85920-63-4

Usage

Uses

Used in Pharmaceutical Industry:
5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione is used as a key intermediate in the synthesis of Bicyclic β-Lactams and Oxazinones. These compounds are of significant interest in the pharmaceutical industry due to their potential as novel antibiotics and other therapeutic agents. The synthesis of these bicyclic compounds is achieved through cycloaddition and metathesis reactions starting from Acyl/Carbamoyl-dimethyl-dioxa-diones.

Upstream product

• 2033-24-1 cycl-isopropylidene malonate 
• 75-36-5 acetyl chloride 
• 78-39-7 Triethyl orthoacetate 
• 112182-59-9 2,2-dimethyl-5-[1-(methylthio)ethylidene]-1,3-dioxane-4,6-dione 
• 64-19-7 acetic acid 

Downstream Products

• 85920-68-9 (9'-Bromo-1'-nonyl)-3-oxobutanoate 
• 77060-85-6 trans-α-phenylcinnamyl acetoacetate 
• 77060-84-5 cis-α-phenylcinnamyl acetoacetate 
• 118798-09-7 3-Oxo-butyric acid 3-formyl-2,4,4-trimethyl-cyclohex-2-enyl ester 
• 118798-08-6 2,6,6-Trimethyl-3-(3-oxo-butyryloxy)-cyclohex-1-enecarboxylic acid methyl ester 
• 118798-07-5 3-Oxo-butyric acid 3-acetyl-2,4,4-trimethyl-cyclohex-2-enyl ester 
• 27991-08-8 N-acetoacetylphenylhydroxyloamine 
• 1118-84-9 allyl acetoacetate 
• 93598-46-0 5-acetyl-3-cyclohexyl-2-cyclohexylimino-3,4,5,6-tetrahydro-1,3-oxazine-4,6-dione 
• 5848-33-9 2-methyl-4H-pyran-4-one 
• 22717-41-5 4-ethyl-3-methyl-1-phenylpyrazol-5-one 
• 192209-26-0 4-n-hexyl-3-methyl-1-phenylpyrazol-5-one 
• 24246-11-5 ethyl-2-(4,5-dihydro-3-methyl-5-oxo-1-phenyl-1H-pyrazol-4-yl)acetate 
• 17900-68-4 3,4-dimethyl-1-phenyl-pyrazolin-5-one 

Relevant academic research and scientific papers

Acylation studies with Meldrum's acid

Meldrum's acid (1) on bisacylation with succinyl chloride afforded a neutral diketo product (2); however, the dimer enolic products (3) with acidic nature resulted in glutaryl and adipyl dichlorides. Monoacylation of (1) with acetyl chloride gave acidic 5-acetyl Meldrum's acid (4) in enol form. Copyright Taylor & Francis, Inc.

A synthetic approach to 5/5/6-polycyclic tetramate macrolactams of the discodermide type

A flexible synthetic route to the 16-membered tetramate-embedding macrocyclic scaffold present in various polycyclic tetramate macrolactams (PTMs) was developed which differs from the seminal synthesis of ikarugamycin by Boeckman Jr. in protecting groups and the order of connections. We also devised a short approach to various stereoisomers of the 5/5/6-tricarbocyclic motif found in discodermide and other PTMs, starting from the Weiss’ diketone.

Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions

An electrochemical oxidative cross-coupling reaction between 2.5-substituted-pyrazolin-5-ones and ammonium thiocyanate has been developed, which resulted in a series of unprecedented cross-coupling products under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions. It is worth noting that since the resulting cross-coupling products are nearly insoluble in MeCN, the pure product could be afforded without silica gel column purification. In addition, the prepared ammonium oxides are versatile building blocks for synthesizing functionalized pyrazole derivatives.

AN IMPROVED PROCESS FOR THE PREPARATION OF 4-({(1 R)-2-[5-(2-FLUORO-3METHOXYPHENYL)-3-{[2-FLUORO-6-(TRIFLUORO METHYL) PHENYL]METHYL}-4-METHYL-2,6-DIOXO-3,6DIHYDROPYRIMIDIN-1(2 H)-YL]-1-PHENYLETHYL}AMINO)BUTANOIC ACID OR ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to an improved process for the preparation of 4- ({(1R) -2- [5- (2-fluoro- 3- methoxy phenyl) – 3 - {[ 2-fluoro- 6-(trifluoro methyl) phenyl] methyl} -4-methyl- 2,6-dioxo- 3,6-dihydropyrimidin-1(2H)-yl]-1-phenylethyl}amino) butanoic acid of formula (I) or its pharmaceutically acceptable salts. The compound of formula (I) is represented by the following structural formula.

