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3,5-Bis(ethoxy­carbon­yl)-2,6-dimethyl-1,4-dihydro­pyridine-4-carboxylic acid

The title mol­ecule, C(14)H(19)NO(6), was synthesized by the reaction of glyoxylic acid, ethyl acetoacetate and NH(4)HCO(3). In the crystal structure, the dihydro­pyridine ring adopts an asymmetric boat-type conformation with the C atom bearing the carboxyl group showing a signficantly larger deviat...

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Detalles Bibliográficos
Autores principales: Wu, De-Hong, Hu, Ling
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977273/
https://www.ncbi.nlm.nih.gov/pubmed/21583459
http://dx.doi.org/10.1107/S1600536809024945
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author Wu, De-Hong
Hu, Ling
author_facet Wu, De-Hong
Hu, Ling
author_sort Wu, De-Hong
collection PubMed
description The title mol­ecule, C(14)H(19)NO(6), was synthesized by the reaction of glyoxylic acid, ethyl acetoacetate and NH(4)HCO(3). In the crystal structure, the dihydro­pyridine ring adopts an asymmetric boat-type conformation with the C atom bearing the carboxyl group showing a signficantly larger deviation [0.325 (2) Å] from the base plane then the N atom [0.137 (2) Å]. One of the ethyl groups is disordered over two positions with occupancies of 0.741 (10) and 0.259 (10). The crystal is stabilized by strong inter­molecular hydrogen bonds. N—H⋯O inter­actions form infinite chains in the a direction. O—H⋯O hydrogen bonds form typical carboxylic acid dimers, which link the N—H⋯O chains into a ladder-type double chain.
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spelling pubmed-29772732010-12-30 3,5-Bis(ethoxy­carbon­yl)-2,6-dimethyl-1,4-dihydro­pyridine-4-carboxylic acid Wu, De-Hong Hu, Ling Acta Crystallogr Sect E Struct Rep Online Organic Papers The title mol­ecule, C(14)H(19)NO(6), was synthesized by the reaction of glyoxylic acid, ethyl acetoacetate and NH(4)HCO(3). In the crystal structure, the dihydro­pyridine ring adopts an asymmetric boat-type conformation with the C atom bearing the carboxyl group showing a signficantly larger deviation [0.325 (2) Å] from the base plane then the N atom [0.137 (2) Å]. One of the ethyl groups is disordered over two positions with occupancies of 0.741 (10) and 0.259 (10). The crystal is stabilized by strong inter­molecular hydrogen bonds. N—H⋯O inter­actions form infinite chains in the a direction. O—H⋯O hydrogen bonds form typical carboxylic acid dimers, which link the N—H⋯O chains into a ladder-type double chain. International Union of Crystallography 2009-07-04 /pmc/articles/PMC2977273/ /pubmed/21583459 http://dx.doi.org/10.1107/S1600536809024945 Text en © Wu and Hu 2009 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Wu, De-Hong
Hu, Ling
3,5-Bis(ethoxy­carbon­yl)-2,6-dimethyl-1,4-dihydro­pyridine-4-carboxylic acid
title 3,5-Bis(ethoxy­carbon­yl)-2,6-dimethyl-1,4-dihydro­pyridine-4-carboxylic acid
title_full 3,5-Bis(ethoxy­carbon­yl)-2,6-dimethyl-1,4-dihydro­pyridine-4-carboxylic acid
title_fullStr 3,5-Bis(ethoxy­carbon­yl)-2,6-dimethyl-1,4-dihydro­pyridine-4-carboxylic acid
title_full_unstemmed 3,5-Bis(ethoxy­carbon­yl)-2,6-dimethyl-1,4-dihydro­pyridine-4-carboxylic acid
title_short 3,5-Bis(ethoxy­carbon­yl)-2,6-dimethyl-1,4-dihydro­pyridine-4-carboxylic acid
title_sort 3,5-bis(ethoxy­carbon­yl)-2,6-dimethyl-1,4-dihydro­pyridine-4-carboxylic acid
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977273/
https://www.ncbi.nlm.nih.gov/pubmed/21583459
http://dx.doi.org/10.1107/S1600536809024945
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