• 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

乙烯基类似物的卡泰拉尼反应：一项计算与实验相结合的研究。

The vinylogous Catellani reaction: a combined computational and experimental study.

作者信息

Yamamoto Y, Murayama T, Jiang J, Yasui T, Shibuya M

机构信息

Department of Basic Medicinal Sciences , Graduate School of Pharmaceutical Sciences , Nagoya University , Chikusa , Nagoya 464-8601 , Japan . Email:

出版信息

Chem Sci. 2017 Nov 30;9(5):1191-1199. doi: 10.1039/c7sc04265e. eCollection 2018 Feb 7.

DOI:10.1039/c7sc04265e
PMID:29675164
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5885779/
Abstract

In the presence of 5 mol% Pd(OAc), 1 equiv. of norbornene, and KCO, the reaction of 4-iodo-2-quinolones with tertiary -bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving vinylic C-H cleavage is proposed based on the results of control experiments and density functional theory calculations.

摘要

在5 mol%醋酸钯、1当量降冰片烯和碳酸钾存在下，4-碘-2-喹诺酮与叔溴代苄醇反应，以中等至高产率生成所需的苯并吡喃稠合2-喹诺酮。基于对照实验结果和密度泛函理论计算，提出了一种涉及乙烯基C-H裂解的卡泰拉尼型机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/5170554983b4/c7sc04265e-s12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/55dafc89d40d/c7sc04265e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/a23bc51cc239/c7sc04265e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/b2869e899a91/c7sc04265e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/a5052cd8ea3a/c7sc04265e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/df25f3ab3faa/c7sc04265e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/2a2f5b1522f0/c7sc04265e-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/001992121311/c7sc04265e-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/f5b53c4b4bcb/c7sc04265e-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/457bff4895ab/c7sc04265e-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/7ed35fd1be76/c7sc04265e-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/07702557f25d/c7sc04265e-s10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/49e4c2f0f6fb/c7sc04265e-s11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/812723e42390/c7sc04265e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/5170554983b4/c7sc04265e-s12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/55dafc89d40d/c7sc04265e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/a23bc51cc239/c7sc04265e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/b2869e899a91/c7sc04265e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/a5052cd8ea3a/c7sc04265e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/df25f3ab3faa/c7sc04265e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/2a2f5b1522f0/c7sc04265e-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/001992121311/c7sc04265e-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/f5b53c4b4bcb/c7sc04265e-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/457bff4895ab/c7sc04265e-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/7ed35fd1be76/c7sc04265e-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/07702557f25d/c7sc04265e-s10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/49e4c2f0f6fb/c7sc04265e-s11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/812723e42390/c7sc04265e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e97/5885779/5170554983b4/c7sc04265e-s12.jpg

