• 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

获得带有偕二氟甲基和二氟甲基膦酸酯基团的环丙烷。

Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups.

作者信息

Hajdin Ita, Pajkert Romana, Keßler Mira, Han Jianlin, Mei Haibo, Röschenthaler Gerd-Volker

机构信息

School of Science, Constructor University Bremen gGmbH, Campus Ring 1, Bremen 28759, Germany.

Center for Molecular Materials, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany.

出版信息

Beilstein J Org Chem. 2023 Apr 25;19:541-549. doi: 10.3762/bjoc.19.39. eCollection 2023.

DOI:10.3762/bjoc.19.39
PMID:37153646
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10155617/
Abstract

A synthetic route to the bench-stable fluorinated masked carbene reagent diethyl 2-diazo-1,1,3,3,3-pentafluoropropylphosphonate, bearing a trifluoromethyl and a difluoromethyl group is reported for the first time. Its application in CuI-catalyzed cyclopropanation reactions with aromatic and aliphatic terminal alkenes under mild reaction conditions is demonstrated. In total, sixteen new cyclopropanes were synthesized in good to very good yields.

摘要

首次报道了一种合成具有三氟甲基和二氟甲基的、在实验台上稳定的氟化掩蔽卡宾试剂2-重氮基-1,1,3,3,3-五氟丙基膦酸二乙酯的路线。证明了其在温和反应条件下与芳香族和脂肪族末端烯烃进行的CuI催化环丙烷化反应中的应用。总共以良好至非常好的产率合成了16种新的环丙烷。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/8306510566d1/Beilstein_J_Org_Chem-19-541-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/19b36d096e16/Beilstein_J_Org_Chem-19-541-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/abbf7e269f23/Beilstein_J_Org_Chem-19-541-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/93a61ac15057/Beilstein_J_Org_Chem-19-541-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/54b287a1ef05/Beilstein_J_Org_Chem-19-541-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/0a0c8d29797c/Beilstein_J_Org_Chem-19-541-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/475f6f303a76/Beilstein_J_Org_Chem-19-541-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/57cb665b4405/Beilstein_J_Org_Chem-19-541-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/cf9ceb232981/Beilstein_J_Org_Chem-19-541-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/8306510566d1/Beilstein_J_Org_Chem-19-541-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/19b36d096e16/Beilstein_J_Org_Chem-19-541-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/abbf7e269f23/Beilstein_J_Org_Chem-19-541-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/93a61ac15057/Beilstein_J_Org_Chem-19-541-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/54b287a1ef05/Beilstein_J_Org_Chem-19-541-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/0a0c8d29797c/Beilstein_J_Org_Chem-19-541-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/475f6f303a76/Beilstein_J_Org_Chem-19-541-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/57cb665b4405/Beilstein_J_Org_Chem-19-541-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/cf9ceb232981/Beilstein_J_Org_Chem-19-541-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82b7/10155617/8306510566d1/Beilstein_J_Org_Chem-19-541-g010.jpg

相似文献

1
Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups.获得带有偕二氟甲基和二氟甲基膦酸酯基团的环丙烷。
Beilstein J Org Chem. 2023 Apr 25;19:541-549. doi: 10.3762/bjoc.19.39. eCollection 2023.
2
Molybdenum-Catalyzed Deoxygenative Cyclopropanation of 1,2-Dicarbonyl or Monocarbonyl Compounds.钼催化的1,2-二羰基或单羰基化合物的脱氧环丙烷化反应
Angew Chem Int Ed Engl. 2021 Jul 5;60(28):15254-15259. doi: 10.1002/anie.202103429. Epub 2021 Jun 4.
3
Asymmetric Synthesis of Fluoro, Fluoromethyl, Difluoromethyl, and Trifluoromethylcyclopropanes.氟代、氟甲基、二氟甲基和三氟甲基环丙烷的不对称合成。
Acc Chem Res. 2021 Jul 20;54(14):2969-2990. doi: 10.1021/acs.accounts.1c00261. Epub 2021 Jul 7.
4
"Cyclopropanation of Cyclopropanes": GaCl-Mediated Ionic Cyclopropanation of Donor-Acceptor Cyclopropanes with Diazo Esters as a Route to Tetrasubstituted Activated Cyclopropanes.“环丙烷的环丙烷化反应”：以重氮酯为原料，通过GaCl介导的给体-受体环丙烷离子型环丙烷化反应合成四取代活性环丙烷的方法。
J Org Chem. 2021 Mar 19;86(6):4567-4579. doi: 10.1021/acs.joc.0c02983. Epub 2021 Mar 4.
5
General Cyclopropane Assembly by Enantioselective Transfer of a Redox-Active Carbene to Aliphatic Olefins.通过手性氧化-还原卡宾对脂肪族烯烃的对映选择性转移实现丙环的通用合成。
Angew Chem Int Ed Engl. 2019 Apr 23;58(18):5930-5935. doi: 10.1002/anie.201814123. Epub 2019 Feb 15.
6
Rhodium-catalyzed cyclopropanation of fluorinated olefins: a straightforward route to highly functionalized fluorocyclopropanes.铑催化的氟化烯烃环丙烷化反应：通往高官能化氟代环丙烷的直接途径。
Org Lett. 2015 Apr 3;17(7):1790-3. doi: 10.1021/acs.orglett.5b00576. Epub 2015 Mar 13.
7
α-Diazo-β-ketonitriles: uniquely reactive substrates for arene and alkene cyclopropanation.α-重氮-β-酮腈：芳环和烯烃环丙烷化的独特反应性底物。
J Am Chem Soc. 2013 May 15;135(19):7304-11. doi: 10.1021/ja401610p. Epub 2013 May 3.
8
Iron-catalyzed preparation of trifluoromethyl substituted vinyl- and alkynylcyclopropanes.铁催化制备三氟甲基取代的乙烯基和炔基环丙烷。
Org Lett. 2011 Jun 17;13(12):3080-1. doi: 10.1021/ol200983s. Epub 2011 May 17.
9
Asymmetric Rh(II)-catalyzed cyclopropanation of alkenes with diacceptor diazo compounds: p-methoxyphenyl ketone as a general stereoselectivity controlling group.不对称 Rh(II)催化烯烃与双接受体重氮化合物的环丙烷化反应：对甲氧基苯基酮作为通用的立体选择性控制基团。
J Am Chem Soc. 2011 Jun 15;133(23):8972-81. doi: 10.1021/ja201237j. Epub 2011 May 18.
10
Use of Cyclopropane as C1 Synthetic Unit by Directed Retro-Cyclopropanation with Ethylene Release.通过乙烯释放的定向逆环丙烷化反应将环丙烷用作C1合成单元。
J Am Chem Soc. 2018 Nov 14;140(45):15425-15429. doi: 10.1021/jacs.8b09297. Epub 2018 Nov 2.

