European Journal of Organic Chemistry最新文献_第8页

Fast Nucleophilic Approach to Exhaustively Substituted Porphyrin Derivatives at the “Eastern Half” “东半部”全取代卟啉衍生物的快速亲核方法

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-25 DOI: 10.1002/ejoc.202401054

Agnieszka Mikus, Sylwia Ostrysz, Stanisław Ostrowski

{"title":"Fast Nucleophilic Approach to Exhaustively Substituted Porphyrin Derivatives at the “Eastern Half”","authors":"Agnieszka Mikus, Sylwia Ostrysz, Stanisław Ostrowski","doi":"10.1002/ejoc.202401054","DOIUrl":"https://doi.org/10.1002/ejoc.202401054","url":null,"abstract":"<i>meso</i>-Tetraarylporphyrin chelates (of Zn<sup>2+</sup>, Ni<sup>2+</sup>, and Cu<sup>2+</sup>) are easily available from parent porphyrins. Their reactions with nitric acid (yellow fuming HNO<sub>3</sub>, <i>d</i> = 1.52, diluted to 25%–50%), under optimized conditions in CHCl<sub>3</sub> at room temperature, can be carried out selectively, thus giving mainly <i>β</i>,<i>β</i>-dinitro-substituted moieties (usually two or three isomers of the above complexes). These intermediates (obtained in overall yields of up to 73%), upon the reaction with carbanions bearing a leaving group <i>X</i> at the reactive center, afford the target products, the ones of vicarious nucleophilic substitution (VNS) of hydrogen. This approach allows the synthesis of porphyrin derivatives exhaustively <i>β</i>-substituted in the so-called “Eastern half”, starting from a simple <i>meso-</i>tetraarylporphyrins. These types of products are sought in anticancer photodynamic therapy (PDT). Thus, the above two-step procedure including very attractive VNS reaction gives hydrophilic or amphiphilic moieties that seem to be potential PDT agents with unique structures, being practically unavailable by any other alternative methods.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145134248","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Front Cover: Mild Photocatalytic Hydrodecarboxylation of Fatty Acid Derivatives using Xanthene Dyes for Biomass Valorization (Eur. J. Org. Chem. 34/2025) 前封面：使用杂蒽染料进行脂肪酸衍生物的轻度光催化加氢脱羧，用于生物质增值。j . Org。化学34/2025)

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-24 DOI: 10.1002/ejoc.70118

Jhudson G. L. de Araujo, Thays L. Lemos, Walber M. de O. Domingos, Maria do S. B. da Silva, Pedro H. do N. Silva, Aecia S. D. dos Anjos, Carlos A. Martínez-Huitle, Elisama V. dos Santos, Amanda D. Gondim, Lívia N. Cavalcanti

引用次数: 0

Visible‐Light‐Induced α‐C(sp3)‐H Alkylation of 1,3,4‐Oxadiazoles via 1,2‐Hydrogen Atom Transfer 可见光诱导1,2 -氢原子转移1,3,4 -恶二唑的α - C(sp3) - H烷基化反应

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500605

Yafei Zhu , Dongqin He , Hui Sun , Mi Wang , Cuimei Zhang , Jian Chen , Guanghui Lv , Yong Wu

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Front Cover: Novel Ambergris Odorants Devoid of Ketal Functions: Sustainable Synthesis of 4-(α-Cedren-8-yl)Butan-2-Ones and Potent Methoxy Derivatives by Claisen Chemistry (Eur. J. Org. Chem. 33/2025) 封面：新型无酮功能龙香气味剂：clisen化学可持续合成4-（α-雪松-8-基）丁酮-2- 1和有效的甲氧基衍生物。j . Org。化学33/2025)

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.70084

Elisa Kuhnt, Marc Mansfeld, Philip Kraft

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Site‐Selective CH Amination of Lupane‐Type Triterpenoids Lupane型三萜的位点选择性C - H胺化

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500340

Vladislavs Kroškins , Jevgeņija Lugiņina , Rihards Lācis , Anatoly Mishnev , Māris Turks

引用次数: 0

Facile Synthesis of 5‐Halo‐1,2,3‐Triazole‐Fused Benzotricyclic Frameworks from 1‐(ω‐Azidoalkyl)‐2‐(2,2‐Dihalovinyl)Arenes and their Application in Fluorescent Triazole Derivatives 1-（ω-叠氮烷基）-2-（2,2-二卤乙烯基）芳烃催化合成5- halo -1,2,3-三唑-并杂三环骨架及其在荧光三唑衍生物中的应用

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500355

Seiya Kikukawa , Miki Ebihara , Kazuki Kobayashi , Nozomi Kasakura , Takashi Kanamori , Tadaomi Furuta , Ai Kohata , Nobuaki Funahashi , Shota Matsumoto , Satoru Karasawa , Kazushi Kinbara , Naohiko Koshikawa , Hideya Yuasa , Takeshi Hata

