• 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CHF-吡唑啉的光化学分解合成CHF取代的3-氮杂双环[3.1.0]己烷。

Synthesis of CHF-substituted 3-azabicyclo[3.1.0]hexanes by photochemical decomposition of CHF-pyrazolines.

作者信息

Zheng Yang, Yu Xinling, Lv Songyang, Mykhailiuk Pavel K, Ma Qiang, Hai Li, Wu Yong

机构信息

Key Laboratory of Drug-Targeting of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University Chengdu 610041 China

Enamine Ltd. Matrosova 23 01103 Kyiv Ukraine

出版信息

RSC Adv. 2018 Jan 29;8(10):5114-5118. doi: 10.1039/c7ra13141k.

DOI:10.1039/c7ra13141k
PMID:35558341
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9092616/
Abstract

A practical synthesis of CHF-substituted 3-azabicyclo[3.1.0]hexanes was developed for the first time. The key step was photochemical decomposition of CHF-substituted pyrazolines. This protocol has the advantages of simple operation, and mild conditions, as well as excellent functional group tolerance, giving the desired products in moderate to excellent yields.

摘要

首次开发了一种实用的合成CHF取代的3-氮杂双环[3.1.0]己烷的方法。关键步骤是CHF取代的吡唑啉的光化学分解。该方法具有操作简单、条件温和以及对官能团耐受性优异的优点，能以中等至优异的产率得到所需产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/b85928dac099/c7ra13141k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/e3606cd1c7b4/c7ra13141k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/0d55707273f4/c7ra13141k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/645ac3834681/c7ra13141k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/fdd021747049/c7ra13141k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/f436ec3f1675/c7ra13141k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/b85928dac099/c7ra13141k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/e3606cd1c7b4/c7ra13141k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/0d55707273f4/c7ra13141k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/645ac3834681/c7ra13141k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/fdd021747049/c7ra13141k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/f436ec3f1675/c7ra13141k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/940c/9092616/b85928dac099/c7ra13141k-s4.jpg

相似文献

1
Synthesis of CHF-substituted 3-azabicyclo[3.1.0]hexanes by photochemical decomposition of CHF-pyrazolines.通过CHF-吡唑啉的光化学分解合成CHF取代的3-氮杂双环[3.1.0]己烷。
RSC Adv. 2018 Jan 29;8(10):5114-5118. doi: 10.1039/c7ra13141k.
2
2-Azabicyclo[2.1.1]hexanes. 2. Substitutent effects on the bromine-mediated rearrangement of 2-azabicyclo[2.2.0]hex-5-enes.2-氮杂双环[2.1.1]己烷。2. 取代基对2-氮杂双环[2.2.0]己-5-烯溴介导重排的影响。
J Org Chem. 2001 Mar 9;66(5):1805-10. doi: 10.1021/jo0015570.
3
Synthesis of CHF-Containing Heterocycles through Oxy-difluoromethylation Using Low-Cost 3D Printed PhotoFlow Reactors.使用低成本3D打印光流反应器通过氧-二氟甲基化合成含CHF的杂环化合物。
Org Lett. 2024 Apr 12;26(14):2877-2882. doi: 10.1021/acs.orglett.3c03997. Epub 2024 Jan 8.
4
Synthesis of 1-Azabicyclo[2.1.1]hexanes via Formal Single Electron Reduction of Azabicyclo[1.1.0]butanes under Photochemical Conditions.在光化学条件下通过氮杂双环[1.1.0]丁烷的形式单电子还原合成1-氮杂双环[2.1.1]己烷。
Angew Chem Int Ed Engl. 2024 Oct 24;63(44):e202410207. doi: 10.1002/anie.202410207. Epub 2024 Sep 20.
5
AlCl-Mediated CHF Transfer and Cyclocondensation of Difluoromethoxy Functionalized -Phenylenediamines to Access N-Substituted Benzimidazoles.氯化铝介导的二氟甲氧基官能化对苯二胺的碳氢键转移及环缩合反应合成N-取代苯并咪唑
Org Lett. 2022 Aug 26;24(33):6142-6147. doi: 10.1021/acs.orglett.2c02231. Epub 2022 Aug 8.
6
5(6)-anti-Substituted-2-azabicyclo[2.1.1]hexanes: a nucleophilic displacement route.5(6)-取代的 2-氮杂双环[2.1.1]己烷：亲核取代路线。
J Org Chem. 2009 Nov 6;74(21):8232-42. doi: 10.1021/jo901725k.
7
Eco-friendly synthesis and antimicrobial activities of some 1-phenyl-3(5-bromothiophen-2-yl)-5-(substituted phenyl)-2-pyrazolines.某些1-苯基-3（5-溴噻吩-2-基）-5-（取代苯基）-2-吡唑啉的绿色合成及其抗菌活性
Org Med Chem Lett. 2012 Jun 11;2(1):20. doi: 10.1186/2191-2858-2-20.
8
Gold-Catalyzed Nitrene Transfer from Benzofuroxans to -Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes.金催化的苯并呋咱向烯丙基酰胺的氮烯转移：3-氮杂双环[3.1.0]己烷的合成。
J Org Chem. 2021 Sep 17;86(18):12964-12972. doi: 10.1021/acs.joc.1c01654. Epub 2021 Sep 2.
9
Cu(II)-Catalyzed Aminocyclization of -Propargyl Hydrazones to Substituted Pyrazolines.铜（II）催化的炔丙基腙向取代吡唑啉的氨基环化反应。
J Org Chem. 2023 Dec 1;88(23):16340-16351. doi: 10.1021/acs.joc.3c01848. Epub 2023 Nov 10.
10
Copper/Chiral Phosphoric-Acid-Catalyzed Intramolecular Reductive Isocyanide-Alkene (1 + 2) Cycloaddition: Enantioselective Construction of 2-Azabicyclo[3.1.0]hexanes.铜/手性磷酸催化的分子内还原异腈-烯烃（1 + 2）环加成反应：对映选择性构建2-氮杂双环[3.1.0]己烷
J Am Chem Soc. 2024 Mar 27;146(12):7956-7962. doi: 10.1021/jacs.4c00989. Epub 2024 Mar 12.

