• 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

无催化剂条件下混合脂肪族有机锌试剂、π-亲电试剂和迈克尔受体的形式共轭加成/缩合或曼尼希多组分反应。

Catalyst-Free Formal Conjugate Addition/Aldol or Mannich Multicomponent Reactions of Mixed Aliphatic Organozinc Reagents, π-Electrophiles and Michael Acceptors.

机构信息

Univ Paris Est Créteil, CNRS, ICMPE, UMR 7182, 2 rue Henri Dunant, 94320 Thiais, France.

出版信息

Molecules. 2023 Feb 1;28(3):1401. doi: 10.3390/molecules28031401.

DOI:10.3390/molecules28031401
PMID:36771065
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9919058/
Abstract

Catalyst-free multicomponent reactions of mixed alkylzinc reagents with Michael acceptors and aldehydes, ketones or activated imines are described. Primary, secondary and tertiary alkylzinc reagents, pre-generated in acetonitrile from the corresponding iodoalkanes, were used in the process, leading to the very efficient formation of a variety of β-hydroxycarbonyl compounds. The imines showed more contrasting results, due to the direct addition of the organozinc compound to the C=N bond. Mechanistic assays involving TEMPO account for a polar instead of a radical character of the reaction.

摘要

描述了混合烷基锌试剂与迈克尔受体以及醛、酮或活化亚胺的无催化剂的多组分反应。在该过程中使用了预先在乙腈中从相应的碘代烷烃生成的伯、仲和叔烷基锌试剂，导致各种β-羟基羰基化合物的非常有效的形成。由于有机锌化合物直接加成到 C=N 键，亚胺的结果则更为不同。涉及 TEMPO 的机理测定说明了反应的极性而不是自由基性质。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/954afb5541f9/molecules-28-01401-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/8221d9a3b127/molecules-28-01401-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/2ae022ebfc7a/molecules-28-01401-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/7c718ce4fda2/molecules-28-01401-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/3cc8bd313388/molecules-28-01401-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/ad1bbc26a5eb/molecules-28-01401-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/775abcac0443/molecules-28-01401-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/9966d5adc76b/molecules-28-01401-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/2cfbece617be/molecules-28-01401-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/080aecd32483/molecules-28-01401-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/954afb5541f9/molecules-28-01401-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/8221d9a3b127/molecules-28-01401-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/2ae022ebfc7a/molecules-28-01401-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/7c718ce4fda2/molecules-28-01401-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/3cc8bd313388/molecules-28-01401-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/ad1bbc26a5eb/molecules-28-01401-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/775abcac0443/molecules-28-01401-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/9966d5adc76b/molecules-28-01401-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/2cfbece617be/molecules-28-01401-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/080aecd32483/molecules-28-01401-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0c1/9919058/954afb5541f9/molecules-28-01401-sch009.jpg

相似文献

1
Catalyst-Free Formal Conjugate Addition/Aldol or Mannich Multicomponent Reactions of Mixed Aliphatic Organozinc Reagents, π-Electrophiles and Michael Acceptors.无催化剂条件下混合脂肪族有机锌试剂、π-亲电试剂和迈克尔受体的形式共轭加成/缩合或曼尼希多组分反应。
Molecules. 2023 Feb 1;28(3):1401. doi: 10.3390/molecules28031401.
2
Mixed Aliphatic Organozinc Reagents as Nonstabilized C-Nucleophiles in the Multicomponent Mannich Reaction.混合脂肪族有机锌试剂作为多组分曼尼希反应中的非稳定 C-亲核试剂。
J Org Chem. 2022 Apr 1;87(7):4961-4964. doi: 10.1021/acs.joc.1c02996. Epub 2022 Mar 10.
3
Difluorocarbene as a Building Block for Consecutive Bond-Forming Reactions.二氟卡宾作为连续成键反应的构建单元。
Acc Chem Res. 2018 May 15;51(5):1272-1280. doi: 10.1021/acs.accounts.8b00079. Epub 2018 Apr 17.
4
Cobalt-Catalyzed Reductive Multicomponent Synthesis of β-Hydroxy- and β-Aminocarbonyl Compounds under Mild Conditions.温和条件下钴催化的β-羟基和β-氨基羰基化合物的还原多组分合成
Chemistry. 2017 Jan 5;23(2):402-406. doi: 10.1002/chem.201604251. Epub 2016 Nov 29.
5
CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.CuH 催化的烯烃官能化：从氨氢化反应到羰基加成反应。
Acc Chem Res. 2020 Jun 16;53(6):1229-1243. doi: 10.1021/acs.accounts.0c00164. Epub 2020 May 13.
6
Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.烯酮、丙烯酸盐和乙烯基杂芳烃给电子体的催化还原Aldol 和 Mannich 反应。
Chem Rev. 2020 Apr 22;120(8):3721-3748. doi: 10.1021/acs.chemrev.0c00053. Epub 2020 Mar 19.
7
Radical-polar crossover domino reactions involving organozinc and mixed organocopper/organozinc reagents.涉及有机锌以及混合有机铜/有机锌试剂的自由基-极性交叉多米诺反应。
Chemistry. 2006 Aug 25;12(25):6506-13. doi: 10.1002/chem.200600334.
8
Catalytic asymmetric organozinc additions to carbonyl compounds.催化不对称有机锌试剂对羰基化合物的加成反应。
Chem Rev. 2001 Mar;101(3):757-824. doi: 10.1021/cr000411y.
9
Asymmetric functional organozinc additions to aldehydes catalyzed by 1,1'-bi-2-naphthols (BINOLs).由1,1'-联-2-萘酚（BINOLs）催化的醛的不对称官能团有机锌加成反应。
Acc Chem Res. 2014 May 20;47(5):1523-35. doi: 10.1021/ar500020k. Epub 2014 Apr 16.
10
α-(Aminomethyl)acrylates as acceptors in radical-polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping.α-（氨甲基）丙烯酸酯在二烷基锌的自由基-极性交叉1,4-加成反应中作为受体：对烯醇盐形成和捕获的见解
Beilstein J Org Chem. 2023 Sep 21;19:1443-1451. doi: 10.3762/bjoc.19.103. eCollection 2023.

