(E)-1-(2-Aminophenyl)-3- (benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one

Abonia, Rodrigo and Arteaga, Diana and Insuasty, Daniel and Quiroga, Jairo and Insuasty, Braulio and Moreno-Fuquen, Rodolfo and Kennedy, Alan R. (2016) (E)-1-(2-Aminophenyl)-3- (benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one. Molbank, 2017 (1). M924. ISSN 1422-8599 (https://doi.org/10.3390/M924)

[thumbnail of Abonia-etal-Molbank2016-(E)-1-(2-Aminophenyl)-3- (benzo[d][1,3]dioxol-5-yl)]
Text. Filename: Abonia_etal_Molbank2016_E_1_2_Aminophenyl_3_benzo_d_1_3_dioxol_5_yl_.pdf
Final Published Version
License: Creative Commons Attribution 4.0 logo

Download (1MB)| Preview


The title chalcone (E)-1-(2-aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one was obtained in 76% yield from a NaOH catalyzed Claisen–Schmidt condensation reaction between o-aminoacetophenone and piperonal. This product will be used as a key precursor for the development of an alternative route for the total synthesis of the alkaloid Graveoline. Single crystals of the title compound suitable for X-ray diffraction were grown via slow evaporation in ethanol at room temperature. A complete crystallographic study was performed in depth to unequivocally confirm its structure. The crystal structure of the title o-aminochalcone, C16H13NO3, shows two molecules per asymmetric unit (Z = 4) and adopts an E configuration about the C=C double bond. In the title compound, the mean plane of the non-H atoms of the central chalcone fragment C—C(O)—C—C—C is as follow: [root-mean-square (r.m.s.) deviation = 0.0210 Å for A–B and 0.0493 for C–D molecules]. In the crystal, molecules are linked by N–H...O and C–H...O, hydrogen bonds forming S(6), R22(6) and edge-fused R44(24)rings along with C(18) chains running parallel to (110).