3442-15-7

Usage

Uses

Used in Pharmaceutical Synthesis:
Chalcone is utilized as a key intermediate in the synthesis of various pharmaceutical drugs. Its chemical structure allows for the creation of a wide range of bioactive compounds, contributing to the development of new medications for different health conditions.
Used in Medicinal Applications:
Chalcone serves as a therapeutic agent for treating a spectrum of diseases, including cancer, diabetes, and neurodegenerative disorders. Its multifaceted properties enable it to target various biological pathways and mechanisms involved in these conditions, offering potential health benefits.
Used in the Chemical Industry:
As a chemical intermediate, chalcone is employed in the production of other compounds, highlighting its versatility and importance in the chemical industry.
Used as a Natural Dye:
Chalcone's yellow crystalline nature makes it a candidate for use as a natural dye in various applications, such as in the textile or cosmetic industries, where there is a growing demand for eco-friendly and sustainable colorants.
Used as a Fluorescent Probe in Biological Imaging:
Chalcone's potential as a fluorescent probe allows it to be used in biological imaging, where it can help visualize cellular and molecular processes, contributing to advancements in life sciences research.

InChI:InChI=1/C16H14O2/c17-15(11-13-7-3-1-4-8-13)12-16(18)14-9-5-2-6-10-14/h1-10,12,18H,11H2/b16-12-

Upstream product

• 855378-01-7 3-methoxy-1,4-diphenyl-but-2ξ-en-1-one 
• 101-97-3 Ethyl 2-phenylethanoate 
• 98-86-2 acetophenone 
• 27735-65-5 2-(dimethyl-λ4-sulfanylidene)-1,4-diphenyl-butane-1,3-dione 
• 122-78-1 phenylacetaldehyde 
• 3282-32-4 2-diazo-acetophenone 
• 70-11-1 α-bromoacetophenone 
• 103-80-0 phenylacetyl chloride 
• 158392-63-3 4-bromo-3-hydroxy-1,3-diphenylbutan-1-one 
• 4636-16-2 iodoacetophenone 
• 89036-90-8 2-Methoxy-1-phenyl-2-phenylsulfanyl-ethanol 
• 89036-99-7 Acetic acid 2-methoxy-1-phenyl-2-phenylsulfanyl-ethyl ester 
• 101-41-7 benzeneacetic acid methyl ester 
• 140-29-4 phenylacetonitrile 

Downstream Products

• 952-06-7 deoxybenzoin oxime 
• 18753-56-5 3-Phenyl-5-(phenylmethyl)isoxazole 
• 955-10-2 3-phenylcumarin 
• 21917-99-7 3-benzyl-5-phenyl-1H-pyrazole 
• 499240-97-0 3-[(4-methoxybenzyl)amino]-1,4-diphenylbut-2-en-1-one 
• 499240-96-9 3-(benzylamino)-1,4-diphenylbut-2-en-1-one 
• 81385-87-7 2-methyl-1,4-diphenyl-1,3-butanedione 

Relevant academic research and scientific papers

Variations in the blaise reaction: Conceptually new synthesis of 3-amino enones and 1,3-diketones

Organic compounds with 3-amino enone or 1,3-diketone functional groups are extremely important, as they can be converted into a plethora of heterocyclic or carbocyclic compounds, or can be used as ligands in metal complexes. We have achieved a new, easy, straightforward and convenient synthesis of 3-amino enones and 1,3-diketones starting from aryl/heteroaryl/alkyl nitriles and 1-aryl/alkyl 2-bromoethanones. The reaction is a variation of the classical Blaise reaction, and it works with zinc and trimethylsilyl chloride as an activator. By running the hydrolysis of the reaction intermediate with HCl (3 N aq.) at 0-30 °C or at 100 °C, it is possible to form either 3-amino enones or 1,3-diketones, respectively. The newly developed method was used for the synthesis of avobenzone, an ingredient of sun-screen lotions. Furthermore, an easy synthesis of (Z)-3-amino-1-[4-(tertbutyl) phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one, with UV/Vis absorption characteristics similar to those of avobenzone, was also achieved.

Et2Zn-mediated rearrangement of bromohydrins

(Chemical Equation Presented) A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH 2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.

