959-28-4

Usage

Uses

Used in Pharmaceutical Industry:
TRANS-1,2-DIBENZOYLETHYLENE is used as a key intermediate for the synthesis of biologically potent heterocycles with antimicrobial properties, contributing to the development of new antimicrobial agents to combat drug-resistant infections.
Used in Chemical Synthesis:
TRANS-1,2-DIBENZOYLETHYLENE is used as a chemical intermediate in the synthesis of various organic compounds, enabling the creation of a wide range of products with diverse applications in different industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 360, 1990 DOI: 10.1021/jo00288a066Journal of the American Chemical Society, 45, p. 1303, 1923 DOI: 10.1021/ja01658a026

Purification Methods

It crystallises from MeOH or EtOH as yellow needles [Koller et al. Helv Chim Acta 29 512 1946]. The dioxime has m 210-211o(dec) from AcOH. [IR: Kuhn et al. J Am Chem Soc 72 5058 1950, Yates J Am Chem Soc 74 5375 1952, Erickson et al. J Am Chem Soc 73 5301 1951, Beilstein 7 IV 2578.]

InChI:InChI=1/C16H12O2/c17-15(13-7-3-1-4-8-13)11-12-16(18)14-9-5-2-6-10-14/h1-12H/b12-11+

Upstream product

• 3282-32-4 2-diazo-acetophenone 
• 4440-99-7 1,4-diphenyl-2-hydroxy-1,4-butanedione 
• 108-24-7 acetic anhydride 
• 532-27-4 1-chloroacetophenone 
• 60-29-7 diethyl ether 
• 959-27-3 (Z)-1,4-diphenylbut-2-ene-1,4-dione 
• 121-44-8 triethylamine 
• 627-63-4 fumaryl dichloride 
• 71-43-2 benzene 
• 838-40-4 2,5-diphenyl-1H-pyrrole 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 98288-15-4 methyl 2-methoxycinnamate 
• 14275-61-7 (E)-1,2-bis(tri-n-butylstannyl)ethene 

Downstream Products

• 4441-00-3 dibenzoyl-N-morpholinoethane 
• 5336-77-6 2,3-di-morpholin-4-yl-1,4-diphenyl-butane-1,4-dione 
• 26454-88-6 1,4-diphenyl-2-(phenylamino) but-2-ene-1,4-dione 
• 74007-33-3 (+/-)-2endo.3exo-dibenzoyl-norbornene-⁽⁵⁾ 
• 102599-25-7 (+/-)-2r.3t-dibenzoyl-bicyclo[2.2.2]octene-⁽⁵⁾ 
• 860549-74-2 9,10-dibenzoyl-1,2,3,4,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene 
• 857580-26-8 2,3-dibenzoyl-benz[de]anthracen-7-one 
• 76118-48-4 2-(N,N-dimethylamino)-1,4-diphenyl-1,4-butanedione 
• 975-70-2 trans dibenzoyl-4,5 dimethyl-1,2 cyclohexene 
• 2461-81-6 3-benzoyl-1,5-diphenyl-pentane-1,5-dione 
• 22862-82-4 1.4-diphenyl-butene-(2t)-dione-(1.4)-dioxime 
• 495-71-6 phenacylacetophenone 
• 4915-93-9 C,C'-diphenyl-C,C'-[3-(3-phenyl-[1,2,4]oxadiazol-5-yl)-cyclopropane-1r,2t-diyl]-bis-methanone 
• 104312-09-6 (S)-2-((S)-Furan-2-yl-hydroxy-methyl)-1,4-diphenyl-butane-1,4-dione 

Relevant academic research and scientific papers

A Novel Synthesis of 4-Dioxy-2-enones from 1,3-Dienes using Pyridinium Dichromate-tert-Butyl Hydroperoxide

Treatment of 1,3-dienes with the pyridinium dichromate (PDC)-t-BuOOH reagent system leads directly to the formation of 4-tert-butyldioxy-2-enones in good yield under mild reaction conditions.

Visible-Light-Driven Z -Selective Reaction of Methyl Ketones with DMSO: A Mild Synthetic Approach to Methylthio-Substituted 1,4-Enedione Promoted by Selectfluor

Here we disclose a simple, visible-light-driven Z -selective synthesis of methylthio-substituted 1,4-enedione in a single step promoted by Selectfluor. Dimethyl sulfoxide is used as both the 'thio' source and the solvent. Molecular iodine and potassium persulfate are used as catalyst and oxidant, respectively. White light (CFL-30W) is used as the light source. The proposed mechanism involves a Kornblum reaction followed by aldol reaction.

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.

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.

Diastereoselective sp3-C–H Functionalization of Arylmethyl Ketones and Transformation of E- to Z-Products Through Photocatalysis

We have developed an efficient metal-free route for the synthesis of 1,4-enedione derivatives under microwave irradiation by reacting easily available arylmethylketones with DMSO or diphenyl sulfoxide in the presence of TBAI and persulfate. The reaction is very clean and completes within very short time. All the reagents and catalysts are cheap and environmentally benign. In addition, the E-isomer of the products can easily be transformed into the Z-isomer by using eosin Y photocatalyst under the irradiation of white CFL.

Synergistic Catalysis of Se and Cu for the Activation of α-H of Methyl Ketones with Molecular Oxygen/Alcohol to Produce α-Keto Acetals?

Selenium and copper synergistically catalyzed the oxidation/alkoxylation of methyl ketones to synthesize α-keto acetals directly. Using O2 as oxidant and alcohol as solvent and alkoxylation reagent, the reaction is practical from industrial viewpoint. Mechanistic studies revealed that copper promoted the oxidation of organoselenium intermediates with O2 to allow the key rearrangement and selenoxide syn-elimination regenerating the catalytically active organoselenium species.

Proton-Coupled Electron Transfer: Transition-Metal-Free Selective Reduction of Chalcones and Alkynes Using Xanthate/Formic Acid

Highly chemoselective reduction of α,β-unsaturated ketones to saturated ketones and stereoselective reduction of alkynes to (E)-alkenes has been developed under a transition-metal-free condition using a xanthate/formic acid mixture through proton-coupled electron transfer (PCET). Mechanistic experiments and DFT calculations support the possibility of a concerted proton electron-transfer (CPET) pathway. This Birch-type reduction demonstrates that a small nucleophilic organic molecule can be used as a single electron-transfer (SET) reducing agent with a proper proton source.

Direct Aerobic Oxidative Reactions of 2-Hydroxyacetophenones

Valuable and direct aerobic oxidation reactions of 2-hydroxyacetophenones were explored. The concept was based on the in situ treatment of small quantities of aerobically formed α-keto aldehydes that drove the reactions to the corresponding products. This new strategy was applied for a variety of oxidative reactions of 2-hydroxyacetophenones, and valuable products such as phthalides, quinoxalines, and α-keto amides were obtained in good to high yields.

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.

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.