• 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,-环亚甲胺叶立德与烯丙基烷基酮的 1,3-偶极环加成反应不对称合成四氢异喹啉衍生物。

Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of ,-Cyclic Azomethine Imines with Allyl Alkyl Ketones.

机构信息

School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, China.

School of Pharmacy, Xinxiang University, Xinxiang 453000, China.

出版信息

Molecules. 2021 May 17;26(10):2969. doi: 10.3390/molecules26102969.

DOI:10.3390/molecules26102969
PMID:34067645
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8156229/
Abstract

A [3 + 2] 1,3-Dipolar cycloaddition of ,-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of the product was previously determined by using the quantum electronic circular dichroism calculation and ECD spectrum method.

摘要

[3 + 2] 1,3-偶极环加成反应已应用于 -环状亚甲胺叶立德与烯丙基烷基酮的反应。该反应在温和条件下进行,并能耐受广泛的官能团。一系列四氢异喹啉衍生物通常以良好的非对映选择性和对映选择性(高达>25:1 dr,>95%ee)构建。此外,通过使用量子电子圆二色性计算和 ECD 光谱方法,先前已确定了产物的绝对构型。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b74/8156229/7de7091d5921/molecules-26-02969-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b74/8156229/e44ee90c06c5/molecules-26-02969-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b74/8156229/bd95d6457f10/molecules-26-02969-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b74/8156229/e5a943480381/molecules-26-02969-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b74/8156229/5bf2838b907a/molecules-26-02969-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b74/8156229/7de7091d5921/molecules-26-02969-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b74/8156229/e44ee90c06c5/molecules-26-02969-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b74/8156229/bd95d6457f10/molecules-26-02969-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b74/8156229/e5a943480381/molecules-26-02969-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b74/8156229/5bf2838b907a/molecules-26-02969-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b74/8156229/7de7091d5921/molecules-26-02969-sch002.jpg

相似文献

1
Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of ,-Cyclic Azomethine Imines with Allyl Alkyl Ketones.通过,-环亚甲胺叶立德与烯丙基烷基酮的 1,3-偶极环加成反应不对称合成四氢异喹啉衍生物。
Molecules. 2021 May 17;26(10):2969. doi: 10.3390/molecules26102969.
2
Chiral-Boron-Complex-Catalyzed Asymmetric [3 + 2] Cycloaddition of β-Trifluoromethyl α,β-Unsaturated Ketones with '-Cyclic Azomethine Imines.手性硼配合物催化的β-三氟甲基α,β-不饱和酮与'-环甲亚胺亚胺的不对称[3+2]环加成反应
J Org Chem. 2023 Dec 1;88(23):16566-16580. doi: 10.1021/acs.joc.3c02106. Epub 2023 Nov 15.
3
Chemodivergent 1,3-Dipolar Cycloadditions of ,-Cyclic Azomethine Imines with γ-Sulfonamido-α,β-Unsaturated Ketones to Synthesize Tricyclic Dinitrogen-Fused Heterocycles.γ-环亚甲胺亚胺与γ-磺酰胺基-α,β-不饱和酮的化学发散性1,3-偶极环加成反应合成三环二氮稠合杂环
J Org Chem. 2023 Feb 3;88(3):1772-1785. doi: 10.1021/acs.joc.2c02949. Epub 2023 Jan 24.
4
Organocatalytic asymmetric inverse-electron-demand 1,3-dipolar cycloaddition of N,N'-cyclic azomethine imines.N,N'-环甲亚胺亚胺的有机催化不对称逆电子需求1,3-偶极环加成反应
J Org Chem. 2014 Oct 3;79(19):9305-12. doi: 10.1021/jo5018469. Epub 2014 Sep 17.
5
Enantioselective 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines to unsaturated nitriles catalyzed by NiII-Pigiphos.手性镍(II)-Pigiphos 催化 C,N-环亚胺腙与不饱和腈的对映选择性 1,3-偶极环加成反应。
J Org Chem. 2013 Oct 4;78(19):9638-46. doi: 10.1021/jo401247d. Epub 2013 Sep 16.
6
Nickel(II)-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine imines with alkylidene malonates.镍(II)催化的吖嗪亚胺与亚甲基丙二酸酯的对映选择性 1,3-偶极环加成反应。
Chemistry. 2013 Apr 15;19(16):5134-40. doi: 10.1002/chem.201203891. Epub 2013 Feb 27.
7
Chiral NHC-catalyzed 1,3-dipolar [3 + 2] cycloaddition of azomethine imines with α-chloroaldehydes for the synthesis of bicyclic pyrazolidinones.手性 NHC 催化的吖嗪亚胺与α-氯代醛的 1,3-偶极环加成反应合成双环吡唑烷酮。
Org Biomol Chem. 2018 Jun 20;16(24):4433-4438. doi: 10.1039/c8ob00925b.
8
Asymmetric [3 + 2] Cycloaddition of Methyleneindolinones with N,N'-Cyclic Azomethine Imines Catalyzed by a N,N'-Dioxide-Mg(OTf)2 Complex.N,N'-二氧化物-Mg(OTf)₂络合物催化的亚甲基吲哚酮与N,N'-环甲亚胺亚胺的不对称[3+2]环加成反应
J Org Chem. 2015 Oct 2;80(19):9691-9. doi: 10.1021/acs.joc.5b01760.
9
1,3-Dipolar Cycloaddition between Dehydroalanines and C,N-Cyclic Azomethine Imines: Application to Late-Stage Peptide Modification.去氢丙氨酸与 C,N-环亚甲胺叶立德的 1,3-偶极环加成:在晚期肽修饰中的应用。
Angew Chem Int Ed Engl. 2021 Mar 1;60(10):5331-5338. doi: 10.1002/anie.202012523. Epub 2021 Jan 18.
10
Desymmetrization of 1,4-pentadien-3-ol by the asymmetric 1,3-dipolar cycloaddition of azomethine imines.通过甲亚胺亚胺的不对称1,3-偶极环加成反应实现1,4-戊二烯-3-醇的去对称化
Chemistry. 2014 Feb 10;20(7):2058-64. doi: 10.1002/chem.201302889. Epub 2014 Jan 8.

