150892-04-9Relevant academic research and scientific papers
Synthesis and evaluation of chiral β-amino acid-based low-molecular-weight organogelators possessing a methyl/trifluoromethyl side chain
Kodama, Koichi,Kawamata, Ryuta,Hirose, Takuji
supporting information, p. 2882 - 2887 (2019/02/17)
The synthesis and gelation properties of chiral β-amino acid-based low-molecular-weight organogelators, possessing methyl/trifluoromethyl side chains, are reported. The structure of the side chain and chirality were found to be important parameters affecting the gelation ability. The pure enantiomer of the trifluoromethylated β-amino acid displayed good gelation properties due to the formation of fibrillar networks, driven by enhanced amide hydrogen bonding. An investigation of the effects of the alkyl chain length showed that longer alkyl chain improved the gelation ability, yet the same supramolecular structure was observed in all, as well as an odd-even effect in both the melting points and Tg values.
Synthesis of 1-alkyl-2-(trifluoromethyl)azetidines and their regiospecific ring opening toward diverse α-(trifluoromethyl)amines via intermediate azetidinium salts
Kenis, Sara,D'Hooghe, Matthias,Verniest, Guido,Dang Thi, Tuyet Anh,Pham The, Chinh,Van Nguyen, Tuyen,De Kimpe, Norbert
experimental part, p. 5982 - 5992 (2012/09/21)
A convenient approach toward nonactivated 1-alkyl-2-(trifluoromethyl) azetidines as a new class of constrained azaheterocycles was developed starting from ethyl 4,4,4-trifluoroacetoacetate via imination, hydride reduction, chlorination, and base-induced ring closure. Furthermore, the reactivity profile of these 2-CF3-azetidines was assessed by means of quaternization and subsequent regiospecific ring opening at C4 of the azetidinium intermediates by oxygen, nitrogen, carbon, sulfur, and halogen nucleophiles, pointing to a clear difference in reactivity compared to azetidines bearing other types of electron-withdrawing groups at C2.
