• 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

非活化氮丙啶环的区域选择性开环。

Regioselectivity in the ring opening of non-activated aziridines.

机构信息

Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.

出版信息

Chem Soc Rev. 2012 Jan 21;41(2):643-65. doi: 10.1039/c1cs15140a. Epub 2011 Sep 6.

DOI:10.1039/c1cs15140a
PMID:21894345
Abstract

In this critical review, the ring opening of non-activated 2-substituted aziridines via intermediate aziridinium salts will be dealt with. Emphasis will be put on the relationship between the observed regioselectivity and inherent structural features such as the nature of the C2 aziridine substituent and the nature of the electrophile and the nucleophile. This overview should allow chemists to gain insight into the factors governing the regioselectivity in aziridinium ring openings (81 references).

摘要

在这篇评论中,将讨论通过中间氮丙啶盐开环非活化的 2-取代氮丙啶。重点将放在观察到的区域选择性与固有结构特征(如 C2 氮丙啶取代基的性质、亲电和亲核试剂的性质)之间的关系上。这篇综述应该可以让化学家深入了解影响氮丙啶环开环区域选择性的因素(81 篇参考文献)。

相似文献

1
Regioselectivity in the ring opening of non-activated aziridines.非活化氮丙啶环的区域选择性开环。
Chem Soc Rev. 2012 Jan 21;41(2):643-65. doi: 10.1039/c1cs15140a. Epub 2011 Sep 6.
2
Intramolecular pi-pi stacking interactions in 2-substituted N,N-dibenzylaziridinium ions and their regioselectivity in nucleophilic ring-opening reactions.2-取代的 N,N-二苄基氮丙啶鎓离子中的分子内 pi-pi 堆积相互作用及其在亲核开环反应中的区域选择性。
J Org Chem. 2010 Feb 5;75(3):885-96. doi: 10.1021/jo902493w.
3
Opposite regiospecific ring opening of 2-(cyanomethyl)aziridines by hydrogen bromide and benzyl bromide: experimental study and theoretical rationalization.2-(氰甲基)氮丙啶与氢溴酸和溴苄的反区域选择性开环:实验研究和理论推理。
J Org Chem. 2010 Jul 2;75(13):4530-41. doi: 10.1021/jo100687q.
4
Asymmetric route to pyridines bearing a highly functionalized 2-alkyl substituent by aziridine ring-opening reactions.通过氮杂环丙烷开环反应合成带有高度官能化2-烷基取代基的吡啶的不对称方法。
J Org Chem. 2007 May 11;72(10):3859-62. doi: 10.1021/jo070364a. Epub 2007 Apr 14.
5
Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: bromide versus hydride.亲核试剂依赖的2-取代N,N-二苄基氮杂环丙烷离子的区域选择性开环反应:溴离子与氢负离子的比较
Chem Commun (Camb). 2009 May 14(18):2508-10. doi: 10.1039/b822763b. Epub 2009 Apr 1.
6
Lewis acid catalyzed S(N)2-type ring opening of N-activated aziridines with electron-rich arenes/heteroarenes.路易斯酸催化 N-活化氮丙啶与富电子芳基/杂芳基的 S(N)2 型环开反应。
J Org Chem. 2013 Jul 19;78(14):7121-30. doi: 10.1021/jo401028j. Epub 2013 Jul 9.
7
One-pot preparation of piperazines by regioselective ring-opening of non-activated arylaziridines.一锅法通过非活化芳基氮丙啶的区域选择性开环制备哌嗪。
Org Biomol Chem. 2012 Mar 14;10(10):1962-5. doi: 10.1039/c2ob07099e. Epub 2012 Jan 30.
8
Regio- and stereospecific ring opening of 1,1-dialkyl-2-(aryloxymethyl)aziridinium salts by bromide.溴对1,1-二烷基-2-(芳氧基甲基)氮杂环丙烷盐的区域和立体特异性开环反应
Chem Commun (Camb). 2006 Apr 14(14):1554-6. doi: 10.1039/b518298k. Epub 2006 Mar 2.
9
Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines.氮丙啶离子的立体选择性和区域选择性分子内傅克反应在 4-取代四氢异喹啉合成中的应用。
Org Lett. 2013 Dec 6;15(23):5912-5. doi: 10.1021/ol4013537. Epub 2013 Nov 18.
10
Possible reason for the unusual regioselectivity in nucleophilic ring opening of trisubstituted aziridines under mildly basic conditions.三取代氮丙啶在弱碱性条件下亲核开环反应中异常区域选择性的可能原因。
J Org Chem. 2014 Jun 6;79(11):5121-33. doi: 10.1021/jo5006685. Epub 2014 May 21.