5-Carbonyl-1,3-oxazine-2,4-diones from N-Cyanosulfoximines and Meldrum's Acid Derivatives

At elevated temperatures, N-cyanosulfoximines react with Meldrum's acid derivatives to give sulfoximines with N-bound 5-carbonyl-1,3-oxazine-2,4-dione groups. A representative product was characterized by single-crystal X-ray structure analysis. The product formation involves an unexpected molecular reorientation requiring several sequential bond-forming and-cleaving processes.

Control of β-Branching in Kalimantacin Biosynthesis: Application of 13C NMR to Polyketide Programming

The presence of β-branches in the structure of polyketides that possess potent biological activity underpins the widespread importance of this structural feature. Kalimantacin is a polyketide antibiotic with selective activity against staphylococci, and its biosynthesis involves the unprecedented incorporation of three different and sequential β-branching modifications. We use purified single and multi-domain enzyme components of the kalimantacin biosynthetic machinery to address in vitro how the pattern of β-branching in kalimantacin is controlled. Robust discrimination of enzyme products required the development of a generalisable assay that takes advantage of 13C NMR of a single 13C label incorporated into key biosynthetic mimics combined with favourable dynamic properties of an acyl carrier protein. We report a previously unassigned modular enoyl-CoA hydratase (mECH) domain and the assembly of enzyme constructs and cascades that are able to generate each specific β-branch.

Acyl/aroyl Meldrum's acid as an enol surrogate for the direct organocatalytic synthesis of α,β-unsaturated ketones

The operationally simple, robust and straightforward organocatalytic protocol is developed for the synthesis of E-selective α,β-unsaturated ketones. The method utilizes simple and easily accessible starting materials such as Meldrum's acid, carboxylic acid, aldehyde and simple bifunctional amine catalyst. The tandem organocatalytic process utilizes acyl/aroyl Meldrum's acid as an enol surrogate for the effective Doebner-Knoevenagel type condensation reactions. A wide variety of aldehydes, carboxylic acids and base sensitive functional groups are well tolerated under the mild reaction conditions.

3-Oxoisoxazole-2(3H)-carboxamides and isoxazol-3-yl carbamates: Resistance-breaking acetylcholinesterase inhibitors targeting the malaria mosquito, Anopheles gambiae

To identify potential selective and resistance-breaking mosquitocides against the African malaria vector Anopheles gambiae, we investigated the acetylcholinesterase (AChE) inhibitory and mosquitocidal properties of isoxazol-3-yl dimethylcarbamates (15), and the corresponding 3-oxoisoxazole-2(3H)-dimethylcarboxamide isomers (14). In both series, compounds were found with excellent contact toxicity to wild-type susceptible (G3) strain and multiply resistant (Akron) strain mosquitoes that carry the G119S resistance mutation of AChE. Compounds possessing good to excellent toxicity to Akron strain mosquitoes inhibit the G119S mutant of An. gambiae AChE (AgAChE) with ki values at least 10- to 600-fold higher than that of propoxur, a compound that does not kill Akron mosquitoes at the highest concentration tested. On average, inactivation of WT AgAChE by dimethylcarboxamides 14 was 10-20 fold faster than that of the corresponding isoxazol-3-yl dimethylcarbamates 15. X-ray crystallography of dimethylcarboxamide 14d provided insight into that reactivity, a finding that may explain the inhibitory power of structurally-related inhibitors of hormone-sensitive lipase. Finally, human/An. gambiae AChE inhibition selectivities of these compounds were low, suggesting the need for additional structural modification.

ORGANOCOPPER COMPLEX, ORGANOCOPPER COMPLEX SOLUTION, COPPER OXIDE THIN FILM, METHOD FOR PRODUCING COPPER OXIDE THIN FILM, AND COMPOUND

Provided are: an organocopper complex having a structure represented by general formula (1); a copper oxide thin film comprising the organocopper complex; a method for producing the copper oxide thin film; and a compound constituting the organocopper comp

A novel method for the one-pot five-component synthesis of highly functionalized pyranopyrazoles catalyzed by CuI nanoparticles

A novel one-pot, five-component reaction for the synthesis of highly functionalized pyranopyrazoles from acid chlorides, Meldrum's acid, hydrazine hydrate, aromatic aldehydes and malononitrile in the presence of catalytic amount of CuI nanoparticles in aq