2022 Jun 10.
9
Synthesis of phenanthrene derivatives by intramolecular cyclization utilizing the [1,2]-phospha-Brook rearrangement catalyzed by a Brønsted base.利用布朗斯特碱催化的[1,2]-磷杂-Brook重排通过分子内环化合成菲衍生物。
Chemistry. 2015 Sep 1;21(36):12577-80. doi: 10.1002/chem.201501377.
10
Catalytic asymmetric synthesis of quaternary α-hydroxy trifluoromethyl phosphonate via chiral aluminum(III) catalyzed hydrophosphonylation of trifluoromethyl ketones.手性铝(III)催化三氟甲基酮的氢膦酰化反应合成季碳 α-手性三氟甲基膦酸酯的催化不对称合成。
Org Lett. 2010 Oct 1;12(19):4296-9. doi: 10.1021/ol101737b.

本文引用的文献

1
Umpolung Phosphorylation of Tyrosine via 1,2-Phospha-Brook Rearrangement.通过 1,2-膦酰-Brook 重排实现酪氨酸的反转磷酸化。
Org Lett. 2024 Oct 18;26(41):8827-8831. doi: 10.1021/acs.orglett.4c03223. Epub 2024 Oct 10.
2
Deciphering Asymmetric Brønsted Base-Aminocatalytic Mode in Pudovik/[1,2]-Phospha-Brook Rearrangement/Michael Cascade Reaction.解析普多维克反应/[1,2]-磷-布鲁克重排/迈克尔串联反应中的不对称布朗斯特碱-氨基催化模式
J Org Chem. 2024 Oct 4;89(19):14177-14182. doi: 10.1021/acs.joc.4c01570. Epub 2024 Sep 18.
3
Catalytic Generation of Benzyl Anions from Aryl Ketones Utilizing [1,2]-Phospha-Brook Rearrangement and Their Application to Synthesis of Tertiary Benzylic Alcohols.
利用[1,2]-磷杂-Brook重排从芳基酮催化生成苄基阴离子及其在叔苄醇合成中的应用
Chemistry. 2024 Dec 10;30(69):e202402967. doi: 10.1002/chem.202402967. Epub 2024 Oct 16.
4
Deoxygenative Hetero- and Carbofunctionalizations of Diarylketones.二芳基酮的脱氧杂官能化和碳官能化
J Org Chem. 2024 Jun 7;89(11):8157-8167. doi: 10.1021/acs.joc.4c00831. Epub 2024 May 10.
5
Novel Stereo-Induction Pattern in Pudovik Addition/Phospha-Brook Rearrangement Towards Chiral Trisubstituted Allenes.在向手性三取代丙二烯的普多维克加成/磷杂-布鲁克重排中新型立体诱导模式。
Angew Chem Int Ed Engl. 2024 May 27;63(22):e202403707. doi: 10.1002/anie.202403707. Epub 2024 Apr 12.
6
Sequential -Formed Kukhtin-Ramirez Adduct and P(NMe)-Catalyzed -Phosphination of α-Dicarbonyls with P(O)-H.顺序形成的库赫廷-拉米雷斯加合物以及P(NMe)催化的α-二羰基化合物与P(O)-H的磷酰化反应
Org Lett. 2023 Oct 27;25(42):7595-7600. doi: 10.1021/acs.orglett.3c02563. Epub 2023 Oct 13.
7
Chiral Lewis Acid-Catalyzed Asymmetric Multicomponent Michael Reaction through [1,2]-Phospha-Brook Rearrangement.通过[1,2]-磷-Brook重排实现的手性路易斯酸催化的不对称多组分迈克尔反应
Org Lett. 2023 Sep 1;25(34):6262-6266. doi: 10.1021/acs.orglett.3c02042. Epub 2023 Aug 21.
8
Stereoselective Reductive Coupling Reactions Utilizing [1,2]-Phospha-Brook Rearrangement: A Powerful Umpolung Approach.利用[1,2]-磷杂-Brook重排的立体选择性还原偶联反应:一种强大的极性翻转方法。
J Org Chem. 2023 Aug 4;88(15):10325-10338. doi: 10.1021/acs.joc.3c01055. Epub 2023 Jul 17.
9
Lewis acid-catalyzed Pudovik reaction-phospha-Brook rearrangement sequence to access phosphoric esters.通过路易斯酸催化的普多维克反应-磷杂布鲁克重排序列来合成磷酸酯。
Beilstein J Org Chem. 2022 Sep 9;18:1188-1194. doi: 10.3762/bjoc.18.123. eCollection 2022.
10
Catalytic Regio- and Enantioselective Protonation for the Synthesis of Chiral Allenes: Synergistic Effect of the Counterion and Water.用于合成手性丙二烯的催化区域和对映选择性质子化:抗衡离子与水的协同效应
Angew Chem Int Ed Engl. 2022 Jul 4;61(27):e202203650. doi: 10.1002/anie.202203650. Epub 2022 May 19.