• 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

使用硼氢化钠和氯化铜(II)将β-硝基苯乙烯轻松一锅法还原为苯乙胺。

Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride.

作者信息

D'Andrea Laura, Jademyr Simon

机构信息

Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 København Ø, Denmark.

current address: Department of Chemistry and Bioscience, Aalborg University, Fredrik Bajers Vej 7H, 9220 Aalborg, Denmark.

出版信息

Beilstein J Org Chem. 2025 Jan 7;21:39-46. doi: 10.3762/bjoc.21.4. eCollection 2025.

DOI:10.3762/bjoc.21.4
PMID:39811686
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11729678/
Abstract

Phenethylamines and phenylisopropylamines of scientific relevance can be prepared with a NaBH/CuCl system in 10 to 30 minutes via reduction of substituted β-nitrostyrenes. This one-pot procedure allows the quick isolation of substituted β-nitrostyrene scaffolds with 62-83% yield under mild conditions, without the need for special precautions, inert atmosphere, and time-consuming purification techniques.

摘要

具有科学相关性的苯乙胺和苯异丙胺可通过NaBH/CuCl体系,在10至30分钟内通过还原取代的β-硝基苯乙烯来制备。这种一锅法可在温和条件下快速分离出取代的β-硝基苯乙烯支架,产率为62-83%,无需特殊防护措施、惰性气氛和耗时的纯化技术。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/d49627fda904/Beilstein_J_Org_Chem-21-39-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/ed6f2061f53c/Beilstein_J_Org_Chem-21-39-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/b254cff87f15/Beilstein_J_Org_Chem-21-39-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/b7815e29d955/Beilstein_J_Org_Chem-21-39-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/c50b6d1d54a3/Beilstein_J_Org_Chem-21-39-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/d111322efd80/Beilstein_J_Org_Chem-21-39-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/d49627fda904/Beilstein_J_Org_Chem-21-39-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/ed6f2061f53c/Beilstein_J_Org_Chem-21-39-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/b254cff87f15/Beilstein_J_Org_Chem-21-39-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/b7815e29d955/Beilstein_J_Org_Chem-21-39-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/c50b6d1d54a3/Beilstein_J_Org_Chem-21-39-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/d111322efd80/Beilstein_J_Org_Chem-21-39-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d947/11729678/d49627fda904/Beilstein_J_Org_Chem-21-39-g007.jpg

相似文献

1
Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride.使用硼氢化钠和氯化铜(II)将β-硝基苯乙烯轻松一锅法还原为苯乙胺。
Beilstein J Org Chem. 2025 Jan 7;21:39-46. doi: 10.3762/bjoc.21.4. eCollection 2025.
2
Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors.致幻性苯乙胺和苯异丙胺衍生物对人5-羟色胺(5-HT)2A和5-HT2C受体的功能选择性。
J Pharmacol Exp Ther. 2007 Jun;321(3):1054-61. doi: 10.1124/jpet.106.117507. Epub 2007 Mar 2.
3
Base-promoted multicomponent synthesis of 1,2,4-triazole-based hybrids from 1,3-diones, β-nitrostyrenes, and hydrazones.基于碱促进的1,3 - 二酮、β-硝基苯乙烯和腙合成1,2,4 - 三唑基杂化物的多组分反应
Chem Commun (Camb). 2024 Oct 10;60(82):11718-11721. doi: 10.1039/d4cc03709j.
4
A one-pot synthesis of 7-phenylindolo[3,2-a]carbazoles from indoles and β-nitrostyrenes, via an unprecedented reaction sequence.一锅法从吲哚和β-硝基苯乙烯合成 7-苯基吲哚并[3,2-a]咔唑,通过前所未有的反应序列。
Org Biomol Chem. 2011 Oct 26;9(22):7780-90. doi: 10.1039/c1ob06108a. Epub 2011 Oct 5.
5
Sodium borohydride-nickel chloride hexahydrate in EtOH/PEG-400 as an efficient and recyclable catalytic system for the reduction of alkenes.乙醇/聚乙二醇-400中的硼氢化钠-六水合氯化镍作为一种用于还原烯烃的高效且可循环使用的催化体系。
RSC Adv. 2018 Feb 19;8(14):7761-7764. doi: 10.1039/c8ra00905h. eCollection 2018 Feb 14.
6
The three-component reaction of dicarbomethoxycarbene, aldehydes, and beta-nitrostyrenes: a stereoselective synthesis of substituted tetrahydrofurans.二羰基甲氧基卡宾、醛和β-硝基苯乙烯的三组分反应:取代四氢呋喃的立体选择性合成
J Org Chem. 2004 Feb 20;69(4):1413-4. doi: 10.1021/jo035673p.
7
Copper Nanoparticles Supported on ZIF-8: Comparison of Cu(II) Reduction Processes and Application as Benzyl Alcohol Oxidation Catalysts.负载于ZIF-8上的铜纳米颗粒:Cu(II)还原过程的比较及作为苯甲醇氧化催化剂的应用
ACS Appl Mater Interfaces. 2023 Aug 16;15(32):38716-38728. doi: 10.1021/acsami.3c08906. Epub 2023 Jul 31.
8
Convenient one-pot access to 2H-3-nitrothiochromenes from 2-bromobenzaldehydes, sodium sulfide and β-nitrostyrenes.方便的一锅法从 2-溴苯甲醛、硫化钠和β-硝基苯乙烯制备 2H-3-硝基噻吩。
Org Biomol Chem. 2019 Jul 14;17(26):6355-6358. doi: 10.1039/c9ob01060b. Epub 2019 Jun 19.
9
Effect of precursor type on the reduction of concentrated nitrate using zero-valent copper and sodium borohydride.前驱体类型对使用零价铜和硼氢化钠还原浓缩硝酸盐的影响。
Water Sci Technol. 2018 Jan;77(1-2):114-122. doi: 10.2166/wst.2017.525.
10
Subhallucinogenic Concentrations of Substituted Phenethylamines as a Novel Therapeutic Approach for Inflammatory and Neurological Disorders.取代苯乙胺的亚幻觉浓度作为炎症和神经疾病的一种新型治疗方法。
ACS Med Chem Lett. 2023 Jun 9;14(7):884-885. doi: 10.1021/acsmedchemlett.3c00220. eCollection 2023 Jul 13.

