Beilstein Journal of Organic Chemistry最新文献_第3页

Redox-active photocatalytic N^C cyclometalated gold(III) catecholate complexes. 氧化还原活性光催化N^C环金属化金（III）儿茶酚酸配合物。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-09-01 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.97

Miguel A Gonzálvez, Sergio Diaz-Alonso, Juan José Gamboa-Carballo, Karinne Miqueu, György Szalóki, Didier Bourissou

引用次数: 0

Bismuth(III)-catalyzed three-component selenation of imidazo[1,2-a]pyridines or related arenes with selenium and arylboronic acids. 铋（III）催化咪唑[1,2-a]吡啶或相关芳烃与硒和芳基硼酸的三组分硒化反应。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-08-28 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.96

Naoki Aiba, Mio Matsumura, Yuki Tada, Yuki Murata, Shuji Yasuike

引用次数: 0

An undecacyclic carbon-centered hydrocarbon radical: synthesis and investigation. 一种非环碳中心烃自由基的合成与研究。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-08-25 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.95

Ali S Acan, Johannes Werner, Joachim Podlech

{"title":"An undecacyclic carbon-centered hydrocarbon radical: synthesis and investigation.","authors":"Ali S Acan, Johannes Werner, Joachim Podlech","doi":"10.3762/bjoc.22.95","DOIUrl":"10.3762/bjoc.22.95","url":null,"abstract":"A stable, cyclopenta-fused polyaromatic hydrocarbon (CP-PAH) radical, comprising six six-membered and five five-membered rings alternately fused within an undecacyclic framework, was synthesized via ortho-fusion of a suitably o,o'-substituted difluorenylfluorene, followed by establishment of the π-conjugated system. The target radical was obtained in eight consecutive synthetic steps with an overall yield of 7%, with a Suzuki coupling and cyclization via electrophilic aromatic substitution (SEAr) serving as key steps. Mesityl substituents attached to the five-membered rings provide kinetic stabilization of the radical species. Comprehensive characterization was performed using EPR spectroscopy, UV-vis spectroscopy, and cyclic voltammetry, further supported by quantum-chemical calculations. The computational studies enabled simulation of the UV-vis spectra and provided insights into spin-density distribution, aromaticity, and frontier orbital energies. The radical is best described by the resonance structure in which the unpaired electron is predominantly localized on the outer cyclopentadiene units, maximizing the number of preserved aromatic benzene sextets. Calculations indicate only a minor triradical contribution to the electronic ground state. Notably, the five-membered rings, particularly the central ring, exhibits pronounced antiaromatic character.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1196-1204"},"PeriodicalIF":2.7,"publicationDate":"2026-08-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13550852/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148910724","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Triazole-based hybrid molecules in anticancer drug discovery: structural classes and mechanistic insights, 2014-2025. 抗癌药物中基于三唑类杂化分子的发现：结构分类和机制洞察，2014-2025。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-08-24 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.94

Meena Bhandari, Akshi Goyal, Deepak Yadav

引用次数: 0

The surprising reaction of (chloro- and methanesulfonyloxy)(phenyl)methylphosphonates and -(phenyl)methylphosphine oxides with potassium diphenylphosphide followed by oxidation. （氯和甲磺酰氧基）（苯基）甲基膦酸盐和-（苯基）甲基膦氧化物与二苯基磷化钾发生氧化反应。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-08-17 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.93

Zsuzsanna Szalai, Janka Bednárik, András Miskó, Angéla Takács, László Kőhidai, László Drahos, György Keglevich

{"title":"The surprising reaction of (chloro- and methanesulfonyloxy)(phenyl)methylphosphonates and -(phenyl)methylphosphine oxides with potassium diphenylphosphide followed by oxidation.","authors":"Zsuzsanna Szalai, Janka Bednárik, András Miskó, Angéla Takács, László Kőhidai, László Drahos, György Keglevich","doi":"10.3762/bjoc.22.93","DOIUrl":"10.3762/bjoc.22.93","url":null,"abstract":"α-Hydroxyphosphonates and α-hydroxyphosphine oxides are important intermediates for additional biologically active species. While (hydroxy(phenyl)methyl)(diphenyl)phosphine oxide did not even undergo chlorination with thionyl chloride, the reaction of diethyl chloro(phenyl)methylphosphonate with potassium diphenylphosphide followed by oxidation with hydrogen peroxide resulted in the expected bis(>P(O)-functionalized) product only as a minor component. The similar reaction of the analogous (methanesulfonyloxy)(phenyl)methyl derivative afforded a mixture of a diethyl (diethoxyphosphonyl)(phenyl)methyl phosphate, a diethyl (diphenylphosphinyl)(phenyl)methyl phosphate, and a ((diphenylphosphinyl)(phenyl)methyl) diphenylphosphinate. The formation of the unexpected products was explained assuming rearrangements and reversible formation of the hydroxymethylene-bis(>P(O)-functionalized) intermediate. Contrary to the earlier experiences, the reaction of ((methanesulfonyloxy)(phenyl)methyl)(diaryl)phosphine oxides with potassium diphenylphosphide followed by oxidation took place in a clear-cut manner providing, with one exception, the corresponding α-phosphinylated α-hydroxyphosphine oxides that could also be synthesized by direct phosphinylation of the starting α-hydroxyphosphine oxide. Cell viability assays performed on U266 myeloma cells revealed concentration-dependent antiproliferative effects of the synthesized compounds on U266 myeloma cells, highlighting the key role of the phosphinoyloxy moiety in the cytotoxic activity, which may be enhanced further by 4-methyl groups in the P-phenyl rings.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1160-1167"},"PeriodicalIF":2.7,"publicationDate":"2026-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13501233/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148811949","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

