Gesellschaft Deutscher Chemiker
Keine Benachrichtigungen
Sie haben noch keine Lesezeichen
Abmelden

Artikel

4,4‐Difluorospiro[2.2]pentan‐1‐yl – A Fluorinated Substituent To Expand the Synthetic and Medicinal Chemists’ Toolbox

Von Wiley-VCH zur Verfügung gestellt

Scalable and diastereoselective synthetic approach to 4,4-difluorospiro[2.2]pentan-1-yl derivatives by the difluorocyclopropanation of (2-methylenecyclopropyl)methanol and further chemical modifications were disclosed. Structural features, pK a, logP, and aqueous solubility of the products were established and compared with those of non-fluorinated and 2,2-difluorinated analogs, as well as monocyclic gem-difluorinated counterparts.


Abstract

Functionalized 4,4-difluorospiro[2.2]pentan-1-yl derivatives are proposed as promising building blocks for synthetic and medicinal chemistry. Scalable, efficient, and diastereoselective approach to their preparation via the difluorocyclopropanation of (2-methylenecyclopropyl)methanol is developed. Stability of the title scaffolds towards common reaction conditions is confirmed by a series of typical functional group transformations. Physicochemical characteristics (pK a, logP, and aqueous solubility) and structural features of the key 4,4-difluorospiro[2.2]pentan-2-yl derivatives are established and compared with those of non-fluorinated analog, 2,2-difluorinated isomer, as well as monocyclic gem-difluorinated counterparts.

Zum Volltext

Überprüfung Ihres Anmeldestatus ...

Wenn Sie ein registrierter Benutzer sind, zeigen wir in Kürze den vollständigen Artikel.