| Chalcone epoxide intermediates in the syntheses of lignin-related phenylcoumarans. | |
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MedLine Citation:
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PMID: 17008753 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Compounds (2R*,3S*)-1-(3,4-dimethoxyphenyl)-3-{3-methoxy-2-[(2R*)-tetrahydropyran-2-yloxy]phenyl}-2,3-epoxy-1-propanone, C23H26O7, (I), and trans-1-(3,4-dimethoxyphenyl)-3-[3-methoxy-2-(methoxymethoxy)phenyl]-2,3-epoxy-1-propanone, C20H22O7, (II), were obtained on epoxidation of chalcones. The stereochemistries of (I) and (II) were elucidated. In both compounds, the substituents on the oxirane ring are trans-oriented. Compound (I) was obtained together with a diastereometric form that differs from (I) with respect to the configuration of the asymmetric C atom in the tetrahydropyran group. The geometries of the substituted oxirane rings of (I) and (II) are very similar. The hydrogen-bonding patterns, mediated via weak C-H...O interactions, differ considerably. The crystal structures of (I) and (II) are compared with those of related chalcone epoxides. The conversion of (I) and (II) into lignin-related phenylcoumarans is discussed. |
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Authors:
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Vratislav Langer; Shiming Li; Knut Lundquist |
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Publication Detail:
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Type: Journal Article Date: 2006-09-21 |
Journal Detail:
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Title: Acta crystallographica. Section C, Crystal structure communications Volume: 62 ISSN: 0108-2701 ISO Abbreviation: Acta Crystallogr C Publication Date: 2006 Oct |
Date Detail:
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Created Date: 2006-09-29 Completed Date: 2007-06-04 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 8305826 Medline TA: Acta Crystallogr C Country: Denmark |
Other Details:
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Languages: eng Pagination: o625-7 Citation Subset: IM |
Affiliation:
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Environmental Inorganic Chemistry, Department of Chemical and Biological Engineering, Chalmers University of Technology, SE-41296 Göteborg, Sweden. langer@chalmers.se |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Benzofurans
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chemical synthesis*,
chemistry* Chalcones / chemistry* Crystallography, X-Ray Hydrogen Bonding Lignin / chemistry* Models, Molecular Molecular Structure |
| Chemical | |
Reg. No./Substance:
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0/Benzofurans; 0/Chalcones; 496-16-2/coumaran; 5411-12-1/chalcone epoxide; 9005-53-2/Lignin |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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