Organic & Biomolecular Chemistry最新文献_第4页

Chemoselective electrochemical hydrogenation of α,β-unsaturated carbonyl compounds using methanol as a hydrogen source and a nail anode. 以甲醇为氢源和钉阳极的α，β-不饱和羰基化合物的化学选择性电化学加氢。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob01246a

Runsen Xu, Fang Wang, Mingming Yang, Xiaobin Lin, Yanzhong Zhen, Ziwei Gao

{"title":"Chemoselective electrochemical hydrogenation of α,β-unsaturated carbonyl compounds using methanol as a hydrogen source and a nail anode.","authors":"Runsen Xu, Fang Wang, Mingming Yang, Xiaobin Lin, Yanzhong Zhen, Ziwei Gao","doi":"10.1039/d6ob01246a","DOIUrl":"10.1039/d6ob01246a","url":null,"abstract":"An electrochemical reductive hydrogenation of α,β-unsaturated carbonyl compounds has been developed using an undivided cell with a nail anode and a graphite rod cathode in CH3OH containing 0.1 M TBAPF6 at a constant current of 20 mA. The protocol accommodates a broad range of substrates, including chalcones, conjugated dienones, and alkynones, affording the corresponding saturated ketones in yields ranging from 73% to 96%. The reaction exhibits remarkable chemoselectivity toward CC and CC bonds over carbonyl groups and carbon-halogen bonds, as demonstrated by the complete retention of ketones and chloro, bromo, methoxy, and methyl substituents. Deuterium labeling experiments using CH3OD as the deuterium source confirm that the solvent serves as the exclusive hydrogen/deuterium source and provide a cost-effective route to deuterium-labeled ketones. Mechanistic insights from DFT calculations reveal that the LUMO energy levels and orbital distributions correlate well with the observed reactivity and regioselectivity trends, offering a rational basis for understanding the electrochemical reduction process.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8154-8162"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149101174","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

Efficient synthesis of H-phosphonates by transesterification of diphenyl H-phosphonate with lipid alcohols in the absence of a solvent or catalyst. 在没有溶剂或催化剂的情况下，用氢膦酸二苯酯与脂质醇酯交换反应高效合成氢膦酸盐。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob00519e

Chloé Le Roux, Mariam Simonnin, Antony Jozić, Mathieu Berchel, Hélène Couthon, Gaurav Sahay, Paul-Alain Jaffrès

引用次数: 0

Recent advances in the thioglycosylation of indoles and tryptophan: strategies and applications in natural product synthesis. 吲哚和色氨酸巯基化的最新进展：策略及其在天然产物合成中的应用。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob01085g

Shalini, Eram Fatima, Toshima Chouhan, Pratyusha Barman, Pintu Kumar Mandal

{"title":"Recent advances in the thioglycosylation of indoles and tryptophan: strategies and applications in natural product synthesis.","authors":"Shalini, Eram Fatima, Toshima Chouhan, Pratyusha Barman, Pintu Kumar Mandal","doi":"10.1039/d6ob01085g","DOIUrl":"10.1039/d6ob01085g","url":null,"abstract":"Thioglycosylated indoles and tryptophan derivatives represent an important class of sulfur-containing compounds with increasing significance in natural product synthesis, medicinal chemistry, and chemical biology. The development of efficient and selective C-S bond-forming methods has enabled access to structurally diverse thioglycosides and expanded their applications in the synthesis of biologically relevant molecules. The recent discovery of isatindigotindolosides I-IV from Radix isatidis, which exhibit anti-inflammatory and antiviral activities, has further stimulated interest in thioglycosylation strategies for the synthesis of biologically relevant indole derivatives. This review summarizes recent advances in the C2- and C3-thioglycosylation of indoles, tryptophan, and tryptophan-containing peptides. Particular attention is given to the use of N-(thioglycosyl)succinimides, glycosyl thiosulfonates, and glycosyl thiols as sulfenylating agents, with emphasis on reaction design, substrate scope, regioselectivity, mechanistic aspects, and synthetic applications. Representative applications in natural product synthesis, including the total synthesis of isatindigotindolosides I-IV, are also highlighted. Overall, these advances demonstrate the current state of thioglycosylation as a powerful approach for accessing structurally diverse and pharmaceutically relevant sulfur-containing indole derivatives and provide insights into future opportunities for the development of more efficient, selective, and broadly applicable thioglycosylation methods.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8029-8043"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149035568","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

