• 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

2-酰基苯甲酸酯与α,β-不饱和羰基化合物的电还原偶联：产物选择性的密度泛函理论研究

Electroreductive coupling of 2-acylbenzoates with α,β-unsaturated carbonyl compounds: density functional theory study on product selectivity.

作者信息

Kise Naoki, Sakurai Toshihiko

机构信息

Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101, Koyama-cho Minami, Tottori 680-8552, Japan.

出版信息

Beilstein J Org Chem. 2022 Aug 2;18:956-962. doi: 10.3762/bjoc.18.95. eCollection 2022.

DOI:10.3762/bjoc.18.95
PMID:35965855
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9359203/
Abstract

The electroreductive coupling of 2-acylbenzoates with acrylonitrile in the presence of TMSCl and successive treatment with 1 M HCl gave 2-cyanonaphthalen-1-ols or 3-(3-cyanoethyl)phthalides. On the other hand, the reaction of 2-acylbenzoates with methyl vinyl ketone under the same conditions produced 3-(3-oxobutyl)phthalides as the sole products. What determines the product selectivity was studied using DFT calculations.

摘要

在四甲基硅氯（TMSCl）存在下，2-酰基苯甲酸酯与丙烯腈进行电还原偶联反应，随后用1 M盐酸处理，得到2-氰基萘-1-醇或3-(3-氰基乙基)苯酞。另一方面，在相同条件下，2-酰基苯甲酸酯与甲基乙烯基酮反应，仅生成3-(3-氧代丁基)苯酞作为产物。使用密度泛函理论（DFT）计算研究了决定产物选择性的因素。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/8dd1bbd3e613/Beilstein_J_Org_Chem-18-956-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/2666035376cc/Beilstein_J_Org_Chem-18-956-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/3ef6c44ac4ba/Beilstein_J_Org_Chem-18-956-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/df307af84b50/Beilstein_J_Org_Chem-18-956-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/2c2867ee8712/Beilstein_J_Org_Chem-18-956-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/457544f95383/Beilstein_J_Org_Chem-18-956-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/8dd1bbd3e613/Beilstein_J_Org_Chem-18-956-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/2666035376cc/Beilstein_J_Org_Chem-18-956-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/3ef6c44ac4ba/Beilstein_J_Org_Chem-18-956-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/df307af84b50/Beilstein_J_Org_Chem-18-956-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/2c2867ee8712/Beilstein_J_Org_Chem-18-956-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/457544f95383/Beilstein_J_Org_Chem-18-956-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fe5/9359203/8dd1bbd3e613/Beilstein_J_Org_Chem-18-956-g007.jpg

相似文献

1
Electroreductive coupling of 2-acylbenzoates with α,β-unsaturated carbonyl compounds: density functional theory study on product selectivity.2-酰基苯甲酸酯与α,β-不饱和羰基化合物的电还原偶联：产物选择性的密度泛函理论研究
Beilstein J Org Chem. 2022 Aug 2;18:956-962. doi: 10.3762/bjoc.18.95. eCollection 2022.
2
Electroreductive Coupling of Phthalimides with α,β-Unsaturated Carbonyl Compounds and Subsequent Acid-Catalyzed Rearrangement to 4-Aminonaphthalen-1-ols: Density Functional Theory Study of the Acid-Catalyzed Rearrangement of Ketene Silyl Acetals.邻苯二甲酰亚胺与α,β-不饱和羰基化合物的电化学偶联及随后的酸催化重排得到 4-氨基萘-1-醇：烯酮硅基缩醛酸催化重排的密度泛函理论研究。
J Org Chem. 2021 Dec 17;86(24):18232-18246. doi: 10.1021/acs.joc.1c02512. Epub 2021 Dec 6.
3
Electroreductive Coupling of Phthalic Anhydrides with α,β-Unsaturated Carbonyl Compounds: Synthesis of 1,4-Dihydroxynaphthalenes.邻苯二甲酸酐与α,β-不饱和羰基化合物的电化学偶联：1,4-二羟基萘的合成。
J Org Chem. 2020 Nov 6;85(21):13973-13982. doi: 10.1021/acs.joc.0c02000. Epub 2020 Oct 15.
4
Electroreductive coupling of phthalimides with alpha,beta-unsaturated esters: unusual rearrangement of resulting silyl ketene acetals.邻苯二甲酰亚胺与α,β-不饱和酯的电还原偶联：所得甲硅烷基烯酮缩醛的异常重排。
Org Lett. 2009 Nov 5;11(21):4902-5. doi: 10.1021/ol902016a.
5
Density functional theory study of electroreductive hydrocoupling of alpha,beta-unsaturated carbonyl compounds.α,β-不饱和羰基化合物电还原加氢偶联的密度泛函理论研究
J Org Chem. 2006 Nov 24;71(24):9203-7. doi: 10.1021/jo061708k.
6
Electroreductive coupling of optically active α,β-unsaturated carbonyl compounds with diaryl ketones: asymmetric synthesis of 4,5,5-trisubstituted γ-butyrolactones.手性 α,β-不饱和羰基化合物与二芳基酮的电化学偶联：4,5,5-三取代 γ-丁内酯的不对称合成。
Org Lett. 2014 Jun 20;16(12):3348-51. doi: 10.1021/ol5013789. Epub 2014 Jun 5.
7
Electroreductive intermolecular coupling of 3-methoxycarbonylindoles with ketones.3-甲氧基羰基吲哚与酮的电化学分子间偶联。
Org Lett. 2013 Jun 7;15(11):2746-9. doi: 10.1021/ol4010799. Epub 2013 May 17.
8
Unprecedented Diastereoselective Arylogous Michael Addition of Unactivated Phthalides.未活化邻苯二甲酸酯的前所未有的非对映选择性芳基类似迈克尔加成反应。
Chemistry. 2019 May 23;25(29):7131-7141. doi: 10.1002/chem.201900168. Epub 2019 Apr 8.
9
Electroreductive Intermolecular Coupling of Coumarins with Benzophenones: Synthesis of 4-(2-Hydroxyphenyl)-5,5-diaryl-γ-butyrolactones, 2-(2,2-Diaryl-2,3-dihydrobenzofuran-3-yl)acetic Acids, and 4-(Diarylmethyl)coumarins.香豆素与二苯甲酮的电化学分子间偶联反应：4-(2-羟基苯基)-5,5-二芳基-γ-丁内酯、2-(2,2-二芳基-2,3-二氢苯并呋喃-3-基)乙酸和 4-(二芳基甲基)香豆素的合成。
J Org Chem. 2016 Nov 18;81(22):11043-11056. doi: 10.1021/acs.joc.6b02056. Epub 2016 Oct 13.
10
Intracellular Metabolism of α,β-Unsaturated Carbonyl Compounds, Acrolein, Crotonaldehyde and Methyl Vinyl Ketone, Active Toxicants in Cigarette Smoke: Participation of Glutathione Conjugation Ability and Aldehyde-Ketone Sensitive Reductase Activity.α,β-不饱和羰基化合物、丙烯醛、巴豆醛和甲基乙烯基酮在细胞内的代谢，香烟烟雾中的活性毒物：谷胱甘肽结合能力和醛酮敏感还原酶活性的参与
Chem Pharm Bull (Tokyo). 2016;64(6):585-93. doi: 10.1248/cpb.c15-00986.

