55919-72-7

Usage

Chemical class

Ketones

Derivatives

5-acetyl-2,3-dimethoxy-phenyl and 4,5-dimethoxy-phenyl

Structure

Contains a ketone group attached to a phenyl ring

Usage

Often used in organic synthesis and pharmaceutical research

Intermediate

Valuable intermediate for the production of various other organic compounds

Potential applications

Development of new drugs or pharmaceutical compounds due to its interesting chemical structure

Upstream product

• 29799-22-2 1,1'-(6,6'-dihydroxy-5,5'-dimethoxy-(1,1'-biphenyl)-3,3'-diyl)-bis-(ethan-1-one) 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Lignin model compounds: 4,4′-O-dimethyldehydrodiacetovanillone and 4,4′-O-diethyldehydrodiacetovanillone

The title compounds, 5,5′-diacetyl-2,2′,3,3′-tetramethoxy-1,1′-biphenyl, C20H22O6, and 5,5′-diacetyl-2,2′-diethoxy-3,3′-dimethoxy-1,1′-biphenyl (IUPAC nomenclature), C22H26O6, correspond to the 5,5′-biphenyl-type lignin model compound. They were synthesized from dehydrodiacetovanillone by alkylation with CH3I and C2H5I. In the former compound, all non-H atoms in the asymmetric unit are planar except for one C atom. In the latter compound, there are two molecules of different conformations, one of which is affected by disorder.

Stereoselective oxazaborolidine-borane reduction of biphenyl alkyl diketones-lignin models: Enantiopure dehydrodiapocynol derivatives

Asymmetric reduction of two conformationally flexible biphenyl alkyl diketones 9 and 10 with (R)-oxazaborolidine 3-borane system was successfully carried out and the corresponding biphenyl alcohols 11 and 12 were obtained in high yield and e.e. with predominance of the homochiral (S,S) dicarbinols. The absolute configuration of diastereopure dehydrodiapocynol derivative (S,S)-14 was assigned by crystallographic analysis which confirms the known stereochemical course of CBS-catalysed reduction of ketones and gives useful information on spatial arrangement.