57403-53-9

Basic information

• Product Name: 1,3-Dioxane-4,6-dione, 2,2-dimethyl-5-(1-phenylethylidene)-
• CAS NO: 57403-53-9
• Molecular Formula: C14H14O4
• Molecular Weight: 246.263
• Mol File: 57403-53-9.mol

Chemical Properties

• CAS DataBase Reference: 1,3-Dioxane-4,6-dione, 2,2-dimethyl-5-(1-phenylethylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxane-4,6-dione, 2,2-dimethyl-5-(1-phenylethylidene)-(57403-53-9)
• EPA Substance Registry System: 1,3-Dioxane-4,6-dione, 2,2-dimethyl-5-(1-phenylethylidene)-(57403-53-9)

Safety Data

• Hazardous Substances Data: 57403-53-9(Hazardous Substances Data)

Upstream product

• 2033-24-1 cycl-isopropylidene malonate 
• 98-86-2 acetophenone 

Relevant articles and documents

Asymmetric synthesis of all-carbon benzylic quaternary stereocenters via Cu-catalyzed conjugate addition of dialkylzinc reagents to 5-(1-arylalkylidene) Meldrum's acids

The asymmetric synthesis of all-carbon benzylic quaternary stereocenters has been successfully achieved through copper-catalyzed addition of dialkylzinc reagents to 5-(1-arylalkylidene) and 5-(dihydroindenylidene) Meldrum's acids in the presence of phosph

Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones

Upon Br?nsted base organocatalysis, ketone-derived alkylidene Meldrum's acids proved to be competent vinylogous platforms able to undergo a formal (4+2) cycloaddition reaction with dihydro-2,3-furandione, providing an unprecedented route to 3,6-dihydropyran-2-ones as spiro[4.5]decane derivatives with up to 98 % ee thanks to the commercially available Takemoto catalyst. Preliminary investigation showed that this reaction could be extended to other activated ketones, establishing these alkylidene Meldrum's acids as a novel C4-synthon in the vinylogous series.

Synthesis of Cyclopentadienes for Cyclopentadienyl Ligands via Cp*RhIII-Catalyzed Formal sp3C-H Activation/Spiroannulations

An efficient Cp*RhIII-catalyzed formal C(sp3)-H activation/spiroannulation of alkylidene Meldrum's acids with alkynes has been developed using catalytical Cu(OAc)2 and air as the oxidant. This reaction demonstrates a new and straightforward approach to spirocyclopentadienes with Meldrum's acid moieties in good to excellent yields under mild reaction conditions with a broad substrate scope. Notably, this protocol provides a novel and straightforward approach to cyclopentadienes with various substitution patterns and the corresponding cyclopentadienyl-type ligands from simple substrates.

Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide

The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.

Auto Tandem Catalysis: Asymmetric Vinylogous Cycloaddition/Kinetic Resolution Sequence for the Enantioselective Synthesis of Spiro-Dihydropyranone from Benzylidene Meldrum's Acid

A catalytic enantioselective vinylogous domino reaction has been achieved from ketone-derived benzylidene Meldrum's acid and α-ketolactones to provide spirolactone dihydropyranones with more than 99% ee. An Auto Tandem Catalysis (ATC) process resulting fr

Rapid Access to Thiolactone Derivatives through Radical-Mediated Acyl Thiol-Ene and Acyl Thiol-Yne Cyclization

A new synthetic approach to thiolactones that employs an efficient acyl thiol-ene (ATE) or acyl thiol-yne (ATY) cyclization to convert unsaturated thiocarboxylic acid derivatives into thiolactones under very mild conditions is described. The high overall yields, fast kinetics, high diastereoselectivity, excellent regiocontrol, and broad substrate scope of these reaction processes render this a very useful approach for diversity-oriented synthesis and drug discovery efforts. A detailed computational rationale is provided for the observed regiocontrol.

Expedient synthesis of complex γ-butyrolactones from 5-(1-arylalkylidene) meldrums acids via sequential conjugate alkynylation/Ag(I)-catalyzed lactonization

The conjugate alkynylation of alkylidene Meldrums acids with alkynylalanes and alkynyl Grignards allows for the formation of propargylic all-carbon quaternary stereocenters in high yields. Ag2CO3-catalyzed intramolecular cyclization

A practical and convenient protocol for the synthesis of (E)-α,β-unsaturated acids

α,β-Unsaturated acids are very useful and versatile reagents in organic synthesis. A novel, practical, and convenient catalytic protocol comprising FeCl3·6H2O (0.5 mol %) and H 2O (1 equiv) in CH3NO2 is described for the rapid synthesis of α,β-unsaturated acids with high E-stereoselectivity under both microwave and conventional heating conditions with high TON and TOF values. This powerful approach efficiently demonstrated the utility of biomass derived aldehydes to build chemical agents used as fuel additives. The method proved to be scalable to gram scale synthesis.

Asymmetric synthesis of all-carbon benzylic quaternary stereocenters via conjugate addition to alkylidene and indenylidene Meldrum's acids

(Chemical Equation Presented) A systematic study outlining the enantioselective 1,4-addition of dialkylzinc reagents to 5-(1-arylalkylidene) and indenylidene Meldrum's acids is presented. Variation of the aryl and alkyl groups present on the alkylidene wa