• 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

伯胺的连续流合成：用三氯硅烷对脂肪族和芳香族硝基衍生物进行无金属还原。

Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane.

作者信息

Porta Riccardo, Puglisi Alessandra, Colombo Giacomo, Rossi Sergio, Benaglia Maurizio

机构信息

Dipartimento di Chimica, Università di Milano, Via Golgi 19, 20133, Milano, Italy.

出版信息

Beilstein J Org Chem. 2016 Dec 5;12:2614-2619. doi: 10.3762/bjoc.12.257. eCollection 2016.

DOI:10.3762/bjoc.12.257
PMID:28144331
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5238609/
Abstract

The metal-free reduction of nitro compounds to amines mediated by trichlorosilane was successfully performed for the first time under continuous-flow conditions. Aromatic as well as aliphatic nitro derivatives were converted to the corresponding primary amines in high yields and very short reaction times with no need for purification. The methodology was also extended to the synthesis of two synthetically relevant intermediates (precursors of baclofen and boscalid).

摘要

首次在连续流动条件下成功实现了由三氯硅烷介导的硝基化合物无金属还原为胺的反应。芳香族和脂肪族硝基衍生物在极短的反应时间内以高收率转化为相应的伯胺，无需纯化。该方法还扩展到两种具有合成相关性的中间体（巴氯芬和啶酰菌胺的前体）的合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/2449c920916a/Beilstein_J_Org_Chem-12-2614-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/c5528549aa79/Beilstein_J_Org_Chem-12-2614-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/068e4aca94a8/Beilstein_J_Org_Chem-12-2614-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/efa713410f24/Beilstein_J_Org_Chem-12-2614-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/e3c612570362/Beilstein_J_Org_Chem-12-2614-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/bed0222ce176/Beilstein_J_Org_Chem-12-2614-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/2449c920916a/Beilstein_J_Org_Chem-12-2614-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/c5528549aa79/Beilstein_J_Org_Chem-12-2614-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/068e4aca94a8/Beilstein_J_Org_Chem-12-2614-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/efa713410f24/Beilstein_J_Org_Chem-12-2614-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/e3c612570362/Beilstein_J_Org_Chem-12-2614-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/bed0222ce176/Beilstein_J_Org_Chem-12-2614-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2393/5238609/2449c920916a/Beilstein_J_Org_Chem-12-2614-g007.jpg

相似文献

1
Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane.伯胺的连续流合成：用三氯硅烷对脂肪族和芳香族硝基衍生物进行无金属还原。
Beilstein J Org Chem. 2016 Dec 5;12:2614-2619. doi: 10.3762/bjoc.12.257. eCollection 2016.
2
Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles.无金属脱氮：手性硝基烷烃α-取代的对映体富集腈的简便入口。
Chemistry. 2021 Jul 16;27(40):10247-10250. doi: 10.1002/chem.202100889. Epub 2021 Jun 15.
3
A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin.一种用于在流动体系中合成雷沙吉兰和坦索罗辛高级前体的立体选择性催化策略。
Bioorg Med Chem. 2017 Dec 1;25(23):6242-6247. doi: 10.1016/j.bmc.2017.01.023. Epub 2017 Jan 21.
4
Selective N-alkylation of amines using nitriles under hydrogenation conditions: facile synthesis of secondary and tertiary amines.在加氢条件下使用腈对胺进行选择性 N-烷基化：仲胺和叔胺的简便合成。
Org Biomol Chem. 2012 Jan 14;10(2):293-304. doi: 10.1039/c1ob06303k. Epub 2011 Nov 9.
5
Metal-Free Reduction of Aromatic and Aliphatic Nitro Compounds to Amines: A HSiCl3-Mediated Reaction of Wide General Applicability.无金属还原芳香族和脂肪族硝基化合物为胺：一种具有广泛普遍适用性的 HSiCl3 介导反应。
Org Lett. 2015 Aug 21;17(16):3941-3. doi: 10.1021/acs.orglett.5b01698. Epub 2015 Aug 11.
6
Reductive monoalkylation of aromatic and aliphatic nitro compounds and the corresponding amines with nitriles.芳香族和脂肪族硝基化合物以及相应胺类与腈的还原单烷基化反应。
Org Lett. 2005 Feb 3;7(3):471-4. doi: 10.1021/ol047580f.
7
Mechanochemical Catalytic Transfer Hydrogenation of Aromatic Nitro Derivatives.机械化学催化芳香族硝基衍生物的转移氢化。
Molecules. 2018 Nov 30;23(12):3163. doi: 10.3390/molecules23123163.
8
Electrolytic Conversion of Nitro Compounds into Amines in a Membrane Reactor.膜反应器中硝基化合物的电解转化为胺类
J Am Chem Soc. 2024 Oct 1. doi: 10.1021/jacs.4c07847.
9
Tailored photoenzymatic systems for selective reduction of aliphatic and aromatic nitro compounds fueled by light.光驱动的定制光酶系统用于选择性还原脂肪族和芳香族硝基化合物。
Nat Commun. 2023 Sep 6;14(1):5442. doi: 10.1038/s41467-023-41194-w.
10
Metal-Free Reduction of Aromatic Nitro Compounds to Aromatic Amines with B2pin2 in Isopropanol.无金属条件下 B2pin2 在异丙醇中还原芳香族硝基化合物为芳香族胺。
Org Lett. 2016 Jun 3;18(11):2774-6. doi: 10.1021/acs.orglett.6b01274. Epub 2016 May 23.