引用本文的文献

1
Copper catalysis: a constantly evolving field.铜催化:一个不断发展的领域。
Beilstein J Org Chem. 2025 Jul 17;21:1477-1479. doi: 10.3762/bjoc.21.109. eCollection 2025.

本文引用的文献

1
MDMA-assisted therapy for moderate to severe PTSD: a randomized, placebo-controlled phase 3 trial.MDMA 辅助治疗中重度 PTSD:一项随机、安慰剂对照的 3 期试验。
Nat Med. 2023 Oct;29(10):2473-2480. doi: 10.1038/s41591-023-02565-4. Epub 2023 Sep 14.
2
Unraveling the In Vitro Toxicity Profile of Psychedelic 2C Phenethylamines and Their -Benzylphenethylamine (NBOMe) Analogues.解析致幻2C苯乙胺及其N-苄基苯乙胺(NBOMe)类似物的体外毒性特征。
Pharmaceuticals (Basel). 2023 Aug 15;16(8):1158. doi: 10.3390/ph16081158.
3
Pharmacology of -(-)-Methamphetamine in Humans: A Systematic Review of the Literature.
(-)-甲基苯丙胺在人体中的药理学:文献系统综述
ACS Pharmacol Transl Sci. 2023 Jun 13;6(7):914-924. doi: 10.1021/acsptsci.3c00019. eCollection 2023 Jul 14.
4
Spirofused Tetrahydroisoquinoline-Oxindole Hybrids (Spiroquindolones) as Potential Multitarget Antimalarial Agents: Preliminary Hit Optimization and Efficacy Evaluation in Mice.螺环稠合四氢异喹啉-氧吲哚杂合体(螺环喹诺酮)作为潜在的多靶抗疟药物:初步命中优化和在小鼠中的疗效评价。
Antimicrob Agents Chemother. 2022 Dec 20;66(12):e0060722. doi: 10.1128/aac.00607-22. Epub 2022 Nov 21.
5
Effects of 5-HT2A receptor agonist 2,5-dimethoxy-4-iodoamphetamine on alcohol consumption in Long-Evans rats.5-HT2A 受体激动剂 2,5-二甲氧基-4-碘苯丙胺对长爪沙鼠饮酒量的影响。
Behav Pharmacol. 2021 Aug 1;32(5):382-391. doi: 10.1097/FBP.0000000000000628.
6
Organic synthesis of high added value molecules with MOF catalysts.使用金属有机框架催化剂进行高附加值分子的有机合成。
Org Biomol Chem. 2020 Oct 21;18(40):8058-8073. doi: 10.1039/d0ob01571g.
7
Synthesis and determination of analytical characteristics and differentiation of positional isomers in the series of N-(2-methoxybenzyl)-2-(dimethoxyphenyl)ethanamine using chromatography-mass spectrometry.采用色谱-质谱法合成并测定 N-(2-甲氧基苄基)-2-(二甲氧基苯基)乙胺系列中位置异构体的分析特性和区分。
Drug Test Anal. 2020 Aug;12(8):1154-1170. doi: 10.1002/dta.2859. Epub 2020 Jun 10.
8
Synthesis and characterization of NiFeO@Cu nanoparticles as a magnetically recoverable catalyst for reduction of nitroarenes to arylamines with NaBH.镍铁氧体@铜纳米粒子的合成与表征及其作为磁性可回收催化剂用于硼氢化钠还原硝基芳烃制芳胺
J Colloid Interface Sci. 2017 Aug 15;500:285-293. doi: 10.1016/j.jcis.2017.03.030. Epub 2017 Mar 7.
9
Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists.作为5-HT2A/2C激动剂的N-苄基苯乙胺的合成及其构效关系
ACS Chem Neurosci. 2014 Mar 19;5(3):243-9. doi: 10.1021/cn400216u. Epub 2014 Jan 15.
10
Characterization of route specific impurities found in methamphetamine synthesized by the Leuckart and reductive amination methods.对通过莱卡特法和还原胺化法合成的甲基苯丙胺中发现的特定路线杂质的表征。
Anal Chem. 2009 Sep 1;81(17):7342-8. doi: 10.1021/ac9005588.