European Journal of Organic Chemistry最新文献_第6页

Gold‐Catalyzed Cyclization of Indole‐Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles 金催化吲哚系链炔的环化，使外环烯基四氢咔唑的合成成为可能

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-06 DOI: 10.1002/ejoc.70895

Haibo Mei, Jingrui He, Chengting Wang, Jorge Escorihuela, Jianlin Han

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Spring‐Loaded p‐Block Ions: Homodesmotic Ring Strain Energy Benchmarks for Charged Three‐Membered Rings 弹簧加载p -阻滞离子：带电三元环的同动环应变能基准

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-06 DOI: 10.1002/ejoc.70881

Alicia Rey Planells,Ayush V. Agrawal,Arturo Espinosa Ferao

{"title":"Spring‐Loaded p‐Block Ions: Homodesmotic Ring Strain Energy Benchmarks for Charged Three‐Membered Rings","authors":"Alicia Rey Planells,Ayush V. Agrawal,Arturo Espinosa Ferao","doi":"10.1002/ejoc.70881","DOIUrl":"https://doi.org/10.1002/ejoc.70881","url":null,"abstract":"Ring strain energy (RSE) is central to the stability and ring‐opening chemistry of three‐membered rings (3MRs), yet reliable benchmarks for ionic p‐block 3MRs remain scarce. Here, we establish a unified homodesmotic protocol for charged saturated 3MRs: monocationic pnictogeniranium, chalcogeniranium and halonium ions, and monoanionic trieliranides bearing H, F, or Me ligands. A three‐tier workflow, from GFN2‐xTB screening to DLPNO‐CCSD(T)/def2‐QZVPP refinement, is used to compare counter‐ion‐free reactions, Coulomb‐corrected charge‐separated products and explicit ion pairs with SbF 6 − or Cs + . Benchmarking shows that naked‐ion C─C cleavage, or the average of naked‐ion C─C and C─El cleavages where appropriate, gives the most transferable RSE scale while avoiding artifacts from ion pairing. Cationic 3MRs are generally more strained than their neutral analogs, whereas trieliranides show stronger substituent control, with fluorination markedly increasing RSE. The heaviest pnictogeniranium cations (As, Sb, Bi) are best described as pseudocyclic, nonclassical multicentre C 2 Pn frameworks lacking an RCP and displaying Dewar–Chatt–Duncanson‐type structures. Periodic trends are rationalized through lone‐pair‐driven hybridization changes and charge‐dependent bonding. Additive atom and bond strain contributions are reported to enable rapid estimation of RSE in charged p‐block 3MRs.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088495","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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Rigidification of 7‐Aminocoumarins Bearing Electron‐Withdrawing Groups Increases Emission Intensity in Polar Environments 7 -氨基香豆素的刚性承载电子吸出基团增加了极性环境中的发射强度

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-06 DOI: 10.1002/ejoc.70870

Jędrzej Predygier, Mariusz Tasior, Marzena Banasiewicz, Denis Jacquemin, Daniel T. Gryko

{"title":"Rigidification of 7‐Aminocoumarins Bearing Electron‐Withdrawing Groups Increases Emission Intensity in Polar Environments","authors":"Jędrzej Predygier, Mariusz Tasior, Marzena Banasiewicz, Denis Jacquemin, Daniel T. Gryko","doi":"10.1002/ejoc.70870","DOIUrl":"https://doi.org/10.1002/ejoc.70870","url":null,"abstract":"A set of structurally unique coumarins possessing an amino group at position 7 and lactam ring fused to the coumarin lactone ring were synthesized for the first time via Pechmann reaction. The photophysics of these new polarized donor–acceptor dyes were compared with those of structural analogs bearing an ester and amide groups at position 4, revealing significant differences in absorption/emission maxima, solvatofluorochromism and emission intensity. Emission of coumarin‐lactams is blue in cyclohexane and orange in MeOH, whereas coumarin‐esters emit cyan light in cyclohexane and red light in MeOH. Crucially, rigidification of coumarin‐lactams’ skeleton combined with replacement of ester with amide functionality has a profound effect on emission intensity decrease in polar solvents: even in acetonitrile, fluorescence quantum yields are still around 50%. Computational studies probed the nature of the key excited states of all dyes and enabled us to venture the hypothesis that blocking free rotation of electron‐withdrawing group at position 4 is responsible for controlling non‐radiative dissipation of energy in more polar solvents.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"15 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149087386","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

