Preparation of Fluoroadamantane Acids and Amines: Impact of Bridgehead Fluorine Substitution on the Solution- and Solid-State Properties of Functionalized Adamantanes

Autor:	Robert A. Volkmann, Appleton Troy A, V. John Jasys, and Martine Ziliox, Franco Lombardo, Jon Bordner
Rok vydání:	2000
Předmět:	Chemical shift Adamantane chemistry.chemical_element General Chemistry Carbon-13 NMR Biochemistry Catalysis Hydroxylation Partition coefficient chemistry.chemical_compound Colloid and Surface Chemistry chemistry Lipophilicity Fluorine Electronic effect Organic chemistry
Zdroj:	Journal of the American Chemical Society. 122:466-473
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja992652x
Popis:	Functionalized adamantanes are utilized as medicinal therapeutics and a practical route to novel bridgehead fluorinated adamantylamines and acids including fully fluorinated 3,5,7-tri-fluoroadamantane-1-carboxylic acid 1 and 3,5,7-trifluoroadamantane-1-amine 2 is described. Potassium permanganate-mediated bridgehead hydroxylation followed by DAST fluorination was utilized to sequentially insert bridgehead fluorine atoms. 13C NMR chemical shifts of mono-, di-, and trifluoroadamantylamines, acids and carbamates reveal long-range fluorine-mediated electronic effects within the adamantane framework, most notably by substrates bearing three bridgehead fluorine atoms. The impact of multiple bridgehead fluorine substitution on structure (X-ray crystallography) and on physicochemical parameters such as acidity (pKa) and lipophilicity (log P) which are important for the design of medicinal therapeutics is assessed.
Databáze:	OpenAIRE
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