{"title":"Facile Synthesis of 5‐Halo‐1,2,3‐Triazole‐Fused Benzotricyclic Frameworks from 1‐(ω‐Azidoalkyl)‐2‐(2,2‐Dihalovinyl)Arenes and their Application in Fluorescent Triazole Derivatives","authors":"Seiya Kikukawa , Miki Ebihara , Kazuki Kobayashi , Nozomi Kasakura , Takashi Kanamori , Tadaomi Furuta , Ai Kohata , Nobuaki Funahashi , Shota Matsumoto , Satoru Karasawa , Kazushi Kinbara , Naohiko Koshikawa , Hideya Yuasa , Takeshi Hata","doi":"10.1002/ejoc.202500355","DOIUrl":"10.1002/ejoc.202500355","url":null,"abstract":"<div><div>By heating 1‐(ω‐azidoalkyl)‐2‐(2,2‐dihalovinyl)arenes in DMF, intramolecular Huisgen cycloaddition between the azido group and the 1,1‐dihalovinyl moiety proceeds smoothly to afford 5‐halo‐1,2,3‐triazole‐fused tricyclic benzocondensed compounds. Leveraging the remaining halogen groups, the carbon chain extension via the Mizoroki–Heck or Suzuki–Miyaura coupling reactions, followed by an intramolecular Friedel–Crafts reaction, furnish polycyclic systems that incorporate fused triazole rings. Furthermore, the transformation of the halogen groups into the 2‐nitrobenzene derivatives via Suzuki–Miyaura cross‐coupling, followed by a Cadogan reaction using triphenylphosphine, provides a series of fluorescent pentacyclic compounds.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 34","pages":"Article e202500355"},"PeriodicalIF":2.7,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144278652","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Kinetic Resolution of Secondary Alcohols Using Connon Type Catalysts 用Connon型催化剂动力学拆分仲醇

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500733

Caroline M. Carter , Hendrik Zipse

引用次数: 0

Fluorescent β‐Sheet‐Based Peptide Hydrogels with Aggregation‐Enhanced Emission Properties 具有聚集增强发射特性的基于β -薄片的荧光肽水凝胶

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500730

Jolien Bertouille , Adelaide R. Mashweu , François J. De Beer , Charlotte Yvanoff , Ronnie G. Willaert , Steven Ballet , Charlotte Martin , Vladimir A. Azov , Ulrich Hennecke

{"title":"Fluorescent β‐Sheet‐Based Peptide Hydrogels with Aggregation‐Enhanced Emission Properties","authors":"Jolien Bertouille , Adelaide R. Mashweu , François J. De Beer , Charlotte Yvanoff , Ronnie G. Willaert , Steven Ballet , Charlotte Martin , Vladimir A. Azov , Ulrich Hennecke","doi":"10.1002/ejoc.202500730","DOIUrl":"10.1002/ejoc.202500730","url":null,"abstract":"<div><div>Novel fluorescent peptide hydrogels are reported by combining 1,8‐naphthalimide‐derived amino acids with a previously developed peptide‐based controlled drug release matrix. Aggregation‐enhanced emission is achieved by inserting the fluorescent naphthalimide moieties in a peptide sequence with self‐assembling properties. The formation of β‐sheets directs the orientation of the luminescent side chains, leading to the avoidance of aggregation‐caused quenching. The relation between the β‐sheet‐underpinned fiber formation and the emission characteristics is further elucidated by spectroscopic and microscopic techniques, including correlative fluorescence and atomic force microscopy imaging. Owing to the incorporation of the naphthalimide moiety, the gelation concentration is lowered and the gel strength improved. The resulting hydrogels does not contain any organic solvent (in contrast to ample literature examples), present thixotropic behavior, and the fluorescent properties are sensitive to environmental conditions such as temperature and medium. These features make the soft biomaterials interesting for applications such as biosensing, real‐time bioimaging, and 3D printing. The high tunability of the peptide sequence composition and configuration, as well as the chemical structure of the 1,8‐naphthalimide moiety, allows for modulating the material toward desired properties.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 34","pages":"Article e202500730"},"PeriodicalIF":2.7,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144763496","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Nucleophilic Substitution of Alkyl Halides with Secondary Phosphine Oxides under Solvent‐Free Conditions for the Synthesis of Tertiary Phosphine Oxides 在无溶剂条件下，烷基卤化物与仲膦氧化物的亲核取代合成叔膦氧化物

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500229

Yuying Chen , Xiaoyu Yan , Jing Yu , Yingying Su , Zheng Liu , Mengcheng Zhang , Xiantao Ma

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A Concave Mirror Photoreactor Design for Visible‐Light Photocatalysis 一种用于可见光光催化的凹面镜光反应器设计

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500568

Marko Slijepcevic , Milica Plazinic , Filip Bihelovic , Bojan Vulovic

引用次数: 0