本文引用的文献

1
Mixed Aliphatic Organozinc Reagents as Nonstabilized C-Nucleophiles in the Multicomponent Mannich Reaction.混合脂肪族有机锌试剂作为多组分曼尼希反应中的非稳定 C-亲核试剂。
J Org Chem. 2022 Apr 1;87(7):4961-4964. doi: 10.1021/acs.joc.1c02996. Epub 2022 Mar 10.
2
Uncatalyzed conjugate addition of organozinc halides to enones in DME: a combined experimental/computational study on the role of the solvent and the reaction mechanism.二甲基醚中有机卤化锌与烯酮的无催化共轭加成反应：关于溶剂作用和反应机理的实验与计算相结合的研究
Chem Sci. 2019 Nov 11;11(1):257-263. doi: 10.1039/c9sc04820k.
3
Enantioselective Copper-Catalyzed Cyanation of Remote C(sp)-H Bonds Enabled by 1,5-Hydrogen Atom Transfer.
通过1,5-氢原子转移实现的远程C(sp)-H键的对映选择性铜催化氰化反应
iScience. 2019 Nov 22;21:490-498. doi: 10.1016/j.isci.2019.10.048. Epub 2019 Oct 26.
4
Co(I)-Catalyzed [3 + 2] Annulation of o-Haloaryl Imines with Alkenes for the Synthesis of Indanamines.钴（I）催化邻卤代芳基亚胺与烯烃的[3 + 2]环加成反应合成茚满胺。
J Org Chem. 2018 Apr 6;83(7):4078-4086. doi: 10.1021/acs.joc.8b00551. Epub 2018 Mar 26.
5
Cobalt-Catalyzed Reductive Multicomponent Synthesis of β-Hydroxy- and β-Aminocarbonyl Compounds under Mild Conditions.温和条件下钴催化的β-羟基和β-氨基羰基化合物的还原多组分合成
Chemistry. 2017 Jan 5;23(2):402-406. doi: 10.1002/chem.201604251. Epub 2016 Nov 29.
6
Advances in tandem reactions with organozinc reagents.有机锌试剂的串联反应进展。
Chem Soc Rev. 2015 Apr 21;44(8):2489-507. doi: 10.1039/c4cs00430b.
7
Traceless stereoinduction for the enantiopure synthesis of substituted-2-cyclopentenones.无痕迹立体诱导用于取代-2-环戊烯酮的对映纯合成。
Org Lett. 2015 Jan 2;17(1):94-7. doi: 10.1021/ol5032975. Epub 2014 Dec 12.
8
Asymmetric conjugate addition of Grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes.格氏试剂对3-硅基不饱和酯的不对称共轭加成反应，用于简便制备对映体富集的β-硅基羰基化合物和烯丙基硅烷。
Chemistry. 2014 Dec 8;20(50):16764-72. doi: 10.1002/chem.201403849. Epub 2014 Oct 16.
9
A multicomponent approach to the synthesis of N-sulfonyl β(2,3)-amino esters.一种合成N-磺酰基β(2,3)-氨基酯的多组分方法。
Org Biomol Chem. 2014 Jun 7;12(21):3423-6. doi: 10.1039/c3ob42353k. Epub 2014 Apr 17.
10
Copper(I)-catalyzed asymmetric desymmetrization: synthesis of five-membered-ring compounds containing all-carbon quaternary stereocenters.铜（I）催化的不对称去对称化：含全碳季碳立体中心的五元环化合物的合成。
J Am Chem Soc. 2012 Jun 27;134(25):10329-32. doi: 10.1021/ja3032345. Epub 2012 Jun 13.