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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...

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Autores principales: Hieu, Truong Hong, Anh, Le Tuan, Soldatenkov, Anatoly T., Gorchakova, Olga S., Khrustalev, Victor N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
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.
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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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