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Chalcone epoxide intermediates in the syntheses of lignin-related phenylcoumarans

Vratislav Langer (Institutionen för kemi- och bioteknik, Oorganisk miljökemi) ; Shiming Li (Institutionen för kemi- och bioteknik, Skogsindustriell kemiteknik) ; Knut Lundquist (Institutionen för kemi- och bioteknik, Skogsindustriell kemiteknik)
Acta Crystallographica, Section C: Crystal Structure Communications (0108-2701). Vol. C62 (2006), 10, p. o625-o627.
[Artikel, refereegranskad vetenskaplig]

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.

Nyckelord: X-ray strucrure determination, conformation, stereochemistry, hydrogen bonds



Denna post skapades 2007-03-12.
CPL Pubid: 22777

 

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Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Oorganisk miljökemi (2005-2014)
Institutionen för kemi- och bioteknik, Skogsindustriell kemiteknik (2005-2014)

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