115984-23-1

Basic information

• Product Name: (E)-1,3-dimethyl-5-(3-phenylallylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
• Synonyms: (E)-1,3-dimethyl-5-(3-phenylallylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
• CAS NO: 115984-23-1
• Molecular Formula: C₁₅H₁₄N₂O₃
• Molecular Weight: 270.28326
• Mol File: 115984-23-1.mol

Chemical Properties

• Melting Point: 204-206 °C
• Boiling Point: 413.2±48.0 °C(Predicted)
• Appearance: /
• Density: 1.324±0.06 g/cm3(Predicted)
• PKA: -2.19±0.20(Predicted)
• CAS DataBase Reference: (E)-1,3-dimethyl-5-(3-phenylallylidene)pyrimidine-2,4,6(1H,3H,5H)-trione(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1,3-dimethyl-5-(3-phenylallylidene)pyrimidine-2,4,6(1H,3H,5H)-trione(115984-23-1)
• EPA Substance Registry System: (E)-1,3-dimethyl-5-(3-phenylallylidene)pyrimidine-2,4,6(1H,3H,5H)-trione(115984-23-1)

Safety Data

• Hazardous Substances Data: 115984-23-1(Hazardous Substances Data)

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 100-52-7 benzaldehyde 

Downstream Products

• 115984-30-0 (1α,2α,3β,4β)-1,3-Bis(1,2,3,4,5,6-hexahydro-1,3-dimethyl-2,4,6-trioxo-5-pyrimidinylidenmethyl)-2,4-diphenylcyclobutan 
• 82657-34-9 1,3-dimethyl-5-(3-phenylpropyl)pyrimidine-2,4,6(1H,3H,5H)-trione 

Relevant articles and documents

Molecular recognition on functionalized self-assembled monolayers of alkanethiols on gold

A system for probing molecular recognition events at organic interfaces using fluorescent receptors is described. Receptors formed from the bis(2,6- diaminopyridine) amide of isophthalic acid are incorporated in mixed self- assembled monolayers (SAMs) of

Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes

A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.

SHIKIMATE PATHWAY INHIBITORS AND THE USE THEREOF

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The syntheses of a new class of barbiturate-based inhibitors for human and Escherichia Coli methionine aminopeptidase-1 (MetAP-1) are described. Some of the synthesized inhibitors show selective inhibition of the human enzyme with high potency.

Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates

Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate. If 5-benzylbarbiturate is the target product, then the first step includes the preparation of 5-benzylidene. Regardless of the nature of the first step, all reactions presented synthetic yields around 90% and isolation and purification involves only crystallization.

Reductive C-alkylation of barbituric acid derivatives with carbonyl compounds in the presence of platinum and palladium catalysts

Effective synthetic procedures for the preparation of mono- and di-C-alkylated barbituric acid derivatives through palladium and platinum catalytic hydrogenation of solutions of barbituric acids (unsubstituted, N-mono, and N,N′-disubstituted barbituric acids) and carbonyl compounds (aliphatic and aromatic aldehydes and ketones).

5-Arylidene 1,3-Dimethylbarbituric Acid Derivatives, Mild Organic Oxidants for Allylic and Benzylic Alcohols

Various 5-arylidene 1,3-dimethylbarbituric acid derivatives and closely related compounds were synthesized as models of redox coenzymes and used for oxidation of alcohols.Under mild neutral conditions, 5-arylidene 1,3-dimethylbarbituric acid derivatives, especially those having an electron-withdrawing group on the aromatic ring, effectively oxidized allylic and benzylic alcohols to the corresponding carbonyl compounds.The relationship between the oxidizing ability and the structure of the oxidant (coenzyme model) was investigated and it was found that the electron density on the carbon-carbon double bond is a critical factor for the oxidation.In the case of the deuterium-labeled compound, the observed value of normal and primary isotope effect was 3.3 and so it was concluded that mechanism of this oxidation mainly involves the hydride transfer from the alcohol.An electrochemical investigation was also carried out and the redox potentials of the coenzyme models, 5-arylidene 1,3-dimethylbarbituric acid derivatives and related compounds, were measured.Keywords - 5-arylidene 1,3-dimethylbarbituric acid; coenzyme model; oxidation; allylic alcohol; benzylic alcohol; oxidation mechanism; hydride transfer; primary isotope effect; cyclic voltammetry; redox potential

Photoreactions in Crystals with Ethenes: Selectivities and Crystal Engineering

Photoreactions in crystals of sterically hindered dimethylenecyclopentanones 1 and trimethylenecyclopentanes 4 lead to E/Z isomerizations and 1,5-H shifts.The stereochemical result of the photodimerization in the crystalline state of the heterostilbenes 6