1678-14-4

Usage

Classification

Pyranone derivative

Structure

Contains a pyran ring and a ketone group

Uses

Commonly used in organic synthesis and pharmaceutical research

Targeted properties

Potential anti-inflammatory and antioxidant properties

Importance

Valuable building block for the development of new drugs and materials

Upstream product

• 1469-93-8 1,5-bis(4-methoxyphenyl)-1,3,5-pentanetrione 
• 768-60-5 4-methoxyphenylacetylen 
• 13422-77-0 3-(4-methoxy-phenyl)-3-oxo-propionic acid 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 
• 34793-63-0 1,5-bis(4-methoxyphenyl)penta-1,4-diyn-3-one 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 55991-65-6 [1-(4-methoxyphenyl)vinyloxy]trimethylsilane 
• 55991-69-0 5-(4-methoxyphenyl)-2,3-dihydro-2,3-furandione 
• 58168-97-1 1,2,4,5-tetrabromo-1,5-bis-(4-methoxy-phenyl)-pentan-3-one 

Downstream Products

• 101894-16-0 2,6-bis-(4-methoxy-phenyl)-pyran-4-thione 
• 102022-70-8 2,6-bis-(4-methoxy-phenyl)-pyran-4-one oxime 
• 100-09-4 4-methoxybenzoic acid 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Relevant academic research and scientific papers

Regiodivergent Hydration-Cyclization of Diynones under Gold Catalysis

Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration-oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology in the total synthesis of polyporapyranone B was demonstrated.

Synthesis of γ-pyrones via decarboxylative condensation of β-ketoacids

Abstract: This manuscript describes the convergent synthesis of aryl- and alkyl-disubstituted γ-pyrones from β-ketoacids. The reaction proceeds in the presence of trifluoromethanesulfonic anhydride via an unprecedented decarboxylative auto-condensation of the starting material. Herein, the scope and limitations of this transformation are reported. Graphical abstract: [Figure not available: see fulltext.]

Atom-economic synthesis of 4-pyrones from diynones and water

Transition-metal-free synthesis of 4-pyrones via TfOH-promoted nucleophilic addition/cyclization of diynones and water has been developed. This transformation is simple, atom economical and environmentally benign, providing rapid and efficient access to s

New strong base synthesis of symmetrical 1,5-diaryl-1,3,5-pentanetriones from acetone and benzoate esters

Lithium hexamethyldisilazide (LiHMDS) was used to condense substituted benzoate esters with acetone to afford symmetrical 1,5-diaryl-1,3,5- pentanetriones that were isolated, characterized (including a representative X-ray crystallographic analysis), and

Thermal addition reaction of aroylketene with 1-aryl-1- trimethylsilyloxyethylenes: Aromatic substituent effects of aroylketene and aryltrimethylsilyloxyethylene on their reactivity

The thermal addition reaction of various aroylketenes (C) generated by the thermolysis of 5-aryldioxofurans (A) to 1-aryl-1-trimethylsilyloxyethylenes gave 1,5-diarylpentane-1,3,5-triones (D) and 2,6-diaryl-4H-pyran-4-ones (E). The introduction of electron withdrawing substituents in the aroylketene and of electron donating substituents facilitated the addition reaction. The observed substituent effects and the reaction mechanism are interpreted in terms of molecular orbital analyses.