引用本文的文献

1
Copper-Catalyzed Continuous-Flow Transfer Hydrogenation of Nitroarenes to Anilines: A Scalable and Reliable Protocol.铜催化硝基芳烃连续流动转移加氢制苯胺：一种可扩展且可靠的方法。
Org Process Res Dev. 2023 Dec 21;28(5):1515-1528. doi: 10.1021/acs.oprd.3c00144. eCollection 2024 May 17.
2
Enantioselective Flow Synthesis of Rolipram Enabled by a Telescoped Asymmetric Conjugate Addition-Oxidative Aldehyde Esterification Sequence Using -Generated Persulfuric Acid as Oxidant.通过缩合不对称共轭加成-氧化醛酯化序列，使用 - 生成过硫酸氢作为氧化剂，实现罗利普兰的对映选择性流合成。
Org Lett. 2022 Feb 4;24(4):1066-1071. doi: 10.1021/acs.orglett.1c04300. Epub 2022 Jan 20.
3

本文引用的文献

1
Flow chemistry as a discovery tool to access sp-sp cross-coupling reactions diazo compounds.流动化学作为一种用于实现sp-sp交叉偶联反应重氮化合物的发现工具。
Chem Sci. 2015 Feb 1;6(2):1120-1125. doi: 10.1039/c4sc03072a. Epub 2014 Nov 7.
2
HSiCl3-Mediated Reduction of Nitro-Derivatives to Amines: Is Tertiary Amine-Stabilized SiCl2 the Actual Reducing Species?
J Org Chem. 2016 Apr 1;81(7):3037-41. doi: 10.1021/acs.joc.6b00191. Epub 2016 Mar 10.
3
Metal-Free Reduction of Aromatic and Aliphatic Nitro Compounds to Amines: A HSiCl3-Mediated Reaction of Wide General Applicability.无金属还原芳香族和脂肪族硝基化合物为胺：一种具有广泛普遍适用性的 HSiCl3 介导反应。
Continuous flow synthesis of lipophilic cations derived from benzoic acid as new cytotoxic chemical entities in human head and neck carcinoma cell lines.
连续流动合成源自苯甲酸的亲脂性阳离子作为人头颈部癌细胞系中的新型细胞毒性化学实体。
RSC Med Chem. 2020 Aug 19;11(10):1210-1225. doi: 10.1039/d0md00153h. eCollection 2020 Oct 1.
4
Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut.连续流合成γ-硝基丁酸光学活性作为关键中间体的巴氯芬，苯并呋喃，和氟苯并呋喃。
Org Lett. 2020 Oct 16;22(20):8122-8126. doi: 10.1021/acs.orglett.0c03100. Epub 2020 Oct 7.
Org Lett. 2015 Aug 21;17(16):3941-3. doi: 10.1021/acs.orglett.5b01698. Epub 2015 Aug 11.
4
The expanding utility of continuous flow hydrogenation.连续流动氢化的应用不断拓展。
Org Biomol Chem. 2015 Jul 14;13(26):7119-30. doi: 10.1039/c5ob01067e. Epub 2015 Jun 15.
5
A Versatile Room-Temperature Route to Di- and Trisubstituted Allenes Using Flow-Generated Diazo Compounds.一种使用流动生成的重氮化合物在室温下合成二取代和三取代烯丙基的通用方法。
Angew Chem Int Ed Engl. 2015 Jun 26;54(27):7920-3. doi: 10.1002/anie.201501538. Epub 2015 May 26.
6
Continuous-flow technology—a tool for the safe manufacturing of active pharmaceutical ingredients.连续流技术——一种用于安全制造活性药物成分的工具。
Angew Chem Int Ed Engl. 2015 Jun 1;54(23):6688-728. doi: 10.1002/anie.201409318. Epub 2015 May 18.
7
Multistep continuous-flow synthesis of (R)- and (S)-rolipram using heterogeneous catalysts.使用多相催化剂的 (R)-和 (S)-罗利普兰的多步连续流合成。
Nature. 2015 Apr 16;520(7547):329-32. doi: 10.1038/nature14343.
8
Immobilization and continuous recycling of photoredox catalysts in ionic liquids for applications in batch reactions and flow systems: catalytic alkene isomerization by using visible light.用于间歇反应和流动体系的离子液体中光氧化还原催化剂的固定化及连续循环利用：利用可见光催化烯烃异构化
Chemistry. 2015 Mar 27;21(14):5350-4. doi: 10.1002/chem.201406653. Epub 2015 Feb 18.
9
The past, present and potential for microfluidic reactor technology in chemical synthesis.微流控反应器技术在化学合成中的过去、现在和未来。
Nat Chem. 2013 Nov;5(11):905-15. doi: 10.1038/nchem.1753. Epub 2013 Oct 13.
10
Heating under high-frequency inductive conditions: application to the continuous synthesis of the neurolepticum olanzapine (Zyprexa).高频感应条件下的加热：应用于抗精神病药物奥氮平（再普乐）的连续合成。
Angew Chem Int Ed Engl. 2013 Sep 9;52(37):9813-7. doi: 10.1002/anie.201302239. Epub 2013 Jul 24.