CCDC no.: 1569702The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.
Source of materialsThe title compound was synthesized by Aldol condensation between two molecules of 2-(trifluoromethyl)benzaldehyde and cyclopentanone, which was synthesized according our earlier published method [1,2]. In detail: 5.0 mmol cyclopentanone was added to a solution of 10 mmol 2-(trifluoromethyl)benzaldehyde in MeOH (10 mL). The solution was stirred at room temperature for 30 min, followed by dropwise addition of NaOCH 3 /CH 3 OH (1.0 mL, 5.0 mmol). The mixture was stirred at room temperature and monitored with TLC. When the reaction was finished, the residue was poured into saturated NH 4 Cl solution and filtered. The precipitate was washed with water and cold ethanol, and dried in vacuum. The solid was further purified by silica gel chromatography (CH 2 Cl 2 /CH 3 OH). All chemicals used for the synthesis were commercially available and were used without further purification. The yellow crystals of the title compound were obtained by slow evaporation of a CH 3 OH solution at room temperature.
Experimental detailsPosition of the H atoms were calculated based on geometric criteria (C-H = 0.97 and 0.93 for methyl and aromatic atoms, respectively) and placed in their calculated position and refined, using a riding model with U iso (H) = 1.5 U eq (C) for methyl and U iso (H) = 1.2 U eq (C) for all others.
DiscussionCurcumin has been demonstrated to possess a wide range of pharmaceutical activities, such as anti-tumor [3,4], antiinflammation [5], anti-oxidation [6], anti-bacterial [7], and cardiovascular protection [8,9]. However, its high metabolic instability and low bioavailability have dramatically limited its practical application [10]. Recently, our research group has synthesized a series of mono-carbonyl analogs of curcumin (MACs) by deleting β-diketone moiety [11,12]. The title compound is an Curcumin analogon with one central keto group only.