本文引用的文献

1
Stereoselective Preparation of CF-Containing Cyclopropanes.立体选择性制备含 CF 的环丙烷。
Org Lett. 2022 Dec 16;24(49):9076-9080. doi: 10.1021/acs.orglett.2c03714. Epub 2022 Dec 1.
2
Asymmetric Synthesis of Fluoro, Fluoromethyl, Difluoromethyl, and Trifluoromethylcyclopropanes.氟代、氟甲基、二氟甲基和三氟甲基环丙烷的不对称合成。
Acc Chem Res. 2021 Jul 20;54(14):2969-2990. doi: 10.1021/acs.accounts.1c00261. Epub 2021 Jul 7.
3
In Situ Generation of Unstable Difluoromethylphosphonate-Containing Diazoalkanes and Their Use in [3 + 2] Cycloaddition Reactions with Vinyl Sulfones.
原位生成含不稳定二氟甲基膦酸酯的重氮烷烃及其在与乙烯基砜的[3 + 2]环加成反应中的应用。
Org Lett. 2021 Feb 5;23(3):1130-1134. doi: 10.1021/acs.orglett.1c00150. Epub 2021 Jan 22.
4
Fluorinated Ylides/Carbenes and Related Intermediates from Phosphonium/Sulfonium Salts.磷盐/锍盐衍生的氟代叶立德/卡宾及相关中间体。
Acc Chem Res. 2020 Aug 18;53(8):1498-1510. doi: 10.1021/acs.accounts.0c00244. Epub 2020 Aug 5.
5
Stable group 8 metal porphyrin mono- and bis(dialkylcarbene) complexes: synthesis, characterization, and catalytic activity.稳定的第8族金属卟啉单（二烷基卡宾）和双（二烷基卡宾）配合物：合成、表征及催化活性
Chem Sci. 2019 Dec 31;11(8):2243-2259. doi: 10.1039/c9sc05432d. eCollection 2020 Feb 28.
6
Difluoroacetaldehyde N-Triftosylhydrazone (DFHZ-Tfs) as a Bench-Stable Crystalline Diazo Surrogate for Diazoacetaldehyde and Difluorodiazoethane.二氟乙醛 N-三氟甲磺酸腙（DFHZ-Tfs）作为一种稳定的晶体重氮代试剂，可替代重氮乙醛和二氟重氮乙烷。
Angew Chem Int Ed Engl. 2020 Apr 16;59(16):6473-6481. doi: 10.1002/anie.202000119. Epub 2020 Mar 2.
7
Sofosbuvir, velpatasvir and voxilaprevir: a new triple combination for hepatitis C virus treatment. One pill fits all? Is it the end of the road?索磷布韦、维帕他韦和伏西瑞韦：丙型肝炎病毒治疗的新型三联组合。一药通用？这是终点吗？
Therap Adv Gastroenterol. 2018 Dec 2;11:1756284818812358. doi: 10.1177/1756284818812358. eCollection 2018.
8
VX-659-Tezacaftor-Ivacaftor in Patients with Cystic Fibrosis and One or Two Phe508del Alleles.VX-659-泰泽卡托维伐替卡与依伐卡托维在携带一个或两个 Phe508del 等位基因的囊性纤维化患者中的疗效。
N Engl J Med. 2018 Oct 25;379(17):1599-1611. doi: 10.1056/NEJMoa1807119. Epub 2018 Oct 18.
9
Glecaprevir/pibrentasvir expands reach while reducing cost and duration of hepatitis C virus therapy.格卡瑞韦/哌仑他韦扩大了治疗范围，同时降低了丙型肝炎病毒治疗的成本和时间。
Hepatol Int. 2018 May;12(3):214-222. doi: 10.1007/s12072-018-9873-y. Epub 2018 May 29.
10
Difluoromethylcarbene for iron-catalyzed cyclopropanation.用于铁催化环丙烷化反应的二氟甲基卡宾
Chem Commun (Camb). 2017 Mar 30;53(27):3870-3873. doi: 10.1039/c7cc01636k.