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(1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hydroxy-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0(2,7).0(15,20)]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate
The title compound, C(40)H(41)NO(8), is a product of the reduction of the cyclic carbonyl group of the γ-piperidone subunit of the aza-14-crown-4 ether with subsequent re-esterification of its dimethyl butenoate substituent into a monoethyl monomethyl group. The azacrown macrocycle exhibits a bowl...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3772461/ https://www.ncbi.nlm.nih.gov/pubmed/24046604 http://dx.doi.org/10.1107/S1600536813014748 |
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author | Hieu, Truong Hong Anh, Le Tuan Soldatenkov, Anatoly T. Gorchakova, Olga S. Khrustalev, Victor N. |
author_facet | Hieu, Truong Hong Anh, Le Tuan Soldatenkov, Anatoly T. Gorchakova, Olga S. Khrustalev, Victor N. |
author_sort | Hieu, Truong Hong |
collection | PubMed |
description | The title compound, C(40)H(41)NO(8), is a product of the reduction of the cyclic carbonyl group of the γ-piperidone subunit of the aza-14-crown-4 ether with subsequent re-esterification of its dimethyl butenoate substituent into a monoethyl monomethyl group. The azacrown macrocycle exhibits a bowl conformation with a dihedral angle of 70.82 (5)° between the benzene rings fused to it. The piperidine ring adopts a chair conformation and the methyl ethyl ethylenedicarboxylate fragment has a cis conformation, with a dihedral angle of 66.51 (7)° between the two carboxylate groups. The ethyl group is disordered over two sites with occupancies of 0.70 (1):0.30 (1). In the crystal, molecules form inversion dimers, via pairs of O—H⋯O hydrogen bonds, that stack along the a axis. |
format | Online Article Text |
id | pubmed-3772461 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-37724612013-09-17 (1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hydroxy-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0(2,7).0(15,20)]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate Hieu, Truong Hong Anh, Le Tuan Soldatenkov, Anatoly T. Gorchakova, Olga S. Khrustalev, Victor N. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(40)H(41)NO(8), is a product of the reduction of the cyclic carbonyl group of the γ-piperidone subunit of the aza-14-crown-4 ether with subsequent re-esterification of its dimethyl butenoate substituent into a monoethyl monomethyl group. The azacrown macrocycle exhibits a bowl conformation with a dihedral angle of 70.82 (5)° between the benzene rings fused to it. The piperidine ring adopts a chair conformation and the methyl ethyl ethylenedicarboxylate fragment has a cis conformation, with a dihedral angle of 66.51 (7)° between the two carboxylate groups. The ethyl group is disordered over two sites with occupancies of 0.70 (1):0.30 (1). In the crystal, molecules form inversion dimers, via pairs of O—H⋯O hydrogen bonds, that stack along the a axis. International Union of Crystallography 2013-06-08 /pmc/articles/PMC3772461/ /pubmed/24046604 http://dx.doi.org/10.1107/S1600536813014748 Text en © Hieu et al. 2013 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 Hieu, Truong Hong Anh, Le Tuan Soldatenkov, Anatoly T. Gorchakova, Olga S. Khrustalev, Victor N. (1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hydroxy-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0(2,7).0(15,20)]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate |
title | (1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hydroxy-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0(2,7).0(15,20)]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate |
title_full | (1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hydroxy-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0(2,7).0(15,20)]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate |
title_fullStr | (1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hydroxy-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0(2,7).0(15,20)]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate |
title_full_unstemmed | (1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hydroxy-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0(2,7).0(15,20)]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate |
title_short | (1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hydroxy-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0(2,7).0(15,20)]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate |
title_sort | (1r*,21s*,22r*,24s*)-methyl ethyl 2-[23-hydroxy-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0(2,7).0(15,20)]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3772461/ https://www.ncbi.nlm.nih.gov/pubmed/24046604 http://dx.doi.org/10.1107/S1600536813014748 |
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