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3-Ethyl-8-meth­oxy-4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranos­yloxy)quinolin-2(1H)-one

The structure of the title compound, C(26)H(31)NO(12), contains an essentially planar quinoline skeleton, with the maximum deviation from the best plane being 0.055 (2) Å, and an oxane ring in a classical chair conformation with the following Cremer and Pople puckering parameters: Q = 0.586 (2) Å, θ...

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Autores principales: Kimmel, Roman, Nečas, Marek, Kafka, Stanislav, Košmrlj, Janez, Vícha, Robert
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979627/
https://www.ncbi.nlm.nih.gov/pubmed/21579419
http://dx.doi.org/10.1107/S1600536810016636
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author Kimmel, Roman
Nečas, Marek
Kafka, Stanislav
Košmrlj, Janez
Vícha, Robert
author_facet Kimmel, Roman
Nečas, Marek
Kafka, Stanislav
Košmrlj, Janez
Vícha, Robert
author_sort Kimmel, Roman
collection PubMed
description The structure of the title compound, C(26)H(31)NO(12), contains an essentially planar quinoline skeleton, with the maximum deviation from the best plane being 0.055 (2) Å, and an oxane ring in a classical chair conformation with the following Cremer and Pople puckering parameters: Q = 0.586 (2) Å, θ = 11.5 (2)° and ϕ = 309.4 (10)°. One acetyl group displays rotational disorder with occupancies of 0.634 (8):0.366 (8). The crystal packing is stabilized by N—H⋯O hydrogen bonds, which link mol­ecules into chains along the a axis. The packing is further stabilized by weak C—H⋯O interactions. The absolute configurations on the carbons in the oxane ring correspond to those of the commercial starting material and are unchanged in the well known mechanism of the Koenigs–Knorr synthesis.
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spelling pubmed-29796272010-12-30 3-Ethyl-8-meth­oxy-4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranos­yloxy)quinolin-2(1H)-one Kimmel, Roman Nečas, Marek Kafka, Stanislav Košmrlj, Janez Vícha, Robert Acta Crystallogr Sect E Struct Rep Online Organic Papers The structure of the title compound, C(26)H(31)NO(12), contains an essentially planar quinoline skeleton, with the maximum deviation from the best plane being 0.055 (2) Å, and an oxane ring in a classical chair conformation with the following Cremer and Pople puckering parameters: Q = 0.586 (2) Å, θ = 11.5 (2)° and ϕ = 309.4 (10)°. One acetyl group displays rotational disorder with occupancies of 0.634 (8):0.366 (8). The crystal packing is stabilized by N—H⋯O hydrogen bonds, which link mol­ecules into chains along the a axis. The packing is further stabilized by weak C—H⋯O interactions. The absolute configurations on the carbons in the oxane ring correspond to those of the commercial starting material and are unchanged in the well known mechanism of the Koenigs–Knorr synthesis. International Union of Crystallography 2010-05-12 /pmc/articles/PMC2979627/ /pubmed/21579419 http://dx.doi.org/10.1107/S1600536810016636 Text en © Kimmel et al. 2010 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
Kimmel, Roman
Nečas, Marek
Kafka, Stanislav
Košmrlj, Janez
Vícha, Robert
3-Ethyl-8-meth­oxy-4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranos­yloxy)quinolin-2(1H)-one
title 3-Ethyl-8-meth­oxy-4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranos­yloxy)quinolin-2(1H)-one
title_full 3-Ethyl-8-meth­oxy-4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranos­yloxy)quinolin-2(1H)-one
title_fullStr 3-Ethyl-8-meth­oxy-4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranos­yloxy)quinolin-2(1H)-one
title_full_unstemmed 3-Ethyl-8-meth­oxy-4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranos­yloxy)quinolin-2(1H)-one
title_short 3-Ethyl-8-meth­oxy-4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranos­yloxy)quinolin-2(1H)-one
title_sort 3-ethyl-8-meth­oxy-4-(2,3,4,6-tetra-o-acetyl-β-d-glucopyranos­yloxy)quinolin-2(1h)-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979627/
https://www.ncbi.nlm.nih.gov/pubmed/21579419
http://dx.doi.org/10.1107/S1600536810016636
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