• 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

Takemoto 硫脲催化剂促进的富电子苯酚和靛红的对映选择性有机催化 Friedel-Crafts 反应。

Enantioselective organocatalytic Friedel-Crafts reaction of electron-rich phenols and isatins by Takemoto's thiourea catalyst.

机构信息

Department of Pharmacy, Jilin Medical University, Jilin, 132013, People's Republic of China.

Department of Basic Medicine, Hubei University of Arts and Sciences, Xiangyang, 441053, People's Republic of China.

出版信息

Mol Divers. 2024 Jun;28(3):1733-1742. doi: 10.1007/s11030-023-10678-8. Epub 2023 Jun 30.

DOI:10.1007/s11030-023-10678-8
PMID:37389779
Abstract

Takemoto's catalysts were used to organocatalyze the enantioselective Friedel-Crafts reaction with different electron-rich phenols and substituted isatins. The resulting 3-aryl-3-hydroxyl-2-oxindoles were obtained in good yields (85-96%) with up to 99% ee. The substrate scope was broadened with this methodology compared to reported examples catalyzed by cinchonidine thiourea.

摘要

竹本催化剂被用于有机催化不同富电子苯酚和取代的靛红的对映选择性傅克反应。得到的 3-芳基-3-羟基-2-氧吲哚以高达 99%的对映体过量收率(85-96%)获得。与报道的由辛可宁硫脲催化的例子相比,该方法拓宽了底物范围。

相似文献

1
Enantioselective organocatalytic Friedel-Crafts reaction of electron-rich phenols and isatins by Takemoto's thiourea catalyst.Takemoto 硫脲催化剂促进的富电子苯酚和靛红的对映选择性有机催化 Friedel-Crafts 反应。
Mol Divers. 2024 Jun;28(3):1733-1742. doi: 10.1007/s11030-023-10678-8. Epub 2023 Jun 30.
2
Organocatalytic Enantioselective Michael Reaction of Aminomaleimides with Nitroolefins Catalyzed by Takemoto's Catalyst.Takemoto 催化剂催化的手性有机催化氮杂迈克尔加成反应。
Molecules. 2022 Nov 12;27(22):7787. doi: 10.3390/molecules27227787.
3
Organocatalytic asymmetric Friedel-Crafts reaction of sesamol with isatins: access to biologically relevant 3-aryl-3-hydroxy-2-oxindoles.芝麻酚与异吲哚酮的有机催化不对称傅克反应:通往具有生物学相关性的3-芳基-3-羟基-2-吲哚酮的途径
Chem Asian J. 2014 May;9(5):1305-10. doi: 10.1002/asia.201301546. Epub 2014 Mar 3.
4
Urea-Derivative Catalyzed Enantioselective Hydroxyalkylation of Hydroxyindoles with Isatins.尿素衍生催化剂促进的羟吲哚与色酮的对映选择性羟烷基化反应。
Molecules. 2019 Oct 31;24(21):3944. doi: 10.3390/molecules24213944.
5
Urea derivative organocatalyzed enantioselective Friedel-Crafts alkylation of α-naphthols with isatins.尿素衍生物有机催化的 α-萘酚与靛红的对映选择性 Friedel-Crafts 烷基化反应。
Chirality. 2022 Jul;34(7):977-988. doi: 10.1002/chir.23447. Epub 2022 Apr 12.
6
Organocatalytic asymmetric addition of naphthols and electron-rich phenols to isatin-derived ketimines: highly enantioselective construction of tetrasubstituted stereocenters.有机催化的萘酚和富电子苯酚与色酮衍生的亚胺的不对称加成:高对映选择性构建四取代立体中心。
Angew Chem Int Ed Engl. 2015 May 18;54(21):6320-4. doi: 10.1002/anie.201501273. Epub 2015 Apr 2.
7
Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of naphthols and electron-rich phenols with 2-aryl-3-indol-3-ones.手性磷酸催化萘酚和富电子酚与2-芳基-3-吲哚-3-酮的对映选择性氮杂傅克反应。
Org Biomol Chem. 2023 Jan 18;21(3):489-493. doi: 10.1039/d2ob02179j.
8
Copper-catalyzed enantioselective Friedel-Crafts alkylation of pyrrole with isatins.铜催化的吡咯与靛红的对映选择性 Friedel-Crafts 烷基化反应。
Org Lett. 2014 Jun 20;16(12):3192-5. doi: 10.1021/ol501086q. Epub 2014 Jun 9.
9
Organocatalytic asymmetric decarboxylative cyanomethylation of isatins using L-proline derived bifunctional thiourea.使用L-脯氨酸衍生的双功能硫脲对异吲哚酮进行有机催化不对称脱羧氰甲基化反应。
Org Biomol Chem. 2014 Jun 28;12(24):4186-91. doi: 10.1039/c4ob00271g.
10
Enantioselective construction of 3-hydroxy oxindoles via decarboxylative addition of β-ketoacids to isatins.通过β-酮酸对靛红的脱羧加成反应构建手性 3-羟基氧吲哚。
Org Lett. 2012 Aug 3;14(15):4018-21. doi: 10.1021/ol301855w. Epub 2012 Jul 25.