引用本文的文献

1
Recent Developments in Catalytic Asymmetric Aziridination.催化不对称氮杂环丙烷化反应的最新进展
Top Curr Chem (Cham). 2025 Sep 10;383(4):40. doi: 10.1007/s41061-025-00519-7.
2
Preparation and Regioselective Ring Opening Reactions of Fused Bicyclic N-Aryl Aziridines.稠合双环 N-芳基氮丙啶的制备及区域选择性开环反应
J Org Chem. 2025 Aug 1;90(30):10756-10770. doi: 10.1021/acs.joc.5c01051. Epub 2025 Jul 18.
3
Asymmetric Aziridination of Allylic Carbamates Using Ion-Paired Rhodium Complexes and Extrapolation to C─H Amination of Phenethyl Carbamates.
使用离子对铑配合物对烯丙基氨基甲酸酯进行不对称氮杂环丙烷化反应并外推至苯乙基氨基甲酸酯的C─H胺化反应。
Angew Chem Int Ed Engl. 2025 Jul;64(29):e202507532. doi: 10.1002/anie.202507532. Epub 2025 May 29.
4
Mechanism and Origin of Regioselectivity in the Phosphine-Catalyzed Heine Reaction.膦催化的海涅反应中区域选择性的机理与起源
J Org Chem. 2025 May 16;90(19):6538-6548. doi: 10.1021/acs.joc.5c00416. Epub 2025 May 7.
5
Photocatalytic Nitrene Radical Anion Generation from Sulfonyl Azides for Intermolecular Aziridination of Unactivated Alkenes.由磺酰叠氮化物光催化生成氮烯自由基阴离子用于未活化烯烃的分子间氮杂环丙烷化反应
J Org Chem. 2025 May 16;90(19):6577-6583. doi: 10.1021/acs.joc.5c00595. Epub 2025 May 3.
6
Aziridine Group Transfer via Transient -Aziridinyl Radicals.通过瞬态氮丙啶基自由基进行的氮丙啶基团转移
J Am Chem Soc. 2024 Nov 13;146(45):30796-30801. doi: 10.1021/jacs.4c14169. Epub 2024 Nov 4.
7
Unlocking the C-centered ring-opening of phosphiranium ions for a straightforward entry to functionalized phosphines.开启磷鎓离子的C中心开环反应,以直接合成功能化膦。
Nat Commun. 2024 Oct 3;15(1):8554. doi: 10.1038/s41467-024-53003-z.
8
Regio- and stereoselective access to highly substituted vinylphosphine oxides via metal-free electrophilic phosphonoiodination of alkynes.通过炔烃的无金属亲电膦酰碘化反应实现区域和立体选择性地合成高度取代的乙烯基氧化膦。
Nat Commun. 2024 Jun 25;15(1):5385. doi: 10.1038/s41467-024-49640-z.
9
Base mediated aza-[2 + 1] annulation and regioselective aziridine ring-opening cascade: mild synthesis of functionalized -amino ketones from cyclic -sulfonyl aldimines and -carbonyl sulfonium salts.碱介导的氮杂-[2 + 1]环化反应和区域选择性氮丙啶开环串联反应:由环状磺酰亚胺和羰基锍盐温和合成官能化β-氨基酮
RSC Adv. 2024 May 28;14(24):17178-17183. doi: 10.1039/d4ra02817a. eCollection 2024 May 22.
10
Relevant Developments in the Use of Three-Component Reactions for the Total Synthesis of Natural Products. The last 15 Years.用于天然产物全合成的三组分反应的相关进展。过去15年。
ChemistryOpen. 2024 May;13(5):e202300306. doi: 10.1002/open.202300306. Epub 2024 Apr 22.