31380-12-8

Upstream product

• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 139140-13-9 1-{4-[(tert-butyldimethylsilyl)oxy]-2,6-dihydroxyphenyl}ethan-1-one 

Downstream Products

• 1669423-79-3 3-(4-fluorophenyl)-1-(5-hydroxy-2,2,8,8-tetramethyl-2H,8H-pyrano[2,3-f]chromen-6-yl)-propenone 
• 1613023-64-5 3-(2-fluorophenyl)-1-(5-hydroxy-2,2,8,8-tetramethyl-2H,8H-pyrano[2,3-f]chromen-6-yl)-propenone 
• 910621-15-7 1-(5-hydroxy-2,2,8,8-tetramethyl-2H,8H-pyrano[2,3-f]chromen-6-yl)-3-phenylpropenone 
• 1613023-76-9 2-(4-methoxyphenyl)-6,6,10,10-tetramethyl-2,3-dihydro-6H,10H-dipyrano[2,3-f;2′,3′-h]chromen-4-one 
• 1613023-75-8 2-(3-methoxyphenyl)-6,6,10,10-tetramethyl-2,3-dihydro-6H,10H-dipyrano[2,3-f;2′,3′-h]chromen-4-one 
• 1613023-74-7 2-(2,4-difluorophenyl)-6,6,10,10-tetramethyl-2,3-dihydro-6H,10H-dipyrano[2,3-f;2′,3′-h]chromen-4-one 
• 1613023-73-6 2-(4-fluorophenyl)-6,6,10,10-tetramethyl-2,3-dihydro-6H,10H-dipyrano[2,3-f;2′,3′-h]chromen-4-one 
• 1613023-72-5 2-(3-fluorophenyl)-6,6,10,10-tetramethyl-2,3-dihydro-6H,10H-dipyrano[2,3-f;2′,3′-h]chromen-4-one 
• 1613023-71-4 2-(2-fluorophenyl)-6,6,10,10-tetramethyl-2,3-dihydro-6H,10H-dipyrano[2,3-f;2′,3′-h]chromen-4-one 
• 1613023-70-3 6,6,10,10-tetramethyl-2-phenyl-2,3-dihydro-6H,10H-dipyrano[2,3-f;2′,3′-h]chromen-4-one 
• 89354-00-7 (E)-1-(5-hydroxy-2,2,8,8-tetramethyl-2H,8H-pyrano [2,3-f]chromen-6-yl)-3-phenylprop-2-en-1-one 

Relevant academic research and scientific papers

Natural product rottlerin derivatives targeting quorum sensing

Rottlerin is a natural product consisting of chalcone and flavonoid scaffolds, both of which have previously shown quorum sensing (QS) inhibition in various bacteria. Therefore, the unique rottlerin scaffold highlights great potential in inhibiting the QS

Synthesis, structural elucidation, intramolecular hydrogen bonding and DFT studies of quinoline-chalcone-chromene hybrids

Eight hydroxyquinoline-chromene chalcones, of which six were new, were synthesized using the Vilsmeier-Haack reaction and Claisen-Schmidt condensation. These contain either mono or dichromene functionality. The hydroxyl proton chemical shift of both types of compounds at varying temperature indicated weakened hydrogen bonds with an increase in temperature, however there was no significant difference to the slopes of the OH chemical shift curves (3.4 x10-3 for the 2-methoxychromene derivative and 3.1 x10-3 for the 6-methoxydichromene derivative. Potential energy scans of these two compounds were obtained using B3LYP/6-311 G level theory in the gas phase, and showed the enol form to be most stable for both molecules and that the energy barrier to make proton transfer possible is 5.076 and 3.989 Kcal mol-1 for the 2-methoxychromene and 6-methoxydichromene derivatives respectively.

Synthesis and structure elucidation of a series of pyranochromene chalcones and flavanones using 1D and 2D NMR spectroscopy and X-ray crystallography

A series of novel pyranochromene chalcones and corresponding flavanones were synthesized. This is the first report on the confirmation of the absolute configuration of chromene-based flavanones using X-ray crystallography. These compounds were characterized by 2D NMR spectroscopy, and their assignments are reported herein. The 3D structure of the chalcone 3b and flavanone 4g was determined by X-ray crystallography, and the structure of the flavanone was confirmed to be in the S configuration at C-2. Copyright

Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II

Herein is reported an efficient method for the synthesis of 2,2-dimethyl-2H-chromenes in a single step from the corresponding phenol and 3-methyl-2-butenal via microwave irradiation in CDCl3. This protocol features a mild reaction environment (neutral, no added catalyst) which yields regioselective formation of the chromene and displays tolerance toward acid- and base-sensitive protecting groups.

Efficient one-pot trans-dihydroxylation of 2H-pyrans using dimethyldioxirane (DMD): synthesis of trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin natural products

An efficient one-pot formation of trans-diols on 2H-pyranyl rings was achieved by dimethyldioxirane in wet acetone. This new methodology was applied to the synthesis of natural products containing trans-diol on the pyranyl rings such as trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin.

Efficient synthesis of octandrenolone and related dipyranoacetophenones

Octandrenolone (1) was prepared in high yield by condensation of 2',4',6'-trihydroxyacetophenone with 3-chloro-3-methylbut-1-yne in the presence of a catalytic amount of copper(I) iodide. Methylation of 1 afforded O-methyloctandrenolone (2). Oxidation of 2 with m-chloroperoxybenzoic acid followed by hydrolysis gave the racemic trans-(+)-1-(9,10-dihydro-9,10- dihydroxy-5-methoxy-2,2,8,8-tetramethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-6- yl)ethanone (3), which confirmed the structure of the natural product previously isolated from Melicope erromangensis.