本文引用的文献

1
Electroreductive Coupling of Phthalimides with α,β-Unsaturated Carbonyl Compounds and Subsequent Acid-Catalyzed Rearrangement to 4-Aminonaphthalen-1-ols: Density Functional Theory Study of the Acid-Catalyzed Rearrangement of Ketene Silyl Acetals.邻苯二甲酰亚胺与α,β-不饱和羰基化合物的电化学偶联及随后的酸催化重排得到 4-氨基萘-1-醇：烯酮硅基缩醛酸催化重排的密度泛函理论研究。
J Org Chem. 2021 Dec 17;86(24):18232-18246. doi: 10.1021/acs.joc.1c02512. Epub 2021 Dec 6.
2
Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp)-H Lactonization of 2-Alkylbenzoic Acids.可见光促进的镁、铁和镍催化实现2-烷基苯甲酸的C(sp)-H内酯化反应
Org Lett. 2021 Aug 6;23(15):5842-5847. doi: 10.1021/acs.orglett.1c01984. Epub 2021 Jul 8.
3
Electroreductive Coupling of Phthalic Anhydrides with α,β-Unsaturated Carbonyl Compounds: Synthesis of 1,4-Dihydroxynaphthalenes.邻苯二甲酸酐与α,β-不饱和羰基化合物的电化学偶联：1,4-二羟基萘的合成。
J Org Chem. 2020 Nov 6;85(21):13973-13982. doi: 10.1021/acs.joc.0c02000. Epub 2020 Oct 15.
4
A Perspective on Organic Electrochemistry.有机电化学的透视
J Org Chem. 2020 Nov 6;85(21):13375-13390. doi: 10.1021/acs.joc.0c01408. Epub 2020 Sep 14.
5
Electrochemical Synthesis of 1-Naphthols by Intermolecular Annulation of Alkynes with 1,3-Dicarbonyl Compounds.通过炔烃与 1,3-二羰基化合物的分子内环化反应电化学合成 1-萘酚。
Org Lett. 2020 Jan 17;22(2):724-728. doi: 10.1021/acs.orglett.9b04549. Epub 2019 Dec 30.
6
Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C-H Bond Activation.
Org Lett. 2019 Aug 16;21(16):6259-6263. doi: 10.1021/acs.orglett.9b02142. Epub 2019 Aug 1.
7
Electrochemical Arylation Reaction.电化学芳基化反应
Chem Rev. 2018 Jul 25;118(14):6706-6765. doi: 10.1021/acs.chemrev.8b00233. Epub 2018 Jul 2.
8
Scalable Electrochemical Dehydrogenative Lactonization of C(sp/sp)-H Bonds.可扩展电化学脱氢内酯化 C(sp/sp)-H 键。
Org Lett. 2018 Jan 5;20(1):252-255. doi: 10.1021/acs.orglett.7b03617. Epub 2017 Dec 7.
9
Use of Electrochemistry in the Synthesis of Heterocyclic Structures.电化学在杂环结构合成中的应用。
Chem Rev. 2018 May 9;118(9):4485-4540. doi: 10.1021/acs.chemrev.7b00271. Epub 2017 Oct 17.
10
Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance.2000年以来的合成有机电化学方法：处于复兴边缘。
Chem Rev. 2017 Nov 8;117(21):13230-13319. doi: 10.1021/acs.chemrev.7b00397. Epub 2017 Oct 9.