Synthesis and Analysis of (γ,γ',γ''-Trifluoro)neopentyl (TFNP) Aryl Ethers as a Polar Fluoroaliphatic Motif

Autor(es)

Tarui, Atsushi ; Piscelli, Bruno A. ; Al-Maharik, Nawaf ; Stewart, Josephine M. ; Niemcova, Patricie ; Cordes, David B. ; Mckay, Aidan P. ; Murphy, Cormac D. ; Cormanich, Rodrigo A. ; Hagan, David O'

• Tipo de documento: Artigo Científico
• Fonte: CHEMISTRY-A EUROPEAN JOURNAL; v. 30, n. 57, p. 5-pg., 2024-09-24.

Resumo

A route is developed to (gamma,gamma',gamma'''-trifluoro)neopentyl (TFNP) aryl ethers to extend the methods for the introduction of the tert-butyl group, carrying a fluorine on each of the methyl substituents. The route combines neopentyltosylate 3 with phenols and thiophenols to give efficient substitution reactions to the corresponding TFNP aryl ethers. The three C-F bonds adopt a helical propeller conformation as revealed by computation and single crystal X-ray structure analysis. The LogPs of TFNP ethers are lower (more hydrophilic) than their neopentyl analogues. The metabolism of selected TFNP ethers was explored in the fungus Cunninghamella elegans. (AU)

• Processo FAPESP: 22/10156-7 - Estudo experimental e teórico dos efeitos estereoeletrônicos e arranjo supramolecular de compostos organofluorados
• Beneficiário: Bruno de Almeida Piscelli
• Modalidade de apoio: Bolsas no Brasil - Doutorado Direto
• Processo FAPESP: 23/14064-2 - Modelagem da interação de ciclohexanos Janus-face com dsDNA e ssDNA.
• Beneficiário: Bruno de Almeida Piscelli
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Doutorado Direto
• Processo FAPESP: 18/03910-1 - Estudos físico-químicos de compostos orgânicos fluorados: abordagens experimental e teórica
• Beneficiário: Rodrigo Antonio Cormanich
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores