5465-41-8

Usage

Uses

Used in Organic Synthesis:
(2E)-1,4-bis(4-methylphenyl)but-2-ene-1,4-dione is used as a building block in organic synthesis for the creation of various chemical compounds.
Used in Pharmaceutical Industry:
(2E)-1,4-bis(4-methylphenyl)but-2-ene-1,4-dione is used as a starting material or intermediate in the development of pharmaceutical products due to its potential applications in this field.
Used in Agricultural Industry:
(2E)-1,4-bis(4-methylphenyl)but-2-ene-1,4-dione may be utilized in the agricultural industry for the development of new agrochemicals or as a component in existing products.

Upstream product

• 122-00-9 para-methylacetophenone 
• 627-63-4 fumaryl dichloride 
• 108-88-3 toluene 
• 619-41-0 4-(bromoacetyl)toluene 
• 7647-01-0 hydrogenchloride 
• 42289-03-2 (Z)-1,4-Bis(4-methylphenyl)but-2-ene-1,4-dione 
• 64-19-7 acetic acid 
• 7726-95-6 bromine 
• 13145-56-7 1,4-bis(4-tolyl)butane-1,4-dione 
• 7446-08-4 selenium(IV) oxide 
• 64-17-5 ethanol 

Downstream Products

• 42289-03-2 (Z)-1,4-Bis(4-methylphenyl)but-2-ene-1,4-dione 
• 42289-06-5 meso-2.3-dibromo-1.4-di-p-tolyl-butanedione-(1.4) 
• 42289-06-5 racem.-2.3-dibromo-1.4-di-p-tolyl-butanedione-(1.4) 
• 21399-23-5 2,5-di(4-methylphenyl)-1H-pyrrole 
• 62422-95-1 1,3-di-p-tolylbenzo[c]furan 
• 1198095-41-8 2-(1,2-di(4-methylbenzoyl)ethyl)malononitrile 
• 130443-16-2 5,6-Dimethyl-1,3-di-p-tolyl-benzo[c]thiophene 
• 124740-32-5 1,2-dimethyl-4,5-di-p-toluoyl-benzene 
• 130443-06-0 5,6-dimethyl-1,3-di-p-tolyl-4,7-dihydro-isobenzofuran 
• 117845-65-5 [(1S,3S)-2-(4-Chloro-benzenesulfonyl)-3-(4-methyl-benzoyl)-cyclopropyl]-p-tolyl-methanone 
• 117845-66-6 [(1S,3S)-2-(4-Bromo-benzenesulfonyl)-3-(4-methyl-benzoyl)-cyclopropyl]-p-tolyl-methanone 
• 117845-64-4 [(1S,3S)-2-Benzenesulfonyl-3-(4-methyl-benzoyl)-cyclopropyl]-p-tolyl-methanone 
• 78830-56-5 [4-(4-Methyl-benzoyl)-2-(4-nitro-phenyl)-5-phenyl-2H-pyrazol-3-yl]-p-tolyl-methanone 
• 78830-46-3 [1-(4-Nitro-phenyl)-3-phenyl-1H-pyrazol-4-yl]-p-tolyl-methanone 

Relevant academic research and scientific papers

Visible-Light-Driven Stereoselective Annulation of Alkyl Anilines and Dibenzoylethylenes via Electron Donor-Acceptor Complexes

A catalyst-free, stereoselective visible-light-driven annulation reaction between alkenes and N,N-substituted dialkyl anilines for the synthesis of substituted tetrahydroquinolines is presented. The reaction is driven by the photoexcitation of an electron donor-acceptor (EDA) complex, and the resulting products are obtained in good to high yields with complete diastereoselectivity. Mechanistic rationale and photochemical characterization of the EDA-complex are provided.

Facile Synthesis of Enantiopure Sugar Alcohols: Asymmetric Hydrogenation and Dynamic Kinetic Resolution Combined

An unprecedented Ir/f-amphox-catalyzed asymmetric hydrogenation of racemic 2,3-syn-dihydroxy-1,4-diones is presented involving dynamic kinetic resolution, which produces (1R,2R,3R,4R)-tetraols. This protocol constitutes an efficient and straightforward approach to accessing sugar alcohols bearing four contiguous stereocenters. The strategy exhibits various advantages over existