959-27-3

Usage

Uses

Used in Medicinal Chemistry:
Chalcone is used as a starting material for the synthesis of various biologically active compounds, such as flavonoids, which are known for their antioxidant, anti-inflammatory, and anticancer properties. This application is due to chalcone's ability to serve as a versatile building block in the development of pharmaceuticals.
Used in the Textile Industry:
Chalcone is used as a dye in the textile industry, taking advantage of its fluorescent properties to create vibrant colors in fabrics.
Used in Optoelectronic Devices:
Chalcone has potential applications in the development of organic light-emitting diodes (OLEDs) and other optoelectronic devices, leveraging its fluorescent characteristics to enhance the performance of these technologies.

Upstream product

• 955-83-9 2,5-diphenylfuran 
• 67-66-3 chloroform 
• 546-67-8 lead(IV) tetraacetate 
• 23637-57-2 (Z)-1,4-diphenylbut-2-ene-1,4-diol 
• 532-27-4 1-chloroacetophenone 
• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 
• 838-40-4 2,5-diphenyl-1H-pyrrole 
• 1445-78-9 2,5-Diphenyl-thiophene 
• 5369-55-1 2,4-diphenylfuran 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 67-56-1 methanol 
• 10028-15-6 ozone 
• 67-64-1 acetone 

Downstream Products

• 160620-54-2 3,4-dibenzoyl-4,5-dihydro-1H-pyrazole 
• 975-70-2 (6-benzoyl-3,4-dimethylcyclohex-3-enyl)(phenyl)methanone 
• 74007-33-3 2endo.3endo-dibenzoyl-norbornene-⁽⁵⁾ 
• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 
• 107538-22-7 meso-1.4-diphenyl-butene-(2t)-diol-(1.4) 
• 36771-13-8 (5exo,6exo-dibenzoyl-4-ethoxy-7-oxa-2-aza-bicyclo[2.2.1]hept-3-ylidene)-acetic acid ethyl ester 
• 104312-06-3 (R)-2-((R)-1-Hydroxy-3-phenyl-propyl)-1,4-diphenyl-butane-1,4-dione 
• 104312-06-3 (R)-2-((S)-1-Hydroxy-3-phenyl-propyl)-1,4-diphenyl-butane-1,4-dione 
• 140410-19-1 C₂₈H₃₃NO₃ 
• 570391-52-5 1,4-diphenyl-2-(2-oxocyclopentyl)-1,4-butanedione 
• 140410-16-8 C₂₅H₂₇NO₃ 
• 38172-24-6 C₂₂H₃₀O₂Si₂ 
• 92670-73-0 2-<1-(3,5-diphenylpyrazolyl)>-1,4-diphenylbutane-1,4-dione 
• 139-66-2 diphenyl sulfide 

Relevant academic research and scientific papers

An Efficient Regeneration of Singlet Oxygen from 2,5-Diphenylfuran Endoperoxide Produced by a Dye-Sensitized Oxygenation

The maximum quantum yield of 4.5 was evaluated from the kinetic analysis for the Methylene Blue-sensitized oxygenation of 2,5-diphenylfuran, and the contribution of a chain process to produce the furan endoperoxide was suggested.After the photoreaction, t

Ring Opening of π-Delocalized 2,5-Diphenyltellurophene by Chemical or Self-Sensitized Aerobic Photooxidation

We report the self-sensitized aerobic photooxidation of 2,5-diphenyltellurophene (PT). Irradiation of PT induces rapid intersystem crossing to the triplet excited state, which undergoes energy transfer to oxygen to form singlet oxygen. Reaction of the heterocycle with singlet oxygen was found to occur at the carbon framework through a 1,4-cycloaddition reaction rather than at tellurium to form the Te(IV) telluroxide, as is commonly observed for other tellurium-containing heterocycles. This leads to oxidative ring-opening of the tellurophene to form (Z)-1,4-diphenylbut-2-ene-1,4-dione ((Z)-ED) with extrusion of TeO2. In attempts to study the formation of the Te(IV) telluroxide and Te(VI) tellurone by chemical oxidation with m-chloroperoxybenzoic acid (mCPBA), we discovered that PT undergoes an oxidative ring-opening reaction to the same ene-dione product after reaction with 4 equiv of mCPBA. Extrusion of TeO2 was also observed in this case. This ring-opening reaction was studied in detail by NMR spectroscopy, GC-MS, and density functional theory calculations.

Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones

An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete E-stereoselectivity. The reaction mechanism has been investigated through deuterium-labeling experiments and intermediate experiments.

Stereoselective Synthesis of cis-2-Ene-1,4-diones via Aerobic Oxidation of Substituted Furans Catalyzed by ABNO/HNO3

We report a highly efficient and selective catalytic system, ABNO (9-azabicyclo-[3.3.1]nonane N-oxyl)/HNO3, for the aerobic oxidation of substituted furans to cis-2-ene-1,4-diones under mild reaction conditions using oxygen as the oxidant. The catalyst system is amenable to various substituted (mon-, di-, and tri-) furans and tolerates diverse functional groups, including cyano, nitro, naphthyl, ketone, ester, heterocycle, and even formyl groups. Based on the control and 18O-labeling experiments, the possible mechanism of the oxidation is proposed.

