(E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one

Rodrigo Abonia, Lorena Cabrera, Jairo Quiroga, Braulio Insuasty, Rodolfo Moreno-Fuquen, Alan R. Kennedy

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Abstract

The title chalcone (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one was prepared with an excellent yield from a Claisen–Schmidt condensation reaction between o-aminoacetophenone and p-chlorobenzaldehyde. This product will be used as a key precursor for the development of an alternative route for the total synthesis of dubamine and graveoline alkaloids. 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 and determine some interesting supramolecular properties. The crystal structure of the title o-aminochalcone, C15H12ClNO, shows two molecules per asymmetric unit (Z′ = 2) 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 follows: [r.m.s. deviation = 0.0130 Å for A-B and 0.0043 for C-D molecules]. In the crystal, molecules are linked by N—H...N and C—H...O, hydrogen bonds forming edge-fused R66(46) rings parallel to (100). Additionally, N—H...O hydrogen bonds generate a three-dimensional network.
Original languageEnglish
Article numberM911
Number of pages6
JournalMolbank
Volume2016
Issue number4
DOIs
Publication statusPublished - 15 Oct 2016

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Keywords

  • o-aminoacetophenones
  • Claisen–Schmidt condensation
  • o-aminochalcones
  • single crystal X-ray diffraction

Cite this

Abonia, R., Cabrera, L., Quiroga, J., Insuasty, B., Moreno-Fuquen, R., & Kennedy, A. R. (2016). (E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one. Molbank, 2016(4), [M911]. https://doi.org/10.3390/M911