1‐(4‐Aminophenoxy)‐3‐(alkyl)propane‐2‐ols as Building Blocks for the Preparation of Membranogenic Compounds

This study explores the potential use of 1‐(4‐aminophenoxy)‐3‐(alkyl)propane‐2‐ol (anilines, 4 ) as building blocks for the preparation of membranogenic compounds. Anilines were synthesized via linear and convergent methods with good to high yields (39%–99%). Key intermediates, 1‐(alkyloxy)‐3‐(4‐nitrophenoxy)propan‐2‐ols ( 3 ), were obtained by reacting 2‐(alkoxymethyl)oxirane ( 2 ) or 2‐((4‐nitrophenoxy)methyl)oxirane ( 7 ) with p ‐nitrophenol or an alcohol, respectively. Three reduction methods were employed to achieve the final anilines. Following chain‐length screening, octyl and geranyl derivatives were selected to prepare lyso‐phospholipid ether analogues. These compounds were then evaluated for their self‐assembly properties in forming giant unilamellar vesicles using either phase transfer or electro‐formation methodology.