58940-87-7

Usage

Classification

Pyrimidine derivative

Biological Significance

Integral part of nucleotide bases in DNA and RNA

Role in Genetic Coding

Essential for genetic coding and decoding processes

Hydrogen Bonding

Forms hydrogen bonds with guanine in DNA, contributing to stability of double helix structure
Two phenyl groups
Four-carbon chain
Amino group
Ketone group

Applications

Used in organic synthesis
Formation of various pharmaceuticals and organic compounds

Characteristic Properties

Aromaticity due to phenyl groups
Presence of amino and ketone functional groups
Conjugated system in the molecule

Functional Groups

Amino group ($-NH2$)
Ketone group ($-C=O$)

Molecular Weight

Approximately 111.1 g/mol

Upstream product

• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 
• 36744-90-8 S,S-Diphenylsulfilimine 
• 959-27-3 (Z)-1,4-diphenylbut-2-ene-1,4-dione 
• 65218-88-4 (+)-(R)-o-methoxyphenylphenyl free sulfimide 
• 613-90-1 benzoyl cyanide 
• 120-46-7 1,3-diphenylpropanedione 
• 70-11-1 α-bromoacetophenone 
• 1816-88-2 2-azido-1-phenylethan-1-one 
• 16883-69-5 N-phenacylpyridinium bromide 
• 93-91-4 1-phenylbutan-1,3-dione 

Relevant academic research and scientific papers

An efficient microwave accelerated three component reaction of phenacyl azides and pyridinium phenacyl salts: A facile greener approach to 2-amino-2-ene-1,4-diones/pyrrolidin-2-ones

A mild and efficient base promoted, microwave assisted, green synthesis of 2-amino-2-ene-1,4-diones has been described by the decomposition of phenacyl azides followed by treatment with pyridinium salts of phenacyl bromides in aqueous media. A diverse range of substrates bearing electron-releasing and electron-withdrawing substituents were well tolerated and delivered corresponding 2-amino-2-ene-1,4-diones in good yields. Synthesized 2-amino-2-ene-1,4-diones have been further explored in the synthesis of various substituted 4-hydroxypyrrolidin-2-ones.

EtOH/Ba(OH)2 triggers self-condensation of (E)-1,4-diaryl-2- butene-1,4-diones to cyclopentanol derivatives

Several stereo-defined penta-substituted cyclopentanols were synthesized from EtOH/Ba(OH)2-induced self-condensation of (E)-1,4-diaryl-2- butene-1,4-diones formed via domino pathways. Copyright Taylor & Francis, Inc.

Tin(IV) chloride-promoted versus Metal β-carbonylenolate-catalysed Reactions of β-Dicarbonyls with Nitriles

β-Ketoesters (2) and β-diesters (3) react with electrophilically activated nitriles, such as trichloroacetonitrile, ethyl cyanoformate and benzoyl cyanide and with non activated nitriles, such as acetonitrile, propiononitrile, benzyl cyanide, benzonitrile

ONE STEP SYNTHESIS OF AZIRIDINES BY THE MICHAEL TYPE ADDITION OF FREE SULFIMIDES

The Michael type additions of diphenyl N-unsubstituted sulfimide (free sulfimide) to various electrophilic olefins were carried out.The reaction with cis- and trans-dibenzoylethylene, dimethylfumarate, dimethylmaleate, benzalacetophenone and benzalacetone gave mainly the corresponding trans-2-acylaziridines and trans-enaminoketones.However, phenyl vinyl sulfone or acrylonitrile afforded not the corresponding aziridine but diphenyl-N-2-cyano or N-2-phenylsulfonylethylsulfimide, a simple Michael adduct.When optically active (+)-(R)-o-methoxyphenylphenyl free sulfimide was treated with such an α,β-unsaturated carbonyl compound as benzalacetophenone, an optically active 2-acylaziridine, i.e., (-)-trans-2-benzoyl-3-phenylaziridine was obtained in ca 30percent optical purity and its absolute configuration was assigned as (2R,3S) upon chemical transformation to the configurationally known 2-phenyl-2-benzoylamino-1-ethanol or by comparing its CD spectrum with that of (1R,2R)-1-phenyl-2-benzoyl-cyclopropane.Meanwhile, (-)-(S)-o-methoxyphenylphenyl free sulfimide was found to react with benzalacetophenone to afford (+)-trans-2-benzoyl-3-phenylaziridine of 25percent optical purity.Effects of solvent and temperature on both the distribution of the products ratio and the optical yield were examined.