Click Bioconjugation of Aza‐BODIPY Fluorophores to LfcinB Peptides for Improved Biocompatibility 点击Aza - BODIPY荧光团与LfcinB肽的生物偶联以改善生物相容性

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-05 DOI: 10.1002/ejoc.70857

A. Verónica Rodríguez‐Mayor, Maricela Morales, Héctor Manuel Pineda‐Castañeda, Zuly Jenny Rivera‐Monroy, Javier Eduardo García‐Castañeda, Norberto Farfán, Rosa Santillan

{"title":"Click Bioconjugation of Aza‐BODIPY Fluorophores to LfcinB Peptides for Improved Biocompatibility","authors":"A. Verónica Rodríguez‐Mayor, Maricela Morales, Héctor Manuel Pineda‐Castañeda, Zuly Jenny Rivera‐Monroy, Javier Eduardo García‐Castañeda, Norberto Farfán, Rosa Santillan","doi":"10.1002/ejoc.70857","DOIUrl":"https://doi.org/10.1002/ejoc.70857","url":null,"abstract":"Near‐infrared (NIR) organic fluorophores have emerged as promising for biomedical imaging and theragnostics, offering deep‐tissue penetration and reduced background interference. However, poor aqueous solubility and limitations in photostability, biocompatibility, and targeting hinder in vivo applications. Similarly, antimicrobial and anticancer peptides exhibit proteolytic instability and rapid clearance. This study addresses these issues by covalently bioconjugating aza‐BODIPY fluorophores with LfcinB‐derived peptides (RRWQWR, RWQWRWQWR) using CuAAC and thiol‐maleimide click chemistries. Two strategies were compared: (i) CuAAC between azide/alkyne‐functionalized partners, and (ii) Michael addition with cysteine‐containing peptides and AZB‐maleimide . Bioconjugation significantly improved water solubility (calculated LogP 5.3–5.5 → 1.1–4.2; LogS −8.2 → −2.2/−3.7) while preserving NIR photophysical properties ( λ ab s = 703–730 nm). In silico ADMET analysis provided preliminary support for favorable predicted absorption‐related properties and metabolic stability. Thiol‐maleimide constructs showed superior predicted solubility, lower mutagenicity, and more favorable synthetic accessibility than CuAAC analogs. Phase‐contrast microscopy of HeLa cells revealed characteristic apoptotic morphology (cell rounding/shrinkage, membrane association) with blue staining reflecting aza‐BODIPY localization. In parallel, P12 induced caspase activation in flow cytometry assays, providing preliminary evidence of caspase‐associated apoptotic activity. Collectively, these platforms provide a basis for the further development of NIR probes, although their in vivo performance remains to be established experimentally.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149086792","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

Copper‐Catalyzed One‐Pot Approach to 6‐Membered Sultams From Vinyl Sulfonamide Using Methanol as C1 Building Block 以甲醇为C1构建块，铜催化一锅法从乙烯基磺胺中提取6元磺胺

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 DOI: 10.1002/ejoc.70889

Sichun Ai, Xuan Wang, Ruijun Wei, Chenrui Niu, Bo Lv, Yanjie Wang, Min Wang

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Synthetic Applications of Hypervalent Iodine Reagents in Multicomponent Reactions 高价碘试剂在多组分反应中的合成应用

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-25 DOI: 10.1002/ejoc.70803

Jialiang Wu, Yanbing Ji, Jiaxin He, Meiling Tian, Yunfei Du

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Sunscreens as Organic Energy Materials: Macroscopic Heat Release Through Vibrational Relaxation Mechanism 作为有机能量材料的防晒霜：通过振动松弛机制的宏观热释放

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-20 DOI: 10.1002/ejoc.70781

Alejandro García-Eguizábal, Beatriz Peñín, Roberto Peña-Martínez, Ignacio Funes-Ardoiz, Diego Sampedro