A cascade synthesis of 2-aminothiochromones from 2-fluorophenyl ketone and thiocarbonyldiimidazole. 由2-氟苯酮和硫羰基二咪唑级联合成2-氨基硫代铬酮。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-08-12 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.92

Kai Zhang, Haofan Shao, Kangjun Liao, Ying Xu, Shimei Du, Yanfang Zhao, Gang Li, Wenzhen Xu, Haihong Huang, Peng Li

引用次数: 0

Construction of CF₂ moieties in FDA-approved drugs (2016-2025): industrial routes, mechanisms, and scale-up considerations. CF2在fda批准的药物中的构建（2016-2025）：工业路线、机制和扩大规模的考虑

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-08-04 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.91

Wenyan Yao, Huanhuan Zhang, Xiaolong Yang, Feng Liu

{"title":"Construction of CF2 moieties in FDA-approved drugs (2016-2025): industrial routes, mechanisms, and scale-up considerations.","authors":"Wenyan Yao, Huanhuan Zhang, Xiaolong Yang, Feng Liu","doi":"10.3762/bjoc.22.91","DOIUrl":"10.3762/bjoc.22.91","url":null,"abstract":"The incorporation of CF2 moieties into drug molecules offers unique advantages in improving metabolic stability and target affinity, making their efficient construction a major focus in pharmaceutical process chemistry. This review systematically examines the synthetic processes of 12 FDA-approved CF2-containing drugs from 2016 to 2025, categorizing them according to the chemical environment of the CF2 group (alkyl-CF2, heteroaryl-CF2, and ArO-CF2). For each drug, the industrial routes for CF2 construction and the reasons for eliminating alternative routes are analyzed. Methods for CF2 formation are classified into two major strategies: fluorinating reagent-based approaches and building block-based approaches. Key process steps and scale-up data are summarized in Table 1. The article systematically discusses four types of reaction mechanisms - nucleophilic fluorination, electrophilic fluorination, radical pathways, and carbene insertion - and evaluates their applicability in industrial production. The analysis shows that for alkyl-CF2 groups, the industry strongly favors preformed CF2 building blocks or indirect fluorination strategies to avoid hazardous reagents and harsh conditions. Continuous flow technology using SF4 has emerged as an important complement to traditional fluorination methods. For heteroaryl-CF2 groups, metal-catalyzed direct introduction of the CF2 unit still faces challenges for industrial application, whereas the difluorocarbene route for ArO-CF2 has been validated. This review provides a reference for process development of new CF2-containing drugs, from strategic design to scale-up evaluation.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1122-1150"},"PeriodicalIF":2.7,"publicationDate":"2026-08-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13454886/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148705329","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Discovery of sugarnitriles A and B, and structural reassignment of SF-2140, from a sugarcane endophytic actinomycete Amycolatopsis sp. JS-O27. 甘蔗内生放线菌Amycolatopsis sp. JS-O27中糖腈A和B的发现及SF-2140的结构重定位。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-07-31 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.90

Qiuyun Li, Ying Liu, Baoyue Wei, Yu Sun, Di Mao, Yanmin Zou, Shan Lu

引用次数: 0

Rhodopyran, a carboxylated hexahydrocyclopenta[b]pyran from Rhodococcus. 红双球菌，一种羧基化的六氢环五[b]吡喃。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-07-28 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.89

Enjuro Harunari, Sara Fushimi, Yasuhiro Igarashi

引用次数: 0

Controlled supramolecular assemblies of luminescent tridentate cyclometalated alkynylgold(III) amphiphiles in aqueous media. 发光三齿环金属化烷基金（III）两亲体在水介质中的受控超分子组装。