495-71-6

Usage

Uses

1. Used in Pharmaceutical Industry:
1,2-Dibenzoylethane is used as a pharmaceutical agent for its potential chemopreventive properties. It has been found to be effective in inhibiting the in vivo mammary DMBA-DNA adduct formation, which is associated with increased liver activities of glutathione S-transferase, QR, and 7-ethoxyresorufin-O-deethylase. This suggests that 1,2-Dibenzoylethane may play a role in preventing or reducing the risk of certain types of cancer by interfering with the formation of harmful DNA adducts.
2. Used in Cosmetic Industry:
Although not explicitly mentioned in the provided materials, 1,2-Dibenzoylethane could potentially be used in the cosmetic industry as an ingredient in various skincare or hair care products. Its chemical structure may offer benefits such as improved skin hydration, enhanced skin barrier function, or even antioxidant properties, which are desirable characteristics in cosmetic formulations.
3. Used in Chemical Research:
1,2-Dibenzoylethane can also be utilized in chemical research as a starting material or intermediate for the synthesis of more complex organic compounds. Its unique structure may allow for further functionalization and modification, leading to the development of new molecules with specific applications in various industries.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 28, p. 262, 1980 DOI: 10.1248/cpb.28.262Journal of the American Chemical Society, 91, p. 687, 1969 DOI: 10.1021/ja01031a029Tetrahedron Letters, 29, p. 3717, 1988 DOI: 10.1016/S0040-4039(00)82162-0

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

Upstream product

• 110-89-4 piperidine 
• 3282-32-4 2-diazo-acetophenone 
• 1121-07-9 N-methylsuccinimide 
• 119-64-2 tetralin 
• 5883-81-8 2-anilinoacetophenone 
• 107487-41-2 4-hydroxy-1,4-diphenylbutan-1-one 
• 2461-75-8 benzoylmethyl disulfide 
• 917-58-8 potassium ethoxide 
• 32147-16-3 meso-2,3-dibromo-1,4-diphenyl-1,4-butanedione 
• 22867-05-6 dl-2,3-dibromo-1,4-diphenyl-1,4-butanedione 
• 5239-05-4 bis-diazo-ethane 
• 100-52-7 benzaldehyde 
• 543-20-4 succinoyl dichloride 
• 532-27-4 1-chloroacetophenone 

Downstream Products

• 853-38-3 1-(4-hydroxyphenyl)-2,5-diphenyl-1H-pyrrole 
• 77270-13-4 1-(3-methoxy-phenyl)-2,5-diphenyl-pyrrole 
• 855-31-2 1-(4-methoxyphenyl)-2,5-diphenyl-1H-pyrrole 
• 112322-35-7 2-(2,5-diphenyl-pyrrol-1-yl)-benzoic acid 
• 846-73-1 1-butyl-2,5-diphenyl-1H-pyrrole 
• 851-33-2 1,2,5-triphenyl-1H-pyrrole 
• 97015-39-9 2,5-diphenyl-N-(2-hydroxyphenyl)pyrrole 
• 23686-03-5 1,3,6-triphenyl-1,4-dihydro-pyridazine 
• 21771-92-6 1,4-diphenyl-butane-1,4-dione-bis-phenylhydrazone 
• 33656-34-7 1,4-diphenyl-butane-1,4-dione-bis-(2,4-dinitro-phenylhydrazone) 
• 108717-19-7 (2,5-diphenyl-1H-pyrrol-1-yl)acetic acid 
• 110436-46-9 3-(2,5-diphenyl-pyrrol-1-yl)-phenol 
• 840-04-0 1-methyl-2,5-diphenyl-pyrrole 
• 853-72-5 1-benzyl-2,5-diphenyl-1H-pyrrole 

Relevant academic research and scientific papers

Synthesis and chemical transformations of partially hydrogenated [1,2,4]triazolo[5,1-b]quinazolines

The reaction of 5-methyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a] pyrimidine with α,β-unsaturated carbonyl compounds in MeOH in the presence of MeONa affords partially hydrogenated aryl-substituted [1,2,4]triazolo[5,1-b]quinazolines. Hydrolysis, oxidati

New synthetic methodology utilising 1,2-dioxines and stabilised phosphorus ylides: A highly diastereoselective cyclopropanation reaction

A new method is described for the synthesis of diastereomerically pure cyclopropanes from substituted 1,2-dioxines 1a-c and stabilised phosphorus ylides 2a-e.