{"title":"Sunscreens as Organic Energy Materials: Macroscopic Heat Release Through Vibrational Relaxation Mechanism","authors":"Alejandro García-Eguizábal, Beatriz Peñín, Roberto Peña-Martínez, Ignacio Funes-Ardoiz, Diego Sampedro","doi":"10.1002/ejoc.70781","DOIUrl":"10.1002/ejoc.70781","url":null,"abstract":"<p>Aminocyclohexenimine (ACHI) derivatives are powerful UV-absorbing molecules, long recognized for their unique properties as sunscreens. Here, we demonstrate for the first time the macroscopic heat release through the previously proposed vibrational relaxation mechanism at the molecular level. Thin films of four different ACHI derivatives deposited on quartz substrates produced measurable macroscopic temperature increases (up to 15 °C) under UV and simulated solar irradiation and moderate-to-excellent photothermal stability (maximum half-life of 116 h under continuous UV). While drop-cast films provided proof of concept, spin coating yielded transparent and homogeneous layers that enabled direct monitoring of both thermal and spectroscopic responses in the solid state. These experiments revealed that solid-state absorption spectra, rather than solution-phase properties, correlate best with photothermal performance. The combination of transparency, durability, and efficient light-to-heat conversion highlights ACHI derivatives as a pioneering family of organic photothermal coatings, with potential applications in energy-managing and optically transparent technologies such as smart windows.</p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 37","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148768592","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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Visible-Light-Mediated Synthesis of Biscoumarins Utilizing Photocaged Sulfonic Acid as the Catalyst 以光笼磺酸为催化剂的双香豆素合成研究

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-23 DOI: 10.1002/ejoc.70794

Athina S. J. Shkembi, Stamatis K. Serviou, Valentina Benazzi, Maurizio Fagnoni, Stefano Protti, Christoforos G. Kokotos

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Temperature-Dependent Regiodivergent [3 + 2] Cycloaddition of Azomethine Ylides With (E)-5-Benzylidenethioxoimidazolidin-4-One 温度依赖性区域发散[3 + 2]与(E)‐5‐苄基乙氧基咪唑烷‐4‐1的亚甲亚胺类化合物的环加成

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-23 DOI: 10.1002/ejoc.70773

Supratim Das, Suvendu Maity, Supriyo Halder, Goutam Sinha, Chhanda Mukhopadhyay

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A Novel Scaffold for Liquid Phase Peptide Synthesis 一种新型的液相多肽合成支架

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-20 DOI: 10.1002/ejoc.70793

Luana Lastella, Barbara Biondi, Ivan Guryanov, Marco Macis, Antonio Ricci, Fernando Formaggio

{"title":"A Novel Scaffold for Liquid Phase Peptide Synthesis","authors":"Luana Lastella, Barbara Biondi, Ivan Guryanov, Marco Macis, Antonio Ricci, Fernando Formaggio","doi":"10.1002/ejoc.70793","DOIUrl":"10.1002/ejoc.70793","url":null,"abstract":"<p>The growing number of peptides approved as drugs is pushing the introduction of synthetic methodologies alternative to the solid-phase peptide synthesis (SPPS), currently the most exploited method for large-scale peptide production. Indeed, SPPS is easily scalable, can be automated, and allows the synthesis of long peptides in short times. However, it also has some disadvantages, as it uses large excesses of reagents, huge amounts of solvents (often not “green”), a non-biodegradable solid support, and features a heterogeneous reaction environment in which amino acid couplings are more difficult than in a homogeneous environment. For this reason, in recent years there has been growing interest in developing better synthetic methods. In this work, we present a new dendrimeric support based on lysine (Lys) and short polyethylene glycol (PEG) chains. Its main advantages are (i) the possibility of using more eco-friendly solvents that cannot be used in standard SPPS, (ii) the replacement of polystyrene-based supports with a PEG-lysine hybrid one, and (iii) the formation of a homogeneous reaction medium that will help to reduce the excess of reagents and solvents. The results obtained in the synthesis of a model peptide are promising and amenable to transfer to an industrial scale.</p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 37","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148768822","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