Electronic and steric control of meso-tetraaryl porphycene tautomerism via regioselective β-functionalization. 通过区域选择性β功能化控制中四芳基卟啉互变异构的电子和空间控制。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob00853d

Debasish Mandal, Bhuban Mohan Bebarta, Mangalampalli Ravikanth

{"title":"Electronic and steric control of meso-tetraaryl porphycene tautomerism via regioselective β-functionalization.","authors":"Debasish Mandal, Bhuban Mohan Bebarta, Mangalampalli Ravikanth","doi":"10.1039/d6ob00853d","DOIUrl":"https://doi.org/10.1039/d6ob00853d","url":null,"abstract":"Herein, we establish the first synthetic strategy for the direct β-C-H nitration of a free base meso-tetraaryl porphycene using HNO3 in CHCl3 in a selective and controlled manner. The reaction affords two regioisomers of the β-nitro porphycene (regioselectivity upto β : β' = 3 : 7) without the formation of any over-nitrated products or compromising the integrity of the macrocycle. Beyond synthetic access, β-functionalization enables precise electronic and steric modulation of the porphycene macrocycle, resulting in distinct optical properties, including enhanced Q-band absorption and red-shifted near-infrared (NIR) fluorescence extending up to 720 nm with good quantum yields. Moreover, comprehensive spectroscopy, X-ray crystallography, and computational studies revealed that the β-selective nitration shows a strong electronic bias on the intrinsically rapid N-H tautomerization, establishing a highly biased equilibrium that majorly favours a single tautomeric state at room temperature within the rectangular cavity of the porphycene. Furthermore, the reduction of the electron-deficient β-nitro porphycene to an electron-rich β-amino porphycene reverses the electronic perturbation and favours the opposite tautomeric form. This simple protocol provides electronically tuned β-functionalized porphycenes that not only serve as promising building blocks to design molecular systems for finely tuned NIR emissive optoelectronics, biological and material applications, but also act as model substrates to study the fundamentally important hydrogen transfer in porphycene macrocycles.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177911","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

Ruthenium-catalyzed asymmetric transfer hydrogenation of [2.2]paracyclophanecarboxaldehydes via kinetic resolution. 钌催化的[2.2]副环蒽醛的不对称转移加氢动力学分解。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob01308b

Yu Yang, Jia-Xuan Wang, Hao-Dong Chen, Chang Chen, Yong-Gui Zhou, Bo Wu, Chang-Bin Yu

引用次数: 0

Electrochemical C4-C4' homocoupling of 2-arylpyridines. 2-芳基吡啶的电化学C4-C4′均偶联。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob01238h

Jialing Zhang, Zishen Song, Li Wang, Laizheng Luo, Yuxiang Gao, Jinwei Zhang, Weisi Guo

引用次数: 0

Synthesis of β,N-diphosphoryl-substituted α-aminocinnamates via the C,N-diphosphorylation of 2H-azirines. 2h -氮嘧啶C， n -二磷酸化合成β， n -二磷酸基取代α-氨基氨基酸酯。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob01327a

Ilya A Romanenko, Anastasiya V Agafonova, Ilya A Smetanin, Maksim A Valiarovskii, Alexander F Khlebnikov, Mikhail S Novikov

引用次数: 0

Ternary deep eutectic solvent-mediated direct amidation of carboxylic acids. 三元深共晶溶剂介导的羧酸直接酰胺化。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob01305h

