AbstractThe 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). View Full-Text
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Abonia, R.; Arteaga, D.; Insuasty, D.; Quiroga, J.; Insuasty, B.; Moreno-Fuquen, R.; Kennedy, A.R. (E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one. Molbank 2017, 2017, M924.
Abonia R, Arteaga D, Insuasty D, Quiroga J, Insuasty B, Moreno-Fuquen R, Kennedy AR. (E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one. Molbank. 2017; 2017(1):M924.Chicago/Turabian Style
Abonia, Rodrigo; Arteaga, Diana; Insuasty, Daniel; Quiroga, Jairo; Insuasty, Braulio; Moreno-Fuquen, Rodolfo; Kennedy, Alan R. 2017. "(E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one." Molbank 2017, no. 1: M924.
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