Synthesis and Physicochemical Properties of trans-2-Fluoroalkyl-Substituted Cyclopentane Building Blocks
Тип публікації :
Препринт
Дата випуску :
5 лютого 2026 р.
Автор(и) :
Bohdan V. Bobovskyi
Oleksandr V. Kudryk
Oleksandr P. Demchuk
Oleksandr V. Hryshchuk
Bohdan S. Sosunovych
Bohdan V. Vashchenko
Dmytro Lesyk
Anton V. Chernykh
Kostiantyn P. Melnykov
Petro Borysko
Igor I. Gerus
Oleksandr O. Grygorenko
eKNUTSHIR URL :
Журнал :
ChemRxiv
Цитування :
[APA 7] Bohdan, V. B., Oleksandr, V. K., Oleksandr, P. D., Oleksandr, V. H., Bohdan, S. S., Bohdan, V. V., Dmytro, L., Anton, V. C., Kostiantyn, P. M., Petro, B., Igor, I. G., & Oleksandr, O. G. (2026). Synthesis and Physicochemical Properties of trans-2-Fluoroalkyl-Substituted Cyclopentane Building Blocks. ChemRxiv,. https://doi.org/10.26434/chemrxiv.10001984/v1
[ДСТУ] Synthesis and Physicochemical Properties of trans-2-Fluoroalkyl-Substituted Cyclopentane Building Blocks / V. B. Bohdan та ін. ChemRxiv. 2026. DOI: 10.26434/chemrxiv.10001984/v1 (дата звернення: 11.09.2026).
A scalable synthesis of trans -1,2-fluoroalkyl-substituted cyclopentane building blocks was developed. The approach relies on orthogonal late-stage functionalization of a common precursor – monoester of trans -1,2-cyclopentanecarboxylic acid. Fluoromethyl-substituted derivatives were accessed via exhaustive reduction of the COOH group, activation of the resulting primary alcohol as a triflate, and nucleophilic substitution with fluoride. Meanwhile, difluoro- and trifluoromethyl groups were introduced through deoxofluorination of the corresponding aldehyde or carboxylic acid. The resulting fluorinated esters were efficiently diversified into a broad range of building blocks relevant to medicinal chemistry, including carboxylic acids, primary amines, azides, alcohols, and sulfonyl chlorides. In addition to the synthetic developments, the effect of the fluoroalkyl substituent (CH 2 F, CHF 2 , CF 3 ) on physicochemical properties of the cyclopentane derivatives was established by measuring p K ₐ and Log P values of model derivatives.
Якщо не вказано інше, ця робота розповсюджується на умовах ліцензії Attribution 4.0 International