Novel diastereoisomers of C21H20O3 obtained from the cathodic reduction of methyl (2E)-3-[2-(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate
The diastereoisomeric title compounds, 5 and 6, were obtained as a result of intramolecular electrohydrocyclisation of methyl (2E)-3-[2- (2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate. The common feature of the molecular structures is the presence of a central, eight-me...
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| Language: | English |
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De Gruyter for Oldenbourgh Verlag
2017
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| Online Access: | http://eprints.sunway.edu.my/711/ http://eprints.sunway.edu.my/711/1/Tienink%20Novel%20diastereoisomers%20Z.%20Kristallogr.%202017%20232%20781.pdf |
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| author | Curilazo, Ricardo Pardine, Vera L Viertler, Hans Zukerman-Schpector, Julio Tiekink, Edward R. T. * |
| author_facet | Curilazo, Ricardo Pardine, Vera L Viertler, Hans Zukerman-Schpector, Julio Tiekink, Edward R. T. * |
| author_sort | Curilazo, Ricardo |
| building | SU Institutional Repository |
| collection | Online Access |
| description | The diastereoisomeric title compounds, 5 and 6, were obtained as a result of intramolecular electrohydrocyclisation of methyl (2E)-3-[2-
(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate. The common feature of the molecular structures is the presence of a central, eight-membered, –C(H)–C(H)–C C–(CH2)2–C C, ring appended to a cyclopentenyl and two phenyl rings. This study represents an
unprecedented structural characterisation of such an atomic/bonding arrangement. The distinctive feature of the structures relates to the conformation of the central rings, i.e. approximating a boat in 5 and a chair in 6.
This difference in molecular conformations arises from the different configurations at the methine-C atoms of the cyclopentenyl ring, i.e. R- and S-(or S- and R-) in 5 as opposed to R- and R- (or S- and S-) in 6. In each case,
the hydroxyl-OH forms an intramolecular hydrogen-bond to the adjacent carbonyl-O atom so the molecular packing in each of 5 and 6 is sustained by non-conventional interactions. A three-dimensional architecture in 5
arises from a combination of phenyl-C–H…O(carbonyl) and methyl- and methylene-C–H…p contacts. In the crystal of 6, supramolecular chains with a zig-zag topology along the c-axis are formed via methyl-C–H…O(hydroxyl); the chains pack with no directional interactions between them. |
| first_indexed | 2025-11-14T21:14:32Z |
| format | Article |
| id | sunway-711 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:14:32Z |
| publishDate | 2017 |
| publisher | De Gruyter for Oldenbourgh Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-7112020-10-07T09:40:21Z http://eprints.sunway.edu.my/711/ Novel diastereoisomers of C21H20O3 obtained from the cathodic reduction of methyl (2E)-3-[2-(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate Curilazo, Ricardo Pardine, Vera L Viertler, Hans Zukerman-Schpector, Julio Tiekink, Edward R. T. * QD Chemistry The diastereoisomeric title compounds, 5 and 6, were obtained as a result of intramolecular electrohydrocyclisation of methyl (2E)-3-[2- (2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate. The common feature of the molecular structures is the presence of a central, eight-membered, –C(H)–C(H)–C C–(CH2)2–C C, ring appended to a cyclopentenyl and two phenyl rings. This study represents an unprecedented structural characterisation of such an atomic/bonding arrangement. The distinctive feature of the structures relates to the conformation of the central rings, i.e. approximating a boat in 5 and a chair in 6. This difference in molecular conformations arises from the different configurations at the methine-C atoms of the cyclopentenyl ring, i.e. R- and S-(or S- and R-) in 5 as opposed to R- and R- (or S- and S-) in 6. In each case, the hydroxyl-OH forms an intramolecular hydrogen-bond to the adjacent carbonyl-O atom so the molecular packing in each of 5 and 6 is sustained by non-conventional interactions. A three-dimensional architecture in 5 arises from a combination of phenyl-C–H…O(carbonyl) and methyl- and methylene-C–H…p contacts. In the crystal of 6, supramolecular chains with a zig-zag topology along the c-axis are formed via methyl-C–H…O(hydroxyl); the chains pack with no directional interactions between them. De Gruyter for Oldenbourgh Verlag 2017 Article PeerReviewed text en http://eprints.sunway.edu.my/711/1/Tienink%20Novel%20diastereoisomers%20Z.%20Kristallogr.%202017%20232%20781.pdf Curilazo, Ricardo and Pardine, Vera L and Viertler, Hans and Zukerman-Schpector, Julio and Tiekink, Edward R. T. * (2017) Novel diastereoisomers of C21H20O3 obtained from the cathodic reduction of methyl (2E)-3-[2-(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate. Zeitschrift fur Kristallographie, 232 (11). pp. 781-788. ISSN 0044-2968 |
| spellingShingle | QD Chemistry Curilazo, Ricardo Pardine, Vera L Viertler, Hans Zukerman-Schpector, Julio Tiekink, Edward R. T. * Novel diastereoisomers of C21H20O3 obtained from the cathodic reduction of methyl (2E)-3-[2-(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate |
| title | Novel diastereoisomers of C21H20O3 obtained from the cathodic reduction of methyl (2E)-3-[2-(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate |
| title_full | Novel diastereoisomers of C21H20O3 obtained from the cathodic reduction of methyl (2E)-3-[2-(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate |
| title_fullStr | Novel diastereoisomers of C21H20O3 obtained from the cathodic reduction of methyl (2E)-3-[2-(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate |
| title_full_unstemmed | Novel diastereoisomers of C21H20O3 obtained from the cathodic reduction of methyl (2E)-3-[2-(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate |
| title_short | Novel diastereoisomers of C21H20O3 obtained from the cathodic reduction of methyl (2E)-3-[2-(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate |
| title_sort | novel diastereoisomers of c21h20o3 obtained from the cathodic reduction of methyl (2e)-3-[2-(2-{2-[(1e)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/711/ http://eprints.sunway.edu.my/711/1/Tienink%20Novel%20diastereoisomers%20Z.%20Kristallogr.%202017%20232%20781.pdf |