(6bS*,14R*,14aR*)-Methyl 14-(4-methylphenyl)-7-oxo-6b,6c,7,12b,14,14a-hexahydro-1H-pyrano[3,2-c:5,4-c′]dichromene-14a-carboxylate

Abstract

Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.003 Å; R factor = 0.045; wR factor = 0.133; data-to-parameter ratio = 14.6.In the title compound, C 28 H 22 O 6 , the chromeno ring system is almost planar, with a dihedral angle between the mean planes of the pyran and benzene rings of 1.87 (8) . The pyran ring bearing the methylphenyl substituent has a half-chair conformation while the other pyran ring has an envelope conformation with the tetrasubstituted C atom as the flap. The benzene ring of the chromeno ring system is inclined to the benzene ring fused to the latter pyran ring by 74.66 (9) . These aromatic rings are inclined to the 4-methylphenyl ring by 52.67 (9) and 66.63 (10) , respectively. In the crystal, molecules are linked via C-HÁ Á ÁO hydrogen bonds, forming a two-dimensional network parallel to the bc plane. Related literature

Methyl (6R*,6aR*,12bR*)-2,4-dimethyl-6-(2-methylphenyl)-1,3-dioxo-2,3,4,6a,7,12b-hexahydro-1H,6H-chromeno[4′,3′:4,5]pyrano[2,3-d]pyrimidine-6a-carboxylate

“…data reports C12(position 6a) and C6(position 12b), respectively (see Scheme). The bond distances and bond angles are in good agreement with the values reported for similar structures (Swaminathan et al, 2015;Ponnusamy et al, 2013). The sp 2 hybridization of atoms N1 and N2 are indicated by the sum of the bond angles of 359.8 and 360.0 , respectively.…”

“…The title compound was synthesized following a published procedure (Ponnusamy et al, 2013;Swaminathan et al, 2015). A mixture of (E)-methyl 2-((2-formylphenoxy)methyl)-3-(2methylphenyl) acrylate (0.448 g, 1 mmol) and N,N-dimethylbarbutric acid (0.156 g, 1 mmol) was placed in a round-bottom flask and melted at 453 K for 1 h. After completion of the reaction, as indicated by TLC, the crude product was washed with 5 ml of an ethylacetate and hexane mixture (1:49) which successfully provided the pure title compound as a colourless solid in 97% yield.…”

Crystal structures and conformational analyses of three pyranochromene derivatives

“…The bond distances and bond angles in compounds (I)-(III) are in agreement with those in the reported structures. For example: compounds (I) and (II) exhibits structural similarities with entries LESWIR (Ponnusamy et al, 2013) which has a toluene rather than a phenyl substituent on ring (B), OLEZIP (Kathiravan & Raghunathan, 2010) which has a 4-methoxyphenyl substituent, and AZUKIQ (Swaminathan et al, 2011) which has a 2-chlorophenyl substituent. Compound (III) is similar to entries WUNNAV (Bakthadoss et al, 2009), AXACAE (Kanchanadevi et al, 2011) and WUNNEZ (Bakthadoss et al, 2009), but only the last compound also has a cabonitrile side chain.…”

Methyl 11,14,16-triphenyl-8,12-dioxa-14,15-diazatetracyclo[8.7.0.02,7.013,17]heptadeca-2(7),3,5,13(17),15-pentaene-10-carboxylate

“…For the biological activity of 4H-chromenes, see: Cai et al (2006); Gabor (1988); Brooks (1998); Valenti et al (1993); Tang et al (2007). For a related structure, see: Ponnusamy et al (2013).…”