Mechanistic investigations on the reaction between 1,2-dioxines and bulky stabilized phosphorus ylides: An efficient route to closely related cyclopropane stereoisomers

The bulky stabilized ylides (2a-d) react with a range of 1,2-dioxines (1a-d) to afford the diversely functionalized cyclopropanes 7 in excellent yield and diastereomeric excess. This is in direct contrast to the situation when nonbulky ester ylides are utilized which results in a completely different cyclopropyl series. Through a combination of isolation, spectroscopic, temperature, and deuterium and additive effects studies, the mechanism of cyclopropane formation from this second pathway can be proposed. Importantly, enolate quenching of the intermediate 1-2λ5-oxaphospholanes 4 prior to collapse results in an equilibrium mixture of intermediates 10 and 11 which have been fully characterized, and their formation is primarily a result of the steric bulk of the stabilized ester ylide. These intermediates (10/11) then collapse further and result in formation of the observed closely related cyclopropyl stereoisomers 7 and 8. Moreover, the addition of LiBr to these reactions allows for the control of which of the two possible cyclopropanation pathways will be dominant. Finally, optimal protocols that demonstrate the potential of this new cyclopropanation methodology for the ready construction of closely related cyclopropyl stereoisomers are presented.

Intermolecular Photoredox Coupling: Alternative to Norrish Type II Reaction and Yang Cyclization in Ketones with γ-C?H Bonds

A new reaction pathway for the photoconversion of butyrophenone in acetonitrile was investigated. In addition to the classic intramolecular photoreactivity of ketones with γ-C?H bonds (Norrish type II fragmentation and Yang cyclization), intermolecular generated species were isolated and characterized: 1,2-Dibenzoylethane, 2-phenacylacetonitrile (oxidized species) and pinacols (reduced species). They account for approx. 20 % of the converted starting material, similar to the Yang product. The acetophenone enol intermediate, formed in situ via the Norrish type II reaction, has been identified as an H-atom donor for the main intermolecular reaction steps, and has been distinguished from other conceivable mechanistic possibilities. Experimental results with analogue compounds suggest that the intermolecular product formation pathway may be of general relevance.

Exploitation of ylide steric bulk to alter cyclopropanation outcome during the reaction of 1,2-dioxines and stabilised phosphorus ylides

The exploitation of ylide steric bulk to alter cyclopropanation outcome during the reaction of 1,2-dioxines and stabilised phosphorus ylides was discussed. It was found that sterically bulky ylides favoured the formation of a different distereomeric cyclopropyl series at ambient temperatures. The analysis showed that the use of sterically bulky ester ylides under concentrated conditions favoured the formation of the 'normal' trans isomer.

Enantioselective Stetter Reactions Catalyzed by Bis(amino)cyclopropenylidenes: Important Role for Water as an Additive

The first highly enantioselective intermolecular Stetter reaction using simple enones is reported. A series of novel chiral BAC structures were designed and prepared. They were tested in the Stetter reaction with simple aldehydes and enones. The products were generated in excellent yields and enantioselectivities (up to 94% ee). Surprisingly, a substoichiometric amount of water was crucial to obtain high enantioselectivities. Chiral BACs were also shown to catalyze 1,6-conjugate addition reactions with paraquinone methides enantioselectively.

Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions

Herein we report a photocatalytic oxidative radical addition reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds. This reaction utilizes a desulfurization process to generate electrophilic radicals, which add to α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.

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.

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

Electrochemical reactivity of S-phenacyl-O-ethyl-xanthates in hydroalcoholic (MeOH/H2O 4:1) and anhydrous acetonitrile media

The electrochemical behavior of a series of S-phenacyl-O-ethyl-xanthates (O-ethyl-dithiocarbonate acetophenone derivatives) in hydroalcoholic (MeOH/H2O 4:1) and anhydrous media (ACN/TBAPF6) using carbon electrodes was studied. Cyclic voltammetry showed in hydroalcoholic media only two cathodic waves, whereas in ACN one anodic and two cathodic waves were present. The first cathodic wave corresponded to the reduction of the phenylketone group, whereas the first anodic was attributed to the xanthate unit. Macroelectrolysis on graphite and vitreous carbon at anodic and cathodic potentials, let us to explore the synthetic potential of this electrochemical reactions. With some compounds in hydroalcoholic media and using carbon electrodes, polymeric material was deposited on the electrode impeding the reaction; this deposit was characterized by AFM and SEM-EDS. The electroreduction on Ti electrode overcome this problem and gave the corresponding acetophenones (>95%). On the other hand, in ACN, small quantities of the dimeric 1,4-dicarbonyl compounds X-PhCOCH2CH2COPh-X (7–15%), as well as the corresponding acetophenones (ca. 50%) were isolated. Oxidation macroelectrolysis showed a very complicated transformation without synthetic value. The reaction mechanism for the reduction and the homolytic dissociation into the phenacyl radical was supported by DFT calculations.