Reactions of CF3-enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands

4-Aryl-1,1,1-trifluorobut-3-en-2-ones ArCH[double bond, length as m-dash]CHCOCF3 (CF3-enones) react with arenes in excess of Brønsted superacids (TfOH, FSO3H) to give, stereoselectively, trans-1,3-diaryl-1-trifluoromethyl indanes in 35-85% yields. The reaction intermediates, the O-protonated ArCH[double bond, length as m-dash]CHC(OH(+))CF3 and the O,C-diprotonated ArHC(+)CH2C(OH(+))CF3 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 CF3-indanes is a result of cascade reaction of protonated CF3-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 CB1 and CB2 types. The most potent compound showed sub-micromolar affinity for both receptor subtypes with a 6-fold selectivity toward the CB2 receptor with no appreciable cytotoxicity toward SHSY5Y cells.

Die beiden letzten Meetings in der Royal Asiatic Society in London : nach dem Jews Chronicle

Meir ben David ha-Kohen Wiener

Parallelen aus der jüdischen Geschichte : Vortrag gehalten in London den 16. Juni für die englisch-jüdische historische Ausstellung im Saale des Royal Albert Hall

Heinrich Graetz

The rose of Castille : opera in three acts ; ... and performed in the presence of Her Majesty and the Court (by Royal command) on the occasion of the festival performances at Her Majesty's Theatre, in honor of the nuptials of The Princess Royal and The Prince of Prussia, January 21, 1858

the music (composed expressly for the Pyne and Harrison English opera Company) by M. W. Balfe. [Text] by A. Harris and E. Falconer

The songs, duetts, choruses, & c. in Fair Rosamond : a grand opera, in four acts ; performed, for the first time, at the Theatre Royal, Drury Lane, February 28th, 1837

the overture, and the whole of the music, by John Barnett

Fidelio : or, constancy rewarded! ; an opera, in three acts, as performed at the Theatre Royal, Drury-Lane, by the author of the "Freyschutz", "The eagle's haunt" &c

[Ludwig van Beethoven]

Geschichte von Port-Royal : der Kampf des reformirten und des jesuitischen Katholicismus unter Louis XIII und XIV

Hermann Reuchlin

Léon Ponzio als Kunrad, Rollenbild, Brustbild, in: Richard Strauss: Feuersnot, Théatre Royal de la Monnaie

Signatur des Originals: S 36/F05816

Léon Ponzio als Kunrad, Rollenbild, Brustbild, in: Richard Strauss: Feuersnot, Théatre Royal de la Monnaie

Signatur des Originals: S 36/F05817

Théâtre Royal de la Monnaie, L'Opéra de Frankfort-sur-le-Main, Les Noces de Figaro

Signatur des Originals: S 36/F07909

Chollet du Théâtre royal de l'Opéra Comique.

Signatur des Originals: S 36/G00628

Eduard Eliason, Chef de l'Orchestre du Theatre Royal Drury Lane à Londres

Signatur des Originals: S 36/G00781

View of the Gallery prepared for the reception of their Majesties, the Royal Family, Directors, & principal Personage in the Kingdom, at the Commemoration of Handel in Westminster Abbey

Signatur des Originals: S 36/G02676