相似文献

1
The vinylogous Catellani reaction: a combined computational and experimental study.乙烯基类似物的卡泰拉尼反应：一项计算与实验相结合的研究。
Chem Sci. 2017 Nov 30;9(5):1191-1199. doi: 10.1039/c7sc04265e. eCollection 2018 Feb 7.
2
Palladium(II)-Initiated Catellani-Type Reactions.钯（II）引发的卡塔兰尼型反应。
Angew Chem Int Ed Engl. 2019 Apr 23;58(18):5832-5844. doi: 10.1002/anie.201813491. Epub 2019 Feb 20.
3
The Discovery of a Palladium(II)-Initiated Borono-Catellani Reaction.钯（II）引发的硼代卡斯特拉尼反应的发现。
Angew Chem Int Ed Engl. 2018 Jun 11;57(24):7161-7165. doi: 10.1002/anie.201803865. Epub 2018 May 16.
4
Palladium-Catalyzed [3+2] and [2+2+2] Annulations of 4-Iodo-2-quinolones with Activated Alkynes through Selective C-H Activation.钯催化的通过选择性 C-H 活化的 4-碘-2-喹诺酮与活化炔烃的[3+2]和[2+2+2]环加成反应。
Chemistry. 2020 Mar 23;26(17):3749-3757. doi: 10.1002/chem.201904558. Epub 2020 Feb 7.
5
Mechanism of Pd-catalyzed acylation/alkenylation of aryl iodide: a DFT study.钯催化芳基碘化物的酰化/烯基化反应机理：一项密度泛函理论研究
Org Biomol Chem. 2017 Jul 26;15(29):6147-6156. doi: 10.1039/c7ob01021d.
6
Palladium-catalyzed carbonylative annulation of internal alkynes: synthesis of 3,4-disubstituted coumarins.钯催化内炔的羰基化环化反应：3,4-二取代香豆素的合成
J Org Chem. 2003 Nov 28;68(24):9423-32. doi: 10.1021/jo0350763.
7
Palladium-catalysed norbornene-mediated C-H functionalization of arenes.钯催化的降冰片烯介导的芳烃 C-H 功能化。
Nat Chem. 2015 Nov;7(11):863-70. doi: 10.1038/nchem.2372.
8
Pd/Norbornene: A Winning Combination for Selective Aromatic Functionalization via C-H Bond Activation.钯/降冰片烯：通过 C-H 键活化实现选择性芳基功能化的理想组合。
Acc Chem Res. 2016 Jul 19;49(7):1389-400. doi: 10.1021/acs.accounts.6b00165. Epub 2016 Jun 22.
9
Efficient palladium-catalyzed homocoupling reaction and Sonogashira cross-coupling reaction of terminal alkynes under aerobic conditions.有氧条件下末端炔烃的高效钯催化自偶联反应和Sonogashira交叉偶联反应。
J Org Chem. 2005 May 27;70(11):4393-6. doi: 10.1021/jo0503310.
10
Synthesis, structures, and norbornene polymerization behavior of C(sp³), N-chelated palladacycles bearing o-aryloxide-N-heterocyclic carbene ligands.含邻芳氧基-N-杂环卡宾配体的C(sp³)，N-螯合钯环化合物的合成、结构及降冰片烯聚合行为
Dalton Trans. 2014 Dec 7;43(45):17177-83. doi: 10.1039/c4dt02198c.

引用本文的文献

1
Regioselective C3-C4 difunctionalization of 4-bromocoumarins Pd/norbornene catalysis.4-溴香豆素的区域选择性C3-C4双官能团化：钯/降冰片烯催化
RSC Adv. 2025 Sep 22;15(41):34434-34438. doi: 10.1039/d5ra05007c. eCollection 2025 Sep 17.
2
Stereoselective assembly of C-oligosaccharides via modular difunctionalization of glycals.通过糖烯的模块化双官能化实现C-寡糖的立体选择性组装。
Nat Commun. 2024 Mar 30;15(1):2794. doi: 10.1038/s41467-024-47060-7.
3
Rh(iii)-catalyzed highly site- and regio-selective alkenyl C-H activation/annulation of 4-amino-2-quinolones with alkynes reversible alkyne insertion.

