• 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

亚甲蓝作为光氧化还原催化剂:通过单电子转移/能量转移开发合成四氢苯并[]吡喃支架

Methylene Blue as a Photo-Redox Catalyst: The Development Synthesis of Tetrahydrobenzo[]pyran Scaffolds via a Single-Electron Transfer/Energy Transfer.

作者信息

Mohamadpour Farzaneh

机构信息

School of Engineering, Apadana Institute of Higher Education, Shiraz, Iran.

出版信息

Front Chem. 2022 Jul 18;10:934781. doi: 10.3389/fchem.2022.934781. eCollection 2022.

DOI:10.3389/fchem.2022.934781
PMID:35923256
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9339953/
Abstract

In a green tandem reaction using aldehyde derivatives, malononitrile, and dimedone, a radical tandem Knoevenagel-Michael cyclocondensation reaction of tetrahydrobenzo[]pyran scaffolds was developed. Using visible light as a sustainable energy source, methylene blue (MB)-derived photo-excited state functions were employed in an aqueous solution as single-electron transfer (SET) and energy transfer catalysts. The range of yields is quite uniform (81-98%, average 92.18%), and the range of reaction time is very fast (2-7 min, average 3.7 min), and the point mentioned in the discussion is that the procedure tolerates a range of donating and withdrawing groups, while still giving very excellent yields. The reaction is fairly insensitive to the nature of the substituents. Research conducted in this project aims to develop a non-metallic cationic dye that is both inexpensive and widely available for more widespread use. In addition to energy efficiency and environmental friendliness, methylene blue also offers an excellent atom economy, time-saving features, and ease of use. As a result, a wide range of long-term chemical and environmental properties can be obtained. The turnover number and turnover frequency of tetrahydrobenzo[]pyran scaffolds have been computed. Surprisingly, gram-scale cyclization is a possibility, implying that the technology may be applied in industries.

摘要

在使用醛衍生物、丙二腈和双甲酮的绿色串联反应中,开发了一种四氢苯并[]吡喃支架的自由基串联Knoevenagel - Michael环缩合反应。以可见光作为可持续能源,亚甲基蓝(MB)衍生的光激发态功能在水溶液中用作单电子转移(SET)和能量转移催化剂。产率范围相当均匀(81 - 98%,平均92.18%),反应时间范围非常快(2 - 7分钟,平均3.7分钟),讨论中提到的一点是该方法能耐受一系列供电子和吸电子基团,同时仍能给出非常优异的产率。该反应对取代基的性质相当不敏感。本项目开展的研究旨在开发一种既廉价又广泛可得、可供更广泛使用的非金属阳离子染料。除了能源效率和环境友好性外,亚甲基蓝还具有出色的原子经济性、省时特性和易用性。因此,可以获得广泛的长期化学和环境性质。已经计算了四氢苯并[]吡喃支架的周转数和周转频率。令人惊讶的是,克级环化是可能的,这意味着该技术可能应用于工业。

相似文献

1
Methylene Blue as a Photo-Redox Catalyst: The Development Synthesis of Tetrahydrobenzo[]pyran Scaffolds via a Single-Electron Transfer/Energy Transfer.亚甲蓝作为光氧化还原催化剂:通过单电子转移/能量转移开发合成四氢苯并[]吡喃支架
Front Chem. 2022 Jul 18;10:934781. doi: 10.3389/fchem.2022.934781. eCollection 2022.
2
The development of imin-based tandem Michael-Mannich cyclocondensation through a single-electron transfer (SET)/energy transfer (EnT) pathway in the use of methylene blue (MB) as a photo-redox catalyst.以亚甲基蓝(MB)作为光氧化还原催化剂,通过单电子转移(SET)/能量转移(EnT)途径开发基于亚胺的串联迈克尔-曼尼希环缩合反应。
RSC Adv. 2022 Apr 6;12(17):10701-10710. doi: 10.1039/d2ra01190e. eCollection 2022 Mar 31.
3
A new role for concentrated solar radiation (CSR) as a renewable heat source for the catalyst-solvent free synthesis of tetrahydrobenzo[b]pyran scaffolds.集中太阳能辐射(CSR)在无催化剂和溶剂条件下合成四氢苯并[b]吡喃支架中的新作用:一种可再生热源。
Sci Rep. 2023 Jul 17;13(1):11485. doi: 10.1038/s41598-023-38662-0.
4
The development of Friedländer heteroannulation through a single electron transfer and energy transfer pathway using methylene blue (MB).通过使用亚甲蓝(MB)的单电子转移和能量转移途径实现弗里德兰德杂环化反应的发展。
Sci Rep. 2022 May 4;12(1):7253. doi: 10.1038/s41598-022-11349-8.
5
New Role for Photoexcited Na Eosin Y the Direct Hydrogen Atom Transfer Process in Photochemical Visible-Light-Induced Synthesis of 2-Amino-4-Chromene Scaffolds Under Air Atmosphere.光激发的钠曙红Y在空气氛围下光化学可见光诱导合成2-氨基-4-色烯骨架中的直接氢原子转移过程的新作用
Front Chem. 2022 Jun 9;10:880257. doi: 10.3389/fchem.2022.880257. eCollection 2022.
6
Photochemical synthesis of pyrano[2,3-d]pyrimidine scaffolds using photoexcited organic dye, Na eosin Y as direct hydrogen atom transfer (HAT) photocatalyst via visible light-mediated under air atmosphere.在空气气氛下,通过可见光介导,使用光激发有机染料(曙红Y钠)作为直接氢原子转移(HAT)光催化剂,进行吡喃并[2,3-d]嘧啶支架的光化学合成。
BMC Chem. 2023 Feb 7;17(1):2. doi: 10.1186/s13065-023-00912-7.
7
Introduction of Succinimide as A Green and Sustainable Organo-Catalyst for the Synthesis of Arylidene Malononitrile and Tetrahydrobenzo[b] pyran Derivatives.介绍琥珀酰亚胺作为一种绿色可持续的有机催化剂,用于合成芳亚甲基丙二腈和四氢苯并[b]吡喃衍生物。
Comb Chem High Throughput Screen. 2021;24(1):155-163. doi: 10.2174/1386207323666200709170916.
8
A Simple and One-pot Synthesis of Tetrahydrobenzo[b]pyrans and Spirooxindoles Catalyzed by H-Fe3O4@DA-SO3H as an Efficient, Light and Reusable Nanocatalyst.以H-Fe3O4@DA-SO3H为高效、光响应且可重复使用的纳米催化剂,实现四氢苯并[b]吡喃和螺环氧化吲哚的简单一锅法合成。
Comb Chem High Throughput Screen. 2018;21(7):487-494. doi: 10.2174/1386207321666180817142658.
9
Acridine yellow G (AYG) as a photo-induced electron transfer (PET) photocatalyst employed for the radical Michael-Mannich cyclocondensation of imines.吖啶黄G(AYG)作为一种光诱导电子转移(PET)光催化剂,用于亚胺的自由基迈克尔-曼尼希环缩合反应。
Front Chem. 2022 Oct 6;10:1015330. doi: 10.3389/fchem.2022.1015330. eCollection 2022.
10
Synthesis of polyfunctionalized dihydro-2-oxypyrroles catalyzed by 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a novel donor-acceptor fluorophore.以新型供体-受体荧光团1,2,3,5-四(咔唑-9-基)-4,6-二氰基苯(4CzIPN)催化合成多官能化二氢-2-氧代吡咯。
Sci Rep. 2022 Oct 7;12(1):16911. doi: 10.1038/s41598-022-20689-4.

