• 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

2,5-二甲基苯甲酰甲酯:一种用于磷酸盐和磺酸的光可去除保护基团。

2,5-dimethylphenacyl esters: a photoremovable protecting group for phosphates and sulfonic acids.

作者信息

Klán Petr, Pelliccioli Anna Paola, Pospísil Tomás, Wirz Jakob

机构信息

Department of Organic Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, CZ-611 37 Brno, Czech Republic.

出版信息

Photochem Photobiol Sci. 2002 Nov;1(11):920-3. doi: 10.1039/b208171g.

DOI:10.1039/b208171g
PMID:12659533
Abstract

2,5-Dimethylphenacyl phosphoric and sulfonic esters release the corresponding acids upon irradiation in nearly quantitative isolated yields, with quantum yields phi = 0.71 and 0.68 in methanol, 0.09 and 0.19 in benzene. In methanol solution the reactions proceed predominantly via the (Z)-photoenol, the lifetimes of which (20 and 25 micros) were determined by laser flash photolysis. The chromophore is proposed as an excellent photoremovable protecting group for use in organic synthesis and biochemistry.

摘要

2,5-二甲基苯甲酰磷酸酯和磺酸酯在光照下会释放出相应的酸,分离产率接近定量,在甲醇中的量子产率分别为0.71和0.68,在苯中的量子产率分别为0.09和0.19。在甲醇溶液中,反应主要通过(Z)-光烯醇进行,其寿命(20和25微秒)通过激光闪光光解测定。发色团被认为是用于有机合成和生物化学的优秀光可去除保护基团。

相似文献

1
2,5-dimethylphenacyl esters: a photoremovable protecting group for phosphates and sulfonic acids.2,5-二甲基苯甲酰甲酯:一种用于磷酸盐和磺酸的光可去除保护基团。
Photochem Photobiol Sci. 2002 Nov;1(11):920-3. doi: 10.1039/b208171g.
2
2,5-Dimethylphenacyl carbonates: a photoremovable protecting group for alcohols and phenols.2,5-二甲基苯甲酰碳酸酯:一种用于醇类和酚类的光可去除保护基团。
Photochem Photobiol Sci. 2005 Jan;4(1):43-6. doi: 10.1039/b408851d. Epub 2004 Sep 20.
3
Temperature dependent photochemical cleavage of 2,5-dimethylphenacyl esters.2,5-二甲基苯甲酰酯的温度依赖性光化学裂解
Mol Divers. 2003;7(2-4):265-71. doi: 10.1023/b:modi.0000006862.98763.dd.
4
2,5-Dimethylphenacyl carbamate: a photoremovable protecting group for amines and amino acids.2,5-二甲基苯甲酰氨基甲酸酯:一种用于胺类和氨基酸的光可去除保护基团。
Photochem Photobiol Sci. 2007 Jan;6(1):50-6. doi: 10.1039/b612233g. Epub 2006 Nov 6.
5
2-Hydroxyphenacyl ester: a new photoremovable protecting group.2-羟基苯甲酰酯:一种新型光脱保护基。
Photochem Photobiol Sci. 2012 Sep;11(9):1465-75. doi: 10.1039/c2pp25133g. Epub 2012 Jul 6.
6
2,5-Dimethylphenacyl as a new photoreleasable protecting group for carboxylic acids.
Org Lett. 2000 Jun 1;2(11):1569-71. doi: 10.1021/ol005789x.
7
From α-nucleophiles to functionalized aggregates: exploring the reactivity of hydroxamate ion towards esterolytic reactions in micelles.从α-亲核试剂到功能化聚集体:探索异羟肟酸根离子在胶束中对酯解反应的反应活性。
Org Biomol Chem. 2015 Mar 14;13(10):2827-48. doi: 10.1039/c4ob02067g.
8
Photochemical degradation of sunscreen agent 2-phenylbenzimidazole-5-sulfonic acid in different water matrices.不同水基质中防晒剂 2-苯并咪唑-5-磺酸的光化学降解。
Water Res. 2013 Oct 1;47(15):5865-75. doi: 10.1016/j.watres.2013.07.009. Epub 2013 Jul 16.
9
New photoremovable protecting groups for carboxylic acids with high photolytic efficiencies at near-UV irradiation. Application to the photocontrolled release of L-glutamate.用于羧酸的新型光可去除保护基团,在近紫外光照射下具有高光解效率。应用于L-谷氨酸的光控释放。
Chembiochem. 2006 Nov;7(11):1690-5. doi: 10.1002/cbic.200600111.
10
Synthesis and reaction mechanism of a photoremovable protecting group based on 1,4-naphthoquinone.基于1,4-萘醌的光可去除保护基的合成与反应机理
Photochem Photobiol Sci. 2007 Aug;6(8):865-72. doi: 10.1039/b706318k. Epub 2007 Jun 19.

引用本文的文献

1
Sustainable Approaches for the Protection and Deprotection of Functional Groups.官能团保护与脱保护的可持续方法。
Chemistry. 2025 Jul 17;31(40):e202501387. doi: 10.1002/chem.202501387. Epub 2025 Jun 27.
2
Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.可见-近红外光激活释放:从小分子到纳米材料。
Chem Rev. 2020 Dec 23;120(24):13135-13272. doi: 10.1021/acs.chemrev.0c00663. Epub 2020 Oct 30.
3
Photorelease of phosphates: Mild methods for protecting phosphate derivatives.磷酸酯的光解:保护磷酸酯衍生物的温和方法。
Beilstein J Org Chem. 2014 Aug 29;10:2038-54. doi: 10.3762/bjoc.10.212. eCollection 2014.
4
Chemical synthesis of the 5-taurinomethyl(-2-thio)uridine modified anticodon arm of the human mitochondrial tRNA(Leu(UUR)) and tRNA(Lys).人线粒体 tRNA(Leu(UUR))和 tRNA(Lys)的反密码子臂的 5-牛磺酸甲基(-2-硫代)尿苷的化学合成。
RNA. 2014 Jun;20(6):938-47. doi: 10.1261/rna.044412.114. Epub 2014 Apr 22.
5
Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy.化学与生物学中的光可去除保护基团:反应机理与效能
Chem Rev. 2013 Jan 9;113(1):119-91. doi: 10.1021/cr300177k. Epub 2012 Dec 21.
6
Gas-phase fragmentation of deprotonated p-hydroxyphenacyl derivatives.去质子化对羟基苯乙酮衍生物的气相碎裂。
J Org Chem. 2011 Apr 1;76(7):2180-6. doi: 10.1021/jo1025223. Epub 2011 Mar 8.
7
The power of solvent in altering the course of photorearrangements.溶剂在改变光重排反应进程中的作用。
Org Lett. 2011 Feb 18;13(4):644-7. doi: 10.1021/ol102887f. Epub 2011 Jan 14.
8
Temperature dependent photochemical cleavage of 2,5-dimethylphenacyl esters.2,5-二甲基苯甲酰酯的温度依赖性光化学裂解
Mol Divers. 2003;7(2-4):265-71. doi: 10.1023/b:modi.0000006862.98763.dd.