• 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

通过卤氟代反应及相关反应合成新型含氟结构单元。

Synthesis of novel fluorinated building blocks via halofluorination and related reactions.

作者信息

Remete Attila Márió, Novák Tamás T, Nonn Melinda, Haukka Matti, Fülöp Ferenc, Kiss Loránd

机构信息

Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.

Interdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.

出版信息

Beilstein J Org Chem. 2020 Oct 16;16:2562-2575. doi: 10.3762/bjoc.16.208. eCollection 2020.

DOI:10.3762/bjoc.16.208
PMID:33133288
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7590628/
Abstract

A study exploring halofluorination and fluoroselenation of some cyclic olefins, such as diesters, imides, and lactams with varied functionalization patterns and different structural architectures is described. The synthetic methodologies were based on electrophilic activation through halonium ions of the ring olefin bonds, followed by nucleophilic fluorination with Deoxo-Fluor. The fluorine-containing products thus obtained were subjected to elimination reactions, yielding various fluorine-containing small-molecular entities.

摘要

本文描述了一项关于一些环状烯烃（如具有不同官能化模式和不同结构架构的二酯、酰亚胺和内酰胺）的卤氟化和氟硒化的研究。合成方法基于通过环烯烃键的卤鎓离子进行亲电活化，然后用Deoxo-Fluor进行亲核氟化。由此得到的含氟产物进行消除反应，生成各种含氟小分子实体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/1193f4b59eba/Beilstein_J_Org_Chem-16-2562-g027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/b154cb1ee4dd/Beilstein_J_Org_Chem-16-2562-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/5b0ac3cd2f26/Beilstein_J_Org_Chem-16-2562-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/68888bb448a6/Beilstein_J_Org_Chem-16-2562-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/63060265973d/Beilstein_J_Org_Chem-16-2562-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/4fd46761b8d9/Beilstein_J_Org_Chem-16-2562-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/301d295ff711/Beilstein_J_Org_Chem-16-2562-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/78c50b82c7ee/Beilstein_J_Org_Chem-16-2562-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/74e2be560258/Beilstein_J_Org_Chem-16-2562-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/7a7178f8d5cc/Beilstein_J_Org_Chem-16-2562-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/66a2c9b3e67d/Beilstein_J_Org_Chem-16-2562-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/369bf6f817ae/Beilstein_J_Org_Chem-16-2562-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/d7541abb5c7c/Beilstein_J_Org_Chem-16-2562-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/395aeb1689ba/Beilstein_J_Org_Chem-16-2562-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/882c500347d7/Beilstein_J_Org_Chem-16-2562-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/4794118c1e65/Beilstein_J_Org_Chem-16-2562-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/d8e01d4c6fc6/Beilstein_J_Org_Chem-16-2562-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/2ef81610f3a7/Beilstein_J_Org_Chem-16-2562-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/51314c7cc909/Beilstein_J_Org_Chem-16-2562-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/fb9380664762/Beilstein_J_Org_Chem-16-2562-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/54474cea240a/Beilstein_J_Org_Chem-16-2562-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/6ac22099f2d6/Beilstein_J_Org_Chem-16-2562-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/0869aac553b6/Beilstein_J_Org_Chem-16-2562-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/fbb52aff29eb/Beilstein_J_Org_Chem-16-2562-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/60345cb9ffab/Beilstein_J_Org_Chem-16-2562-g025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/cb2911572b5f/Beilstein_J_Org_Chem-16-2562-g026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/1193f4b59eba/Beilstein_J_Org_Chem-16-2562-g027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/b154cb1ee4dd/Beilstein_J_Org_Chem-16-2562-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/5b0ac3cd2f26/Beilstein_J_Org_Chem-16-2562-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/68888bb448a6/Beilstein_J_Org_Chem-16-2562-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/63060265973d/Beilstein_J_Org_Chem-16-2562-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/4fd46761b8d9/Beilstein_J_Org_Chem-16-2562-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/301d295ff711/Beilstein_J_Org_Chem-16-2562-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/78c50b82c7ee/Beilstein_J_Org_Chem-16-2562-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/74e2be560258/Beilstein_J_Org_Chem-16-2562-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/7a7178f8d5cc/Beilstein_J_Org_Chem-16-2562-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/66a2c9b3e67d/Beilstein_J_Org_Chem-16-2562-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/369bf6f817ae/Beilstein_J_Org_Chem-16-2562-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/d7541abb5c7c/Beilstein_J_Org_Chem-16-2562-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/395aeb1689ba/Beilstein_J_Org_Chem-16-2562-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/882c500347d7/Beilstein_J_Org_Chem-16-2562-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/4794118c1e65/Beilstein_J_Org_Chem-16-2562-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/d8e01d4c6fc6/Beilstein_J_Org_Chem-16-2562-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/2ef81610f3a7/Beilstein_J_Org_Chem-16-2562-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/51314c7cc909/Beilstein_J_Org_Chem-16-2562-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/fb9380664762/Beilstein_J_Org_Chem-16-2562-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/54474cea240a/Beilstein_J_Org_Chem-16-2562-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/6ac22099f2d6/Beilstein_J_Org_Chem-16-2562-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/0869aac553b6/Beilstein_J_Org_Chem-16-2562-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/fbb52aff29eb/Beilstein_J_Org_Chem-16-2562-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/60345cb9ffab/Beilstein_J_Org_Chem-16-2562-g025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/cb2911572b5f/Beilstein_J_Org_Chem-16-2562-g026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a5/7590628/1193f4b59eba/Beilstein_J_Org_Chem-16-2562-g027.jpg

