Details

Autor(en) / Beteiligte

• Iakovenko, Roman O.
• Kazakova, Anna N.
• Muzalevskiy, Vasiliy M.
• Ivanov, Alexander Yu
• Boyarskaya, Irina A.
• Chicca, Andrea
• Petrucci, Vanessa
• Gertsch, Jürg
• Krasavin, Mikhail
• Starova, Galina L.
• Zolotarev, Andrey A.
• Avdontceva, Margarita S.
• Nenajdenko, Valentine G.
• Vasilyev, Aleksander V.

Titel

Reactions of CF 3 -enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF 3 -indanes, new cannabinoid receptor ligands

Ist Teil von

• Organic & biomolecular chemistry, 2015, Vol.13 (33), p.8827-8842

Erscheinungsjahr

2015

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 4-Aryl-1,1,1-trifluorobut-3-en-2-ones ArCHCHCOCF 3 (CF 3 -enones) react with arenes in excess of Brønsted superacids (TfOH, FSO 3 H) to give, stereoselectively, trans -1,3-diaryl-1-trifluoromethyl indanes in 35–85% yields. The reaction intermediates, the O-protonated ArCHCHC(OH + )CF 3 and the O,C-diprotonated ArHC + CH 2 C(OH + )CF 3 species, have been studied by means of 1 H, 13 C, 19 F NMR, and DFT calculations. Both types of the cations may participate in the reaction, depending on their electrophilicity and electron-donating properties of the arenes. The formation of CF 3 -indanes is a result of cascade reaction of protonated CF 3 -enones to form chemo-, regio- and stereoselectively three new C–C bonds. The obtained trans -1,3-diaryl-1-trifluoromethyl indanes were investigated as potential ligands for cannabinoid receptors CB 1 and CB 2 types. The most potent compound showed sub-micromolar affinity for both receptor subtypes with a 6-fold selectivity toward the CB 2 receptor with no appreciable cytotoxicity toward SHSY5Y cells.