Document Detail

Chalcone epoxide intermediates in the syntheses of lignin-related phenylcoumarans.
MedLine Citation:
PMID:  17008753     Owner:  NLM     Status:  MEDLINE    
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.
Vratislav Langer; Shiming Li; Knut Lundquist
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Publication Detail:
Type:  Journal Article     Date:  2006-09-21
Journal Detail:
Title:  Acta crystallographica. Section C, Crystal structure communications     Volume:  62     ISSN:  0108-2701     ISO Abbreviation:  Acta Crystallogr C     Publication Date:  2006 Oct 
Date Detail:
Created Date:  2006-09-29     Completed Date:  2007-06-04     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8305826     Medline TA:  Acta Crystallogr C     Country:  Denmark    
Other Details:
Languages:  eng     Pagination:  o625-7     Citation Subset:  IM    
Environmental Inorganic Chemistry, Department of Chemical and Biological Engineering, Chalmers University of Technology, SE-41296 Göteborg, Sweden.
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MeSH Terms
Benzofurans / chemical synthesis*,  chemistry*
Chalcones / chemistry*
Crystallography, X-Ray
Hydrogen Bonding
Lignin / chemistry*
Models, Molecular
Molecular Structure
Reg. No./Substance:
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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