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Chempluschem 2025, e202500150

DOI: 10.1002/cplu.202500150

Chernykh A.; Liashuk O.; Kononenko K.; Michuda A.; Olifir O.; Lesyk D. et al.

Efficient decagram-scale synthesis of (fluoro)alkyl-containing cis-1,2-disubstited cyclobutane-derived building blocks is described. Starting from commercially available chemicals, target cyclobutylamines, carboxylic acids, and other valuable derivatives were obtained in 3–8 steps on up to 39 g scale. Physicochemical characterization of the prepared compounds and their model derivatives revealed 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 suggested the decisive influence of the compounds’ conformation on the discussed properties.

 

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