本文引用的文献

1
Computational Studies of Carboxylate-Assisted C-H Activation and Functionalization at Group 8-10 Transition Metal Centers.第八族到第十族过渡金属中心羧酸辅助的 C-H 活化和功能化的计算研究。
Chem Rev. 2017 Jul 12;117(13):8649-8709. doi: 10.1021/acs.chemrev.6b00839. Epub 2017 May 22.
2
Ligand Promoted meta-C-H Chlorination of Anilines and Phenols.配体促进的苯胺和酚的间 C-H 氯化反应。
J Am Chem Soc. 2016 Nov 16;138(45):14876-14879. doi: 10.1021/jacs.6b11055. Epub 2016 Nov 8.
3
Pd/Norbornene: A Winning Combination for Selective Aromatic Functionalization via C-H Bond Activation.
铑（III）催化4-氨基-2-喹诺酮与炔烃的高度位点和区域选择性烯基C-H活化/环化反应——炔烃可逆插入反应
Chem Sci. 2023 Sep 14;14(39):10971-10978. doi: 10.1039/d3sc03987k. eCollection 2023 Oct 11.
4
Total Synthesis of (+)-Cochlearol B by an Approach Based on a Catellani Reaction and Visible-Light-Enabled [2+2] Cycloaddition.基于 Catellani 反应和可见光促进的[2+2]环加成反应策略的 (+)-Cochlearol B 的全合成。
Angew Chem Int Ed Engl. 2022 Aug 1;61(31):e202201213. doi: 10.1002/anie.202201213. Epub 2022 Jun 23.
5
Diversity-oriented functionalization of 2-pyridones and uracils.导向多样性的 2-吡啶酮和尿嘧啶的功能化。
Nat Commun. 2021 May 20;12(1):2988. doi: 10.1038/s41467-021-23058-3.
6
Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis.通过钯/降冰片烯协同催化实现远端烯基碳氢键官能团化
J Am Chem Soc. 2020 Feb 12;142(6):2715-2720. doi: 10.1021/jacs.9b11479. Epub 2020 Feb 3.
7
Redox-neutral -C-H amination of pinacol arylborates palladium(ii)/norbornene catalysis for aniline synthesis.频哪醇芳基硼酸酯的氧化还原中性-C-H胺化反应：钯（II）/降冰片烯催化合成苯胺
Chem Sci. 2019 Jul 23;10(36):8384-8389. doi: 10.1039/c9sc02759a. eCollection 2019 Sep 28.
8
Modular and regioselective synthesis of all-carbon tetrasubstituted olefins enabled by an alkenyl Catellani reaction.通过烯基 Catellani 反应实现全碳四取代烯烃的模块化和区域选择性合成。
Nat Chem. 2019 Dec;11(12):1106-1112. doi: 10.1038/s41557-019-0358-y. Epub 2019 Nov 18.
9
Palladium/Norbornene Cooperative Catalysis.钯/降冰片烯协同催化
Chem Rev. 2019 Jun 26;119(12):7478-7528. doi: 10.1021/acs.chemrev.9b00079. Epub 2019 Apr 25.
钯/降冰片烯：通过 C-H 键活化实现选择性芳基功能化的理想组合。
Acc Chem Res. 2016 Jul 19;49(7):1389-400. doi: 10.1021/acs.accounts.6b00165. Epub 2016 Jun 22.
4
Palladium-catalysed norbornene-mediated C-H functionalization of arenes.钯催化的降冰片烯介导的芳烃 C-H 功能化。
Nat Chem. 2015 Nov;7(11):863-70. doi: 10.1038/nchem.2372.
5
Comparative inhibitory effect of prenylated coumarins, ferulenol and ferprenin, contained in the 'poisonous chemotype' of Ferula communis on mammal liver microsomal VKORC1 activity.阿魏（Ferula communis）“有毒化学型”中所含的异戊烯基香豆素、阿魏醇和阿魏苯素对哺乳动物肝脏微粒体维生素K环氧化物还原酶复合体1（VKORC1）活性的比较抑制作用。
Phytochemistry. 2015 Oct;118:124-30. doi: 10.1016/j.phytochem.2015.08.012. Epub 2015 Aug 24.
6
Direct metal-catalyzed regioselective functionalization of enamides.直接金属催化的烯酰胺区域选择性官能团化反应。
Chemistry. 2014 Jun 16;20(25):7548-64. doi: 10.1002/chem.201402070. Epub 2014 May 26.
7
Catalyst-controlled divergent C-H functionalization of unsymmetrical 2-aryl cyclic 1,3-dicarbonyl compounds with alkynes and alkenes.催化剂控制的不对称 2-芳基环状 1,3-二羰基化合物与炔烃和烯烃的发散 C-H 官能化反应。
J Am Chem Soc. 2013 Jul 24;135(29):10829-36. doi: 10.1021/ja404867k. Epub 2013 Jul 15.
8
A sequential Pd/norbornene-catalyzed process generates o-biaryl carbaldehydes or ketones via a redox reaction or 6H-dibenzopyrans by C-O ring closure.钯/降冰片烯催化的串联反应通过氧化还原反应或 C-O 环闭合生成邻芳基醛或酮或 6H-二苯并吡喃。
Org Lett. 2012 Nov 16;14(22):5792-5. doi: 10.1021/ol302889t. Epub 2012 Nov 7.
9
Pd(II)-catalyzed regioselective 2-alkylation of indoles via a norbornene-mediated C-H activation: mechanism and applications.Pd(II) 催化的吲哚区域选择性 2-烷基化反应：通过降冰片烯介导的 C-H 活化的机理和应用。
J Am Chem Soc. 2012 Sep 5;134(35):14563-72. doi: 10.1021/ja3058138. Epub 2012 Aug 22.
10
Alkylation of pyridone derivatives by nickel/Lewis acid catalysis.镍/路易斯酸催化吡啶酮衍生物的烷基化反应
Angew Chem Int Ed Engl. 2012 Jun 4;51(23):5679-82. doi: 10.1002/anie.201200922. Epub 2012 Apr 19.