Anton V. Chernykh, Oleksandr S. Liashuk, Kyrylo O. Kononenko, Artem Y. Michuda, Oleksandr S. Olifir, Dmytro Lesyk, Karina Turenko, Andrii V. Kozytskyi, Svitlana V. Shishkina, Petro Borysko, Serhiy V. Ryabukhin, Dmytro M. Volochnyuk, Oleksandr O. Grygorenko
{"title":"Synthesis and Physicochemical Properties of Functionalized cis–2-((Fluoro)Alkyl)Cyclobutanes","authors":"Anton V. Chernykh, Oleksandr S. Liashuk, Kyrylo O. Kononenko, Artem Y. Michuda, Oleksandr S. Olifir, Dmytro Lesyk, Karina Turenko, Andrii V. Kozytskyi, Svitlana V. Shishkina, Petro Borysko, Serhiy V. Ryabukhin, Dmytro M. Volochnyuk, Oleksandr O. Grygorenko","doi":"10.1002/cplu.202500150","DOIUrl":null,"url":null,"abstract":"<p>Efficient decagram-scale synthesis of (fluoro)alkyl-containing <i>cis-</i>1,2-disubstituted cyclobutane-derived building blocks is described. Starting from commercially available chemicals, target cyclobutylamines, carboxylic acids, and other valuable derivatives are obtained in 3–8 steps on up to a 39 g scale. Physicochemical characterization of the prepared compounds and their model derivatives reveal the distinct features of <i>cis</i>-1,2-disubstituted cyclobutanes (namely, significantly lowered lipophilicity) as compared to their previously reported <i>trans</i>-isomeric counterparts. Computational analysis, along with experimentally obtained structural properties, suggest the decisive influence of the compounds’ conformation on the discussed properties.</p>","PeriodicalId":148,"journal":{"name":"ChemPlusChem","volume":"90 9","pages":""},"PeriodicalIF":2.8000,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemPlusChem","FirstCategoryId":"92","ListUrlMain":"https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cplu.202500150","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Efficient decagram-scale synthesis of (fluoro)alkyl-containing cis-1,2-disubstituted cyclobutane-derived building blocks is described. Starting from commercially available chemicals, target cyclobutylamines, carboxylic acids, and other valuable derivatives are obtained in 3–8 steps on up to a 39 g scale. Physicochemical characterization of the prepared compounds and their model derivatives reveal the distinct features of cis-1,2-disubstituted cyclobutanes (namely, significantly lowered lipophilicity) as compared to their previously reported trans-isomeric counterparts. Computational analysis, along with experimentally obtained structural properties, suggest the decisive influence of the compounds’ conformation on the discussed properties.
期刊介绍：
ChemPlusChem is a peer-reviewed, general chemistry journal that brings readers the very best in multidisciplinary research centering on chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
Fully comprehensive in its scope, ChemPlusChem publishes articles covering new results from at least two different aspects (subfields) of chemistry or one of chemistry and one of another scientific discipline (one chemistry topic plus another one, hence the title ChemPlusChem). All suitable submissions undergo balanced peer review by experts in the field to ensure the highest quality, originality, relevance, significance, and validity.
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