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2- and 3-Fluorocyclobutane Building Blocks for Organic and Medicinal Chemistry
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-05-21 , DOI: 10.1002/ejoc.202400493 Andrii Malashchuk 1 , Oleksandr P. Demchuk 2 , Bohdan V. Razhik 3 , Vitalii O. Holumbievskyi 1 , Oleksandr V. Kudryk 4 , Anton V. Chernykh 2 , Oleksandr V. Hryshchuk 1 , Bohdan S. Sosunovych 5 , Dmytro M. Volochnyuk 2 , Bohdan V. Vashchenko 1 , Oleksandr O Grygorenko 6
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-05-21 , DOI: 10.1002/ejoc.202400493 Andrii Malashchuk 1 , Oleksandr P. Demchuk 2 , Bohdan V. Razhik 3 , Vitalii O. Holumbievskyi 1 , Oleksandr V. Kudryk 4 , Anton V. Chernykh 2 , Oleksandr V. Hryshchuk 1 , Bohdan S. Sosunovych 5 , Dmytro M. Volochnyuk 2 , Bohdan V. Vashchenko 1 , Oleksandr O Grygorenko 6
Affiliation
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Multigram synthesis of 2- and 3-monofluorinated cyclobutane building blocks was disclosed. In both cases, fluorocyclobutanecarboxylic acids were the key intermediates used to obtain all other derivatives, e. g., amines, alcohols, bromides, thiols, sulfonyl chlorides, etc. For both target chemotypes, diastereopure cis- and trans-isomers of the corresponding carboxylic acids and amines were obtained through diastereomer separation. Characterization of 2- and 3-fluorocyclobutyl substituents by pKa and LogP measurements for the model derivatives was also performed.
中文翻译：
用于有机化学和药物化学的 2- 和 3-氟环丁烷结构单元
公开了2-和3-单氟化环丁烷结构单元的多克合成。在这两种情况下，氟环丁烷羧酸是用于获得所有其他衍生物（例如胺、醇、溴化物、硫醇、磺酰氯等）的关键中间体。对于这两种目标化学型，相应羧酸的非对映纯顺式和反式异构体以及通过非对映异构体分离得到胺。还通过模型衍生物的pKa和 Log P测量来表征2-和 3- 氟环丁基取代基。
更新日期：2024-05-21
中文翻译：
用于有机化学和药物化学的 2- 和 3-氟环丁烷结构单元
公开了2-和3-单氟化环丁烷结构单元的多克合成。在这两种情况下，氟环丁烷羧酸是用于获得所有其他衍生物（例如胺、醇、溴化物、硫醇、磺酰氯等）的关键中间体。对于这两种目标化学型，相应羧酸的非对映纯顺式和反式异构体以及通过非对映异构体分离得到胺。还通过模型衍生物的pKa和 Log P测量来表征2-和 3- 氟环丁基取代基。
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