相似文献

1
Synthesis of novel fluorinated building blocks via halofluorination and related reactions.通过卤氟代反应及相关反应合成新型含氟结构单元。
Beilstein J Org Chem. 2020 Oct 16;16:2562-2575. doi: 10.3762/bjoc.16.208. eCollection 2020.
2
Fluorine-Retentive Strategies for the Functionalization of -Difluoroalkenes.用于双氟烯烃官能化的氟保留策略。
Synthesis (Stuttg). 2021 Nov;53(21):3935-3950. doi: 10.1055/a-1547-9270.
3
Developments in fluorocyclization methodologies.氟环化方法学的发展。
Future Med Chem. 2009 Aug;1(5):847-63. doi: 10.4155/fmc.09.47.
4
Recent Progress in the Selective Fluorinations of Some Functionalized Cycloalkenes.一些官能化环烯烃的选择性氟化反应的最新进展。
Chem Rec. 2022 Sep;22(9):e202200130. doi: 10.1002/tcr.202200130. Epub 2022 Jun 9.
5
Fluorinated Cycloalkyl Building Blocks for Drug Discovery.氟代环烷基砌块在药物发现中的应用
ChemMedChem. 2022 Nov 4;17(21):e202200365. doi: 10.1002/cmdc.202200365. Epub 2022 Oct 5.
6
Diastereoselective synthesis of 2,3,4,5,6-pentafluoroheptanes.2,3,4,5,6-五氟庚烷的非对映选择性合成。
J Org Chem. 2009 Sep 18;74(18):7168-71. doi: 10.1021/jo901360e.
7
[Stereoselective Synthesis of Multi-substituted Fluoro-β-lactams and Their Conversion to Fluorinated β-Amino Acid Core].[多取代氟代β-内酰胺的立体选择性合成及其向氟化β-氨基酸核心的转化]
Yakugaku Zasshi. 2015;135(11):1245-53. doi: 10.1248/yakushi.15-00201.
8
Fluorine and Gold: A Fruitful Partnership.氟与金：相得益彰。
Chem Rev. 2016 Oct 12;116(19):11924-11966. doi: 10.1021/acs.chemrev.6b00203. Epub 2016 Aug 22.
9
Asymmetric fluorocyclizations of alkenes.不对称氟环化反应。
Acc Chem Res. 2014 Dec 16;47(12):3560-70. doi: 10.1021/ar500282z. Epub 2014 Nov 7.
10
Electrophilic fluorination of organosilanes.有机硅烷的亲电氟化反应。
Org Biomol Chem. 2006 Jan 7;4(1):26-32. doi: 10.1039/b513399h. Epub 2005 Nov 23.

本文引用的文献

1
Recent advances in the synthesis of functionalised monofluorinated compounds.近年来，功能化单氟化合物的合成取得了新进展。
Chem Commun (Camb). 2018 Aug 28;54(70):9706-9725. doi: 10.1039/c8cc05181j.
2
Picking One out of Three: Selective Single C-F Activation in Trifluoromethyl Groups.三选一：三氟甲基中 C-F 的选择性单键活化。
Chemistry. 2018 Oct 1;24(55):14572-14582. doi: 10.1002/chem.201801702. Epub 2018 Jul 30.
3
Benzylic Functionalisation of Phenyl all-cis-2,3,5,6-Tetrafluorocyclohexane Provides Access to New Organofluorine Building Blocks.
苄基化全顺式-2,3,5,6-四氟环己基苯提供了新的有机氟砌块。
Chemistry. 2018 Sep 6;24(50):13290-13296. doi: 10.1002/chem.201802166. Epub 2018 Jul 31.
4
Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence.一些高度官能化环烷烃的氟化反应：化学选择性与底物依赖性
Beilstein J Org Chem. 2017 Nov 6;13:2364-2371. doi: 10.3762/bjoc.13.233. eCollection 2017.
5
A Stereocontrolled Protocol to Highly Functionalized Fluorinated Scaffolds through a Fluoride Opening of Oxiranes.一种通过环氧乙烷的氟化物开环反应制备高官能化氟化骨架的立体控制方法。
Molecules. 2016 Nov 17;21(11):1493. doi: 10.3390/molecules21111493.
6
Chemoselective, Substrate-directed Fluorination of Functionalized Cyclopentane β-Amino Acids.官能化环戊烷β-氨基酸的化学选择性、底物导向氟化反应
Chem Asian J. 2016 Dec 6;11(23):3376-3381. doi: 10.1002/asia.201601046. Epub 2016 Oct 10.
7
Fluorination methods in drug discovery.药物研发中的氟化方法。
Org Biomol Chem. 2016 Sep 28;14(36):8398-427. doi: 10.1039/c6ob00764c. Epub 2016 Aug 10.
8
Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II-III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas.含氟药物的下一代，主要制药公司目前处于II-III期临床试验的化合物：新的结构趋势和治疗领域。
Chem Rev. 2016 Jan 27;116(2):422-518. doi: 10.1021/acs.chemrev.5b00392. Epub 2016 Jan 12.
9
A novel and selective fluoride opening of aziridines by XtalFluor-E. synthesis of fluorinated diamino acid derivatives.通过XtalFluor-E实现的一种新型且选择性的氮丙啶氟化物开环反应：氟化二氨基酸衍生物的合成。
Org Lett. 2015 Mar 6;17(5):1074-7. doi: 10.1021/acs.orglett.5b00182. Epub 2015 Feb 16.
10
Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).制药行业中的氟：过去十年（2001 - 2011年）推向市场的含氟药物
Chem Rev. 2014 Feb 26;114(4):2432-506. doi: 10.1021/cr4002879. Epub 2013 Dec 3.