引用本文的文献

1
Visible-light-driven radical Friedländer hetero-annulation of 2-aminoaryl ketone and α-methylene carbonyl compound via organic dye fluorescein through a single-electron transfer (SET) pathway.通过单电子转移(SET)途径,利用有机染料荧光素实现2-氨基芳基酮与α-亚甲基羰基化合物的可见光驱动自由基Friedländer杂环化反应。
BMC Chem. 2022 Dec 15;16(1):116. doi: 10.1186/s13065-022-00910-1.
2
Acridine yellow G (AYG) as a photo-induced electron transfer (PET) photocatalyst employed for the radical Michael-Mannich cyclocondensation of imines.吖啶黄G(AYG)作为一种光诱导电子转移(PET)光催化剂,用于亚胺的自由基迈克尔-曼尼希环缩合反应。
Front Chem. 2022 Oct 6;10:1015330. doi: 10.3389/fchem.2022.1015330. eCollection 2022.

本文引用的文献

1
The development of Friedländer heteroannulation through a single electron transfer and energy transfer pathway using methylene blue (MB).通过使用亚甲蓝(MB)的单电子转移和能量转移途径实现弗里德兰德杂环化反应的发展。
Sci Rep. 2022 May 4;12(1):7253. doi: 10.1038/s41598-022-11349-8.
2
The development of imin-based tandem Michael-Mannich cyclocondensation through a single-electron transfer (SET)/energy transfer (EnT) pathway in the use of methylene blue (MB) as a photo-redox catalyst.以亚甲基蓝(MB)作为光氧化还原催化剂,通过单电子转移(SET)/能量转移(EnT)途径开发基于亚胺的串联迈克尔-曼尼希环缩合反应。
RSC Adv. 2022 Apr 6;12(17):10701-10710. doi: 10.1039/d2ra01190e. eCollection 2022 Mar 31.
3
Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis.
电化学和光氧化还原催化:在有机合成中的比较评价。
Molecules. 2019 Jun 5;24(11):2122. doi: 10.3390/molecules24112122.
4
Organic Photoredox Catalysis.有机光氧化还原催化。
Chem Rev. 2016 Sep 14;116(17):10075-166. doi: 10.1021/acs.chemrev.6b00057. Epub 2016 Jun 10.
5
Understanding the Kinetics and Spectroscopy of Photoredox Catalysis and Transition-Metal-Free Alternatives.理解光氧化还原催化和无过渡金属替代物的动力学和光谱学。
Acc Chem Res. 2016 Jun 21;49(6):1320-30. doi: 10.1021/acs.accounts.6b00012. Epub 2016 Mar 29.
6
Methylene blue in photodynamic therapy: From basic mechanisms to clinical applications.亚甲蓝在光动力疗法中的应用:从基础机制到临床应用。
Photodiagnosis Photodyn Ther. 2005 Sep;2(3):175-91. doi: 10.1016/S1572-1000(05)00097-9. Epub 2005 Nov 21.
7
A vicious circle: role of oxidative stress, intraneuronal Abeta and Cu in Alzheimer's disease.恶性循环:氧化应激、神经元内β淀粉样蛋白和铜在阿尔茨海默病中的作用
Clin Neuropathol. 2006 Jul-Aug;25(4):163-71.
8
Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening.通过基于受体的虚拟筛选鉴定化学结构多样的Chk1抑制剂。
Bioorg Med Chem. 2006 Jul 15;14(14):4792-802. doi: 10.1016/j.bmc.2006.03.021. Epub 2006 Mar 29.
9
Methylene blue.亚甲蓝
Am J Ther. 2003 Jul-Aug;10(4):289-91. doi: 10.1097/00045391-200307000-00009.
10
Methylene Blue--a therapeutic dye for all seasons?亚甲蓝——四季通用的治疗性染料?
J Chemother. 2002 Oct;14(5):431-43. doi: 10.1179/joc.2002.14.5.431.