(E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one
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 rou...
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| Format: | Article |
| Language: | English |
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MDPI AG
2016-12-01
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| Series: | Molbank |
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| Online Access: | http://www.mdpi.com/1422-8599/2017/1/M924 |
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| author | Rodrigo Abonia Diana Arteaga Daniel Insuasty Jairo Quiroga Braulio Insuasty Rodolfo Moreno-Fuquen Alan R. Kennedy |
| author_facet | Rodrigo Abonia Diana Arteaga Daniel Insuasty Jairo Quiroga Braulio Insuasty Rodolfo Moreno-Fuquen Alan R. Kennedy |
| author_sort | Rodrigo Abonia |
| collection | DOAJ |
| description | 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). |
| first_indexed | 2024-12-19T07:40:02Z |
| format | Article |
| id | doaj.art-0af9dd604eb44751b29c5ba55291c98f |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-12-19T07:40:02Z |
| publishDate | 2016-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-0af9dd604eb44751b29c5ba55291c98f2022-12-21T20:30:28ZengMDPI AGMolbank1422-85992016-12-0120171M92410.3390/M924M924(E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-oneRodrigo Abonia0Diana Arteaga1Daniel Insuasty2Jairo Quiroga3Braulio Insuasty4Rodolfo Moreno-Fuquen5Alan R. Kennedy6Department of Chemistry, Universidad del Valle, A.A. 25360 Santiago de Cali, ColombiaDepartment of Chemistry, Universidad del Valle, A.A. 25360 Santiago de Cali, ColombiaDepartment of Chemistry, Universidad del Valle, A.A. 25360 Santiago de Cali, ColombiaDepartment of Chemistry, Universidad del Valle, A.A. 25360 Santiago de Cali, ColombiaDepartment of Chemistry, Universidad del Valle, A.A. 25360 Santiago de Cali, ColombiaDepartment of Chemistry, Universidad del Valle, A.A. 25360 Santiago de Cali, ColombiaWestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, ScotlandThe 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).http://www.mdpi.com/1422-8599/2017/1/M924o-aminoacetophenonesbenzodioxolyl moietyClaisen–Schmidt condensationo-aminochalconessingle crystal X-ray diffraction |
| spellingShingle | Rodrigo Abonia Diana Arteaga Daniel Insuasty Jairo Quiroga Braulio Insuasty Rodolfo Moreno-Fuquen Alan R. Kennedy (E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one Molbank o-aminoacetophenones benzodioxolyl moiety Claisen–Schmidt condensation o-aminochalcones single crystal X-ray diffraction |
| title | (E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one |
| title_full | (E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one |
| title_fullStr | (E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one |
| title_full_unstemmed | (E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one |
| title_short | (E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one |
| title_sort | e 1 2 aminophenyl 3 benzo d 1 3 dioxol 5 yl prop 2 en 1 one |
| topic | o-aminoacetophenones benzodioxolyl moiety Claisen–Schmidt condensation o-aminochalcones single crystal X-ray diffraction |
| url | http://www.mdpi.com/1422-8599/2017/1/M924 |
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