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

Rodrigo Abonia, Diana Arteaga, Daniel Insuasty, Jairo Quiroga, Braulio Insuasty, Rodolfo Moreno-Fuquen, Alan R. Kennedy

Research output: Contribution to journalArticle

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Abstract

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).
Original languageEnglish
Article numberM924
Number of pages6
JournalMolbank
Volume2017
Issue number1
DOIs
Publication statusPublished - 30 Dec 2016

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Chalcone
Molecules
Alkaloids
X-Ray Diffraction
molecules
Hydrogen
alkaloids
Ethanol
Condensation reactions
Temperature
Hydrogen bonds
Evaporation
ethyl alcohol
condensation
Crystal structure
routes
fragments
evaporation
Single crystals
methylidyne

Keywords

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

Cite this

Abonia, R., Arteaga, D., Insuasty, D., Quiroga, J., Insuasty, B., Moreno-Fuquen, R., & Kennedy, A. R. (2016). (E)-1-(2-Aminophenyl)-3- (benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one. Molbank, 2017(1), [M924]. https://doi.org/10.3390/M924
Abonia, Rodrigo ; Arteaga, Diana ; Insuasty, Daniel ; Quiroga, Jairo ; Insuasty, Braulio ; Moreno-Fuquen, Rodolfo ; Kennedy, Alan R. / (E)-1-(2-Aminophenyl)-3- (benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one. In: Molbank. 2016 ; Vol. 2017, No. 1.
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abstract = "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 {\AA} 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).",
keywords = "o-aminoacetophenones, benzodioxolyl moiety, Claisen–Schmidt condensation, o-aminochalcones, single crystal X-ray diffraction",
author = "Rodrigo Abonia and Diana Arteaga and Daniel Insuasty and Jairo Quiroga and Braulio Insuasty and Rodolfo Moreno-Fuquen and Kennedy, {Alan R.}",
year = "2016",
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Abonia, R, Arteaga, D, Insuasty, D, Quiroga, J, Insuasty, B, Moreno-Fuquen, R & Kennedy, AR 2016, '(E)-1-(2-Aminophenyl)-3- (benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one', Molbank, vol. 2017, no. 1, M924. https://doi.org/10.3390/M924

(E)-1-(2-Aminophenyl)-3- (benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one. / Abonia, Rodrigo; Arteaga, Diana; Insuasty, Daniel; Quiroga, Jairo; Insuasty, Braulio; Moreno-Fuquen, Rodolfo; Kennedy, Alan R.

In: Molbank, Vol. 2017, No. 1, M924, 30.12.2016.

Research output: Contribution to journalArticle

TY - JOUR

T1 - (E)-1-(2-Aminophenyl)-3- (benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one

AU - Abonia, Rodrigo

AU - Arteaga, Diana

AU - Insuasty, Daniel

AU - Quiroga, Jairo

AU - Insuasty, Braulio

AU - Moreno-Fuquen, Rodolfo

AU - Kennedy, Alan R.

PY - 2016/12/30

Y1 - 2016/12/30

N2 - 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).

AB - 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).

KW - o-aminoacetophenones

KW - benzodioxolyl moiety

KW - Claisen–Schmidt condensation

KW - o-aminochalcones

KW - single crystal X-ray diffraction

UR - http://www.mdpi.com/journal/molbank

U2 - 10.3390/M924

DO - 10.3390/M924

M3 - Article

VL - 2017

JO - Molbank

JF - Molbank

SN - 1422-8599

IS - 1

M1 - M924

ER -

Abonia R, Arteaga D, Insuasty D, Quiroga J, Insuasty B, Moreno-Fuquen R et al. (E)-1-(2-Aminophenyl)-3- (benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one. Molbank. 2016 Dec 30;2017(1). M924. https://doi.org/10.3390/M924