34253-29-7Relevant academic research and scientific papers
A combined experimental and theoretical study of the supramolecular self-assembly of the natural benzopyran 2,2-dimethyl-3-hydroxy-6-acetyl-chromane and its isomeric benzofuran 10,11-dihydro-10-hydroxytremetone
Gil, Diego M.,Lizarraga,Echeverría,Piro,Catalán,Ben Altabef
, p. 164 - 178 (2017/06/09)
Epoxidation of 4HMBA, the main metabolite of the medicinal plant Sencecionutans, produces an unstable epoxide eventually giving rise to a mixture of four derivatives, three of them previously reported as natural products. The epoxide product easily undergoes an intra-molecular attack of the phenolic hydroxyl against the epoxide group carbons to produce either a benzofuran or a chromane derivative. When dissolved in methanol-water mixture at room temperature the epoxide is completely solvolyzed to give the corresponding diol (hydrolysis) or vicinal hydroxyl-methoxy (methanolysis) derivative. All the compounds involved in the above reactions were characterized by IR, Raman, H NMR and UV–vis spectroscopies, and by mass spectrometry. Density functional theory (DFT) computations were used to optimize the structure conformations. The optimized structures were further subjected to a Natural Bond Orbital (NBO) and electrostatic potentials analysis. The crystal structures of the title compounds (for short, 3 and 4 respectively) were determined by X-ray diffraction methods. Compound 3 crystallizes in the triclinic P-1 space group with a = 6.4289 (6) ?, b = 8.7120 (6) ?, c = 10.952 (1) ?, α = 92.280 (7)°, β = 95.738 (7)°, γ = 103.973 (7)°, and Z = 2 molecules per unit cell and 4 in the monoclinic P21/c space group with a = 11.2891 (6) ?, b = 9.1902 (4) ?, c = 12.4272 (7) ?. Β = 113.689 (7)°, and Z = 4. In 3 neighboring molecules are linked to each other by OH?O (keto) bonds giving rise to a polymeric structure. In 4 the OH group is a bifurcate H-bond donor. It forms a weak intra-molecular OH?O (furan) bond and also a much stronger inter-molecular O[sbnd]H?O (keto) bond giving rise to a zig-zag polymeric structure. A detailed analysis of the solid state molecular interactions of compounds 3 and 4 has been performed using Hirshfeld surface analysis and their associated 2D fingerprint plots.
Synthesis of Naturally Occurring p-Hydroxyacetophenone Derivatives, III
Bohlmann, Ferdinand,Stoehr, Frank-Michael
, p. 185 - 191 (2007/10/02)
Starting with different p-hydroxyacetophenone dervatives ten naturally occurring compounds have been synthesized.The synthesis of the vinyl chromene 18 gave unexpected difficulties as the dehydration of the corresponding alcohol was not successful.However
