Cargando…
Methyl (9aR*,10S*,11R*,13aS*,13bS*)-9-oxo-6,7,9,9a,10,11-hexahydro-5H,13bH-11,13a-epoxypyrrolo[2′,1′:3,4][1,4]diazepino[2,1-a]isoindole-10-carboxylate
The title compound, C(17)H(18)N(2)O(4), is the methyl ester of the adduct of intramolecular Diels–Alder reaction between maleic anhydride and 1-(2-furyl)-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine. The molecule comprises a fused pentacyclic system containing four five-membered rings (v...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247590/ https://www.ncbi.nlm.nih.gov/pubmed/22219895 http://dx.doi.org/10.1107/S1600536811040360 |
_version_ | 1782220142062600192 |
---|---|
author | Toze, Flavien A. A. Airiyan, Inga K. Nikitina, Eugeniya V. Sorokina, Elena A. Khrustalev, Victor N. |
author_facet | Toze, Flavien A. A. Airiyan, Inga K. Nikitina, Eugeniya V. Sorokina, Elena A. Khrustalev, Victor N. |
author_sort | Toze, Flavien A. A. |
collection | PubMed |
description | The title compound, C(17)H(18)N(2)O(4), is the methyl ester of the adduct of intramolecular Diels–Alder reaction between maleic anhydride and 1-(2-furyl)-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine. The molecule comprises a fused pentacyclic system containing four five-membered rings (viz. pyrrole, 2-pyrrolidinone, tetrahydrofuran and dihydrofuran) and one seven-membered ring (1,4-diazepane). The pyrrole ring is approximately planar (r.m.s. deviation = 0.003 Å) while the 2-pyrrolidinone, tetrahydrofuran and dihydrofuran five-membered rings have the usual envelope conformations. The central seven-membered diazepane ring adopts a boat conformation. In the crystal, molecules are bound by weak intermolecular C—H⋯O hydrogen-bonding interactions into zigzag chains propagating in [010]. In the crystal packing, the chains are stacked along the a axis. |
format | Online Article Text |
id | pubmed-3247590 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32475902012-01-04 Methyl (9aR*,10S*,11R*,13aS*,13bS*)-9-oxo-6,7,9,9a,10,11-hexahydro-5H,13bH-11,13a-epoxypyrrolo[2′,1′:3,4][1,4]diazepino[2,1-a]isoindole-10-carboxylate Toze, Flavien A. A. Airiyan, Inga K. Nikitina, Eugeniya V. Sorokina, Elena A. Khrustalev, Victor N. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(17)H(18)N(2)O(4), is the methyl ester of the adduct of intramolecular Diels–Alder reaction between maleic anhydride and 1-(2-furyl)-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine. The molecule comprises a fused pentacyclic system containing four five-membered rings (viz. pyrrole, 2-pyrrolidinone, tetrahydrofuran and dihydrofuran) and one seven-membered ring (1,4-diazepane). The pyrrole ring is approximately planar (r.m.s. deviation = 0.003 Å) while the 2-pyrrolidinone, tetrahydrofuran and dihydrofuran five-membered rings have the usual envelope conformations. The central seven-membered diazepane ring adopts a boat conformation. In the crystal, molecules are bound by weak intermolecular C—H⋯O hydrogen-bonding interactions into zigzag chains propagating in [010]. In the crystal packing, the chains are stacked along the a axis. International Union of Crystallography 2011-10-05 /pmc/articles/PMC3247590/ /pubmed/22219895 http://dx.doi.org/10.1107/S1600536811040360 Text en © Toze et al. 2011 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 Toze, Flavien A. A. Airiyan, Inga K. Nikitina, Eugeniya V. Sorokina, Elena A. Khrustalev, Victor N. Methyl (9aR*,10S*,11R*,13aS*,13bS*)-9-oxo-6,7,9,9a,10,11-hexahydro-5H,13bH-11,13a-epoxypyrrolo[2′,1′:3,4][1,4]diazepino[2,1-a]isoindole-10-carboxylate |
title | Methyl (9aR*,10S*,11R*,13aS*,13bS*)-9-oxo-6,7,9,9a,10,11-hexahydro-5H,13bH-11,13a-epoxypyrrolo[2′,1′:3,4][1,4]diazepino[2,1-a]isoindole-10-carboxylate |
title_full | Methyl (9aR*,10S*,11R*,13aS*,13bS*)-9-oxo-6,7,9,9a,10,11-hexahydro-5H,13bH-11,13a-epoxypyrrolo[2′,1′:3,4][1,4]diazepino[2,1-a]isoindole-10-carboxylate |
title_fullStr | Methyl (9aR*,10S*,11R*,13aS*,13bS*)-9-oxo-6,7,9,9a,10,11-hexahydro-5H,13bH-11,13a-epoxypyrrolo[2′,1′:3,4][1,4]diazepino[2,1-a]isoindole-10-carboxylate |
title_full_unstemmed | Methyl (9aR*,10S*,11R*,13aS*,13bS*)-9-oxo-6,7,9,9a,10,11-hexahydro-5H,13bH-11,13a-epoxypyrrolo[2′,1′:3,4][1,4]diazepino[2,1-a]isoindole-10-carboxylate |
title_short | Methyl (9aR*,10S*,11R*,13aS*,13bS*)-9-oxo-6,7,9,9a,10,11-hexahydro-5H,13bH-11,13a-epoxypyrrolo[2′,1′:3,4][1,4]diazepino[2,1-a]isoindole-10-carboxylate |
title_sort | methyl (9ar*,10s*,11r*,13as*,13bs*)-9-oxo-6,7,9,9a,10,11-hexahydro-5h,13bh-11,13a-epoxypyrrolo[2′,1′:3,4][1,4]diazepino[2,1-a]isoindole-10-carboxylate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247590/ https://www.ncbi.nlm.nih.gov/pubmed/22219895 http://dx.doi.org/10.1107/S1600536811040360 |
work_keys_str_mv | AT tozeflavienaa methyl9ar10s11r13as13bs9oxo6799a1011hexahydro5h13bh1113aepoxypyrrolo213414diazepino21aisoindole10carboxylate AT airiyaningak methyl9ar10s11r13as13bs9oxo6799a1011hexahydro5h13bh1113aepoxypyrrolo213414diazepino21aisoindole10carboxylate AT nikitinaeugeniyav methyl9ar10s11r13as13bs9oxo6799a1011hexahydro5h13bh1113aepoxypyrrolo213414diazepino21aisoindole10carboxylate AT sorokinaelenaa methyl9ar10s11r13as13bs9oxo6799a1011hexahydro5h13bh1113aepoxypyrrolo213414diazepino21aisoindole10carboxylate AT khrustalevvictorn methyl9ar10s11r13as13bs9oxo6799a1011hexahydro5h13bh1113aepoxypyrrolo213414diazepino21aisoindole10carboxylate |