本文引用的文献

1
Iridium-Catalyzed Asymmetric Hydrogenation of Sterically Hindered Cyclic Imines for Enantioselective Synthesis of Tetrahydroisoquinolines.铱催化的立体位阻环亚胺的不对称氢化反应用于四氢异喹啉的对映选择性合成。
Org Lett. 2021 Jan 1;23(1):140-144. doi: 10.1021/acs.orglett.0c03858. Epub 2020 Dec 22.
2
1,3-Dipolar Cycloaddition between Dehydroalanines and C,N-Cyclic Azomethine Imines: Application to Late-Stage Peptide Modification.去氢丙氨酸与 C,N-环亚甲胺叶立德的 1,3-偶极环加成:在晚期肽修饰中的应用。
Angew Chem Int Ed Engl. 2021 Mar 1;60(10):5331-5338. doi: 10.1002/anie.202012523. Epub 2021 Jan 18.
3
Berberine: A Promising Natural Isoquinoline Alkaloid for the Development of Hypolipidemic Drugs.
小檗碱:一种有前途的天然异喹啉生物碱,可用于开发降血脂药物。
Curr Top Med Chem. 2020;20(28):2634-2647. doi: 10.2174/1568026620666200908165913.
4
Biologically active isoquinoline alkaloids covering 2014-2018.生物活性异喹啉生物碱综述 2014-2018.
Med Res Rev. 2020 Nov;40(6):2212-2289. doi: 10.1002/med.21703. Epub 2020 Jul 29.
5
Cross 1,3-dipolar cycloadditions of C,N-cyclic azomethine imines with an N-benzyl azomethine ylide: facile access to fused tricyclic 1,2,4-hexahydrotriazines.C,N-环亚甲胺叶立德与 N-苄基亚甲胺叶立德的 1,3-偶极环加成反应:易于合成稠合的三环 1,2,4-六氢三嗪。
Org Biomol Chem. 2019 Jan 2;17(2):244-247. doi: 10.1039/c8ob02932f.
6
Silver(I)- and Base-Mediated [3 + 3]-Cycloaddition of C,N-Cyclic Azomethine Imines with Aza-oxyallyl Cations.银(I)和基底介导的 C,N-环亚甲胺亚胺与氮杂氧杂烯阳离子的 [3 + 3]-环加成反应。
Org Lett. 2018 Jan 5;20(1):52-55. doi: 10.1021/acs.orglett.7b03344. Epub 2017 Dec 7.
7
Base-mediated diastereoselective [4 + 3] annulation of in situ generated ortho-quinone methides with C,N-cyclic azomethine imines.碱介导的原位生成的邻醌甲基化物与C,N-环偶氮甲碱亚胺的非对映选择性[4 + 3]环化反应。
Org Biomol Chem. 2017 Sep 20;15(36):7513-7517. doi: 10.1039/c7ob01783a.
8
Chrodrimanins K-N and Related Meroterpenoids from the Fungus Penicillium sp. SCS-KFD09 Isolated from a Marine Worm, Sipunculus nudus.从海洋蠕虫裸体方格星虫中分离出的青霉菌Penicillium sp. SCS-KFD09产生的Chrodrimanins K-N及相关半萜类化合物。
J Nat Prod. 2017 Apr 28;80(4):1039-1047. doi: 10.1021/acs.jnatprod.6b01061. Epub 2017 Feb 17.
9
Asymmetric Synthesis of Isoquinoline Alkaloids: 2004-2015.异喹啉生物碱的不对称合成:2004-2015 年。
Chem Rev. 2016 Oct 12;116(19):12369-12465. doi: 10.1021/acs.chemrev.6b00315. Epub 2016 Sep 29.
10
Catalytic Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Azlactones: Access to Chiral Tricyclic Tetrahydroisoquinolines.C,N-环亚甲胺叶立德与氮杂环丁酮的催化不对称逆电子需求 1,3-偶极环加成反应:手性三环四氢异喹啉的构建。
Angew Chem Int Ed Engl. 2016 Jul 4;55(28):8100-3. doi: 10.1002/anie.201602880. Epub 2016 May 11.