Yumiao Zhao, Yujia Jiang, Xiaoqiang Yu

引用次数: 0

Studies on the convenient synthesis, fluorescence properties and bioactivity of chromenonitriles. 铬腈的便捷合成、荧光性质及生物活性研究。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob01096b

Sheng-Yu Li, Zhong-Hao Li, Chu-Ming Pang, Ye-Tong Liu, Bo-Wen Wang, Zu-Qi Zhang, Ying-Jun Zhang, Zhao-Yang Wang

{"title":"Studies on the convenient synthesis, fluorescence properties and bioactivity of chromenonitriles.","authors":"Sheng-Yu Li, Zhong-Hao Li, Chu-Ming Pang, Ye-Tong Liu, Bo-Wen Wang, Zu-Qi Zhang, Ying-Jun Zhang, Zhao-Yang Wang","doi":"10.1039/d6ob01096b","DOIUrl":"https://doi.org/10.1039/d6ob01096b","url":null,"abstract":"The synthesis of chromenonitriles remains largely underexplored, primarily due to the limited availability of suitable substrates and the generally unsatisfactory yields of existing methods. Herein, we report a new method that enables the efficient construction of chromenonitriles under mild, metal-free conditions, using readily accessible chromones and benzoylacetonitriles as starting materials. This transformation is driven by a Knoevenagel condensation co-catalyzed by pyridine and 1,4-diazabicyclo[2.2.2]octane (DABCO), affording the desired products in good yields. In addition to the reported compounds 3a, 3d and 3h, 23 other new compounds are also successfully synthesized. Photophysical characterization reveals that the synthesized compounds exhibit intense yellow-green fluorescence and pronounced aggregation-induced emission (AIE) behaviour, observable both in a dilute solution and the solid state. Dynamic light scattering analysis confirms the correlation between aggregation and fluorescence enhancement, and DFT calculations rationalize the observed photophysical behaviour. Antibacterial activity tests show that they have the potential to become fluorescent probes with antibacterial ability.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"24 39","pages":"8093-8100"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177912","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

A practical guide to atropisomerism: fundamentals and case studies from modern drug discovery. 萎缩异构的实用指南：现代药物发现的基础和案例研究。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob01244b

Mariami Basilaia, Andrew M O'Brien, Michael R Rufrano, Jeffrey L Gustafson

{"title":"A practical guide to atropisomerism: fundamentals and case studies from modern drug discovery.","authors":"Mariami Basilaia, Andrew M O'Brien, Michael R Rufrano, Jeffrey L Gustafson","doi":"10.1039/d6ob01244b","DOIUrl":"https://doi.org/10.1039/d6ob01244b","url":null,"abstract":"Atropisomerism is a form of axial chirality that arises when rotation about a single bond is sufficiently restricted to render the enantiomeric conformers configurationally stable and isolable. Because bond rotation provides a spontaneous pathway for racemization, atropisomers span an extraordinary range of stereochemical stabilities-from species that racemize within seconds at room temperature to compounds predicted to retain their configuration for milenia under any pharmaceutically relevant conditions. Although atropisomerism is most commonly associated with biaryl scaffolds, it can arise across a remarkably diverse range of molecular architectures. Many of these have emerged as privileged pharmaceutical scaffolds, making atropisomerism an increasingly important consideration in medicinal chemistry, with more than 20 configurationally stable atropisomeric drug candidates currently in clinical development worldwide. Consequently, atropisomerism has evolved from a topic of primarily academic interest into a common and practical challenge in modern drug discovery and development. In this review, we discuss the challenges associated with the discovery, development, and manufacturing of atropisomeric drug candidates, culminating in a survey of the strategies used to establish atropisomeric axes on process scale for approved drugs and compounds currently undergoing clinical evaluation. We hope this review will serve as both a practical resource and a source of inspiration for chemists developing the next generation of atropisomerically pure pharmaceuticals.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177897","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