本文引用的文献

1
Urea derivative organocatalyzed enantioselective Friedel-Crafts alkylation of α-naphthols with isatins.尿素衍生物有机催化的 α-萘酚与靛红的对映选择性 Friedel-Crafts 烷基化反应。
Chirality. 2022 Jul;34(7):977-988. doi: 10.1002/chir.23447. Epub 2022 Apr 12.
2
Urea-Derivative Catalyzed Enantioselective Hydroxyalkylation of Hydroxyindoles with Isatins.尿素衍生催化剂促进的羟吲哚与色酮的对映选择性羟烷基化反应。
Molecules. 2019 Oct 31;24(21):3944. doi: 10.3390/molecules24213944.
3
Hydroxy-Directed Enantioselective Hydroxyalkylation in the Carbocyclic Ring of Indoles.
羟基导向的吲哚碳环的对映选择性羟烷基化反应。
Org Lett. 2017 Apr 7;19(7):1546-1549. doi: 10.1021/acs.orglett.7b00354. Epub 2017 Mar 27.
4
Organocatalytic enamine-activation of cyclopropanes for highly stereoselective formation of cyclobutanes.有机催化烯胺对环丙烷的活化作用用于高对映选择性地形成环丁烷。
J Am Chem Soc. 2015 Feb 4;137(4):1685-91. doi: 10.1021/ja512573q. Epub 2015 Jan 21.
5
Organocatalytic asymmetric Friedel-Crafts reaction of sesamol with isatins: access to biologically relevant 3-aryl-3-hydroxy-2-oxindoles.芝麻酚与异吲哚酮的有机催化不对称傅克反应:通往具有生物学相关性的3-芳基-3-羟基-2-吲哚酮的途径
Chem Asian J. 2014 May;9(5):1305-10. doi: 10.1002/asia.201301546. Epub 2014 Mar 3.
6
Convolutamydine A and synthetic analogues have antinociceptive properties in mice.卷曲霉素 A 和合成类似物在小鼠中具有镇痛作用。
Pharmacol Biochem Behav. 2013 Jan;103(3):431-9. doi: 10.1016/j.pbb.2012.09.023. Epub 2012 Oct 6.
7
Isatins as privileged molecules in design and synthesis of spiro-fused cyclic frameworks.异吲哚酮作为螺稠环骨架设计与合成中的优势分子。
Chem Rev. 2012 Nov 14;112(11):6104-55. doi: 10.1021/cr300135y. Epub 2012 Sep 6.
8
Recent advances in organocatalytic methods for the synthesis of disubstituted 2- and 3-indolinones.有机催化法在合成二取代和三取代 2-和 3-吲哚啉酮中的最新进展。
Chem Soc Rev. 2012 Nov 7;41(21):7247-90. doi: 10.1039/c2cs35100e. Epub 2012 Aug 16.
9
Discovery of XEN907, a spirooxindole blocker of NaV1.7 for the treatment of pain.XEN907 的发现,一种用于治疗疼痛的 NaV1.7 螺环氧化吲哚阻断剂。
Bioorg Med Chem Lett. 2011 Jun 15;21(12):3676-81. doi: 10.1016/j.bmcl.2011.04.088. Epub 2011 Apr 24.
10
Enantioselective synthesis of SM-130686 based on the development of asymmetric Cu(I)F catalysis to access 2-oxindoles containing a tetrasubstituted carbon.基于不对称铜(I)氟催化的发展实现SM-130686的对映选择性合成,以制备含有四取代碳的2-氧化吲哚。
J Am Chem Soc. 2009 May 27;131(20):6946-8. doi: 10.1021/ja901995a.