Oxidative cleavage of 1,3-diaryl/(heteroaryl)benzo[c]furans into 1,2-diaroyl/(heteroaroyl)benzenes using selenium dioxide

Reaction of 1,3-disubstituted isobenzofurans (IBFs) with selenium dioxide in tetrahydrofuran (THF) at room temperature led to the formation of 1,2-diaroyl/(heteroaroyl)benzenes in good to excellent yields.

Visible-light-mediated oxidative dimerization of arylalkynes in the open air: Stereoselective synthesis of (Z)-1,4-enediones

An organic photoredox catalytic one-pot protocol is developed for the highly stereoselective synthesis of (Z)-1,4-enediones. The reaction starts directly from alkyne precursors, using 4-(4-cyanophenyl)-2,6-diphenylpyrylium tetrafluoroborate (CN-TPT) as an efficient photosensitizer and dioxygen in the air as a green oxidant. A Csp-Csp oxidative coupling/[4 + 2] cyclization (with dioxygen)/fragmentive isomerization cascade mechanism was proposed. The predominant formation of (Z)-1,4-enediones is attributed to the efficient visible-light illumination from blue LEDs, along with possible energy transfer from the photosensitizer CN-TPT to the E-isomers.

Synthesis of Aromatic Retinoids and Curcuminoids and Evaluation of their Antiproliferative, Antiradical, and Anti-inflammatory Activities

Natural retinoids and curcuminoids are known for their broad spectrum of biological properties, such as antioxidant, anti-inflammatory, antitumor, and so forth. In this work, a convenient synthesis of aromatic retinoids and curcuminoids from vinyl or allyl ketones, and the corresponding alcohols, using olefin metathesis as a key reaction, was elaborated. The best yields and diastereoselectivities were obtained from allylic or homoallylic alcohols by employing the two-step cross-metathesis/oxidation procedure. The synthesized analogues were tested for their antiproliferative activity on human cancer cell lines of various origin (leukemia CEM, adenocarcinoma MCF7, cervical carcinoma HeLa) as well as for their antioxidant and anti-inflammatory activity in vitro. All examined derivatives exhibited strong anti-inflammatory activity in vitro without affecting cell viability. They also showed strong cytotoxicity against leukemia cell line CEM, except for 18 and 35. The antioxidant activity of the tested compounds was rather weak.

Enaminones via ruthenium-catalyzed coupling of thioamides and α-diazocarbonyl compounds

Enaminones can be prepared via the Rh2(OAc)4- catalyzed coupling of α-diazocarbonyl compounds with thioamides. However, rhodium is the most expensive and least abundant among the dominant precious metals used for catalysis. Furthermore, a very limited substrate scope is known for the intermolecular rhodium catalyzed coupling reaction. Therefore, there is a need to find a more economical catalyst substitute with a broad substrate scope. In this paper, we describe the use of Ru(II) catalysts for the synthesis of enaminones. The reaction can be performed efficiently with the Grubbs first-generation catalyst or [(Ph)3P]3RuCl2 in a sealed tube. Both catalysts are much less expensive than Rh 2(OAc)4. Secondary and tertiary thioamides, when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, and α-diazomonoketones give enaminones. Primary thioamides give thiazole derivatives when reacted with α-diazomonoketones. However, with other diazo compounds, primary thioamides also give enaminones. All enaminones are obtained in good yields and with good diastereoselectivity. Accordingly, the method described in this paper is an efficient and economical alternative to the Rh2(OAc)4-catalyzed coupling process.

ZnII- and AuI-catalyzed regioselective hydrative oxidations of 3-En-1-ynes with selectfluor: Realization of 1,4-dioxo and 1,4-oxohydroxy functionalizations

Catalytic 1,4-dioxo functionalizations of 3-en-1-ynes to (Z)- and (E)-2-en-1,4-dicarbonyl compounds are described. This regioselective difunctionalization was achieved in one-pot operation through initial alkyne hydration followed by in situ Selectfluor oxidation. The presence of pyridine alters the reaction chemoselectivity to give 4-hydroxy-2-en-1-carbonyl products instead. A cooperative action of pyridine and ZnII assists the hydrolysis of key oxonium intermediate.

A highly tunable stereoselective dimerization of methyl ketone: Efficient synthesis of e - And Z-1,4-enediones

A new method for the tunable synthesis of 1,4-enedione directly from aromatic methyl ketone is described. This tandem reaction enables the construction of symmetric and unsymmetric 1,4-enediones with complete E-selectivity. Moreover, the resulting E-1,4-enedione could be transformed into a Z-isomer by irradiation with 23 W of white light.