引用本文的文献

1
Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles.基底促进的乙烯基环丙烷甲酰胺的分子内加成反应，用于构建具有受限构象的氮杂[3.1.0]双环。
Molecules. 2023 Apr 25;28(9):3691. doi: 10.3390/molecules28093691.
2
Non-stabilized diazoalkane synthesis the oxidation of free hydrazones by iodosylbenzene and application in MIRC cyclopropanation.非稳定重氮烷的合成——碘苯对游离腙的氧化及其在MIRC环丙烷化反应中的应用
Chem Sci. 2019 Feb 19;10(13):3802-3806. doi: 10.1039/c8sc05558k. eCollection 2019 Apr 7.

本文引用的文献

1
Photochemical Synthesis of 3-Azabicyclo[3.2.0]heptanes: Advanced Building Blocks for Drug Discovery.光化学合成 3-氮杂双环[3.2.0]庚烷：药物发现的高级构建模块。
J Org Chem. 2017 Sep 15;82(18):9627-9636. doi: 10.1021/acs.joc.7b01678. Epub 2017 Aug 25.
2
Synthesis of 3-azabicyclo[3.1.0]hexane derivatives via palladium-catalyzed cyclopropanation of maleimides with N-tosylhydrazones: practical and facile access to CP-866,087.通过钯催化马来酰亚胺与N-甲苯磺酰腙的环丙烷化反应合成3-氮杂双环[3.1.0]己烷衍生物：实用且简便地合成CP-866,087。
Org Biomol Chem. 2017 Feb 1;15(5):1228-1235. doi: 10.1039/c6ob02137a.
3
Difluoromethyl Bioisostere: Examining the "Lipophilic Hydrogen Bond Donor" Concept.
二氟甲基生物等排体：考察“亲脂氢键供体”概念。
J Med Chem. 2017 Jan 26;60(2):797-804. doi: 10.1021/acs.jmedchem.6b01691. Epub 2017 Jan 17.
4
Fluorinated diazoalkanes - a versatile class of reagents for the synthesis of fluorinated compounds.氟化重氮烷——用于合成含氟化合物的一类通用试剂。
Org Biomol Chem. 2016 Dec 7;14(45):10547-10556. doi: 10.1039/c6ob01618a. Epub 2016 Sep 27.
5
Synthesis and evaluation of 6-pyrazoylamido-3N-substituted azabicyclo[3,1,0]hexane derivatives as T-type calcium channel inhibitors for treatment of neuropathic pain.6-吡唑甲酰胺基-3N-取代氮杂双环[3,1,0]己烷衍生物作为治疗神经性疼痛的T型钙通道抑制剂的合成与评价
Bioorg Med Chem. 2016 Nov 1;24(21):5028-5035. doi: 10.1016/j.bmc.2016.06.006. Epub 2016 Jun 4.
6
Design, Synthesis, and Biological Evaluation of Structurally Rigid Analogues of 4-(3-Hydroxyphenyl)piperidine Opioid Receptor Antagonists.设计、合成及结构刚性类似物的生物评价 4-（3-羟基苯基）哌啶类阿片受体拮抗剂。
J Org Chem. 2016 Nov 4;81(21):10383-10391. doi: 10.1021/acs.joc.6b01366. Epub 2016 Aug 2.
7
Development of a Direct Photocatalytic C-H Fluorination for the Preparative Synthesis of Odanacatib.用于奥达卡替布制备合成的直接光催化C-H氟化反应的开发
Org Lett. 2015 Nov 6;17(21):5200-3. doi: 10.1021/acs.orglett.5b02532. Epub 2015 Oct 20.
8
Photoinduced Decarbonylative Rearrangement of Bicyclo[2.2.2]Octenones: Synthesis of the Marasmane Skeleton.双环[2.2.2]辛烯酮的光诱导脱羰基重排反应：马拉斯烷骨架的合成
J Org Chem. 2015 Nov 6;80(21):10979-91. doi: 10.1021/acs.joc.5b02140. Epub 2015 Oct 21.
9
Palladium-Catalyzed Site-Selective Fluorination of Unactivated C(sp(3))-H Bonds.钯催化的未活化 C(sp(3))-H 键的位点选择性氟化反应。
Org Lett. 2015 Aug 7;17(15):3738-41. doi: 10.1021/acs.orglett.5b01710. Epub 2015 Jul 24.
10
Solid-state photochemistry of crystalline pyrazolines: reliable generation and reactivity control of 1,3-biradicals and their potential for the green chemistry synthesis of substituted cyclopropanes.吡唑啉晶体的固态光化学：1,3-双自由基的可靠生成和反应性控制及其在绿色化学合成取代环丙烷中的潜力。
Photochem Photobiol Sci. 2012 Dec;11(12):1929-37. doi: 10.1039/c2pp25263e.