Cargando…
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...
Autores principales: | , , , , |
---|---|
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 |
_version_ | 1782191458398240768 |
---|---|
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. |
format | Text |
id | pubmed-2979627 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT kimmelroman 3ethyl8methoxy42346tetraoacetylbdglucopyranosyloxyquinolin21hone AT necasmarek 3ethyl8methoxy42346tetraoacetylbdglucopyranosyloxyquinolin21hone AT kafkastanislav 3ethyl8methoxy42346tetraoacetylbdglucopyranosyloxyquinolin21hone AT kosmrljjanez 3ethyl8methoxy42346tetraoacetylbdglucopyranosyloxyquinolin21hone AT vicharobert 3ethyl8methoxy42346tetraoacetylbdglucopyranosyloxyquinolin21hone |