Synthesis and evaluation of estrogen agonism of diaryl 4,5- dihydroisoxazoles, 3-hydroxyketones, 3-methoxyketones, and 1,3-diketones: A compound set forming a 4D molecular library

In this paper, the preparation and systematic evaluation of estrogen receptor α (ERα) and estrogen receptor β (ERβ) activities of some diaryl-1,3-diones and their synthetic intermediates, diaryl-4,5-dihydroisoxazoles, diaryl-3-hydroxyketones, diaryl-3-met

Facile and straightforward method leading to substituted 4-amino-1-arylpyrazoles

A new method for the synthesis of substituted 4-amino-l-arylpyrazoles is described, starting from β-enaminones and variously substituted benzenediazonium tetrafluoroborates. The reaction proceeds under mild conditions, is very simple to perform, and is applicable to a relatively wide range of substituents, both at the β-enaminone and diazonium salt starting materials.

Zinc-mediated C-C bond sigmatropic rearrangement: A new and efficient methodology for the synthesis of β-diketones

(Chemical Equation Presented) A new and efficient methodology has been developed for the synthesis of β-diketones from aromatic α-bromo ketones in the presence of Furukawa reagent under mild conditions. The present transformation is proposed to proceed via a Reformatsky-type reaction of α-bromo ketones, followed by C-C bond sigmatropic rearrangement of the aldolate intermediate to give β-diketones in moderate to good isolated yields, while aliphatic α-bromomethyl ketones resulted in the formation of 2,4-disubstituted furans or cis-1,2-disubstituted cyclopropanols in moderate yields. The scope of this process was investigated, and a tentative mechanism was proposed.

The structure of pyrazoles in the solid state: A combined CPMAS, NMR, and crystallographic study

The structures of six N-unsubstituted pyrazoles, three already known and three newly synthesized, have been studied by a combination of X-ray crystallography, multinuclear NMR (solution and solid state), and density functional theory (DFT) calculations. I

Ion pair first and second acidities of some β-diketones and aggregation of their lithium and cesium enediolates in THF

Ion pair pK values were measured for three β-diketones in THF, 1-3, with lithium and cesium counterions. The results showed variations with concentration indicative of aggregation of the metal enolates to dimers. Similarly, ion pair pK values could be det

Enantioselective borohydride reduction catalyzed by optically active cobalt complexes

The highly enantioselective borohydride reduction of aromatic ketones or imines to the corresponding alcohols was developed in the presence of a catalytic amount of an optically active cobalt(II) complex catalyst. This enantioselective reduction is carried out using a precisely premodified borohydride with alcohols such as tetrahydrofurfuryl alcohol, ethanol and methanol. High optical yields are obtained by choosing the appropriate alcohol as modifiers and a suitable β-ketoiminato ligand of the catalyst. The enantioselective borohydride reduction has been successfully applied to the preparation of optically active 1,3-diols, the stereoselective reduction of diacylferrocenes, and dynamic and/or kinetic resolution of 1,3-dicarbonyl compounds.

A novel synthesis of 1,3-diketones by reaction of an α-bromoketone with acyl chlorides promoted by gallium triiodide

Promoted by gallium triiodide, an α-bromoketone, bromomethyl phenyl ketone, is treated with acyl chlorides to synthesize 1,3-diketones in good yields under mild and neutral conditions.

Process for the preparation of linear 1,3-diketones

There is disclosed a process for the preparation of 1,3-diketones of formula I STR1 wherein R1 and R2 are each independently of the other C1 -C20 alkyl, phenyl or phenyl which is substituted by halogen, hydroxy, NO2, C1 -C4 alkyl and/or C1 -C4 alkoxy, C7 -C9 phenylalkyl or a radical of formula II wherein A is C1 -C12 alkylene, phenylene or phenylene which is substituted by halogen, hydroxy, NO2, C1 -C4 alkyl and/or C1 -C4 alkoxy, or is C1 -C12 alkylene which is substituted by hydroxy, halogen and/or alkoxy, X is oxygen or sulfur, and R4 is hydrogen, C1 -C18 alkyl, phenyl or phenyl which is substituted by halogen, hydroxy, C1 -C4 alkyl, NO2 and/or C1 -C4 alkoxy, or is C7 -C9 phenylalkyl, and R3 is hydrogen, C1 -C20 alkyl, phenyl or phenyl which is substituted by halogen, hydroxy, C1 -C4 alkyl, NO2 and/or C1 -C4 alkoxy, or is C7 -C9 phenylalkyl. The process comprises carrying out a Claisen condensation of a ketone of formula III STR2 and an ester of formula IV STR3 wherein R5 is C1 -C5 alkyl, phenyl or phenyl which is substituted by halogen, C1 -C4 alkyl or hydroxy, the reaction being carried out with the base used as catalyst, a hydride of an alkali metal or alkaline earth metal or an alcoholate of C1 -C5 alkali metal or C1 -C5 alkaline earth metal, in a mixture of dimethyl sulfoxide and at least one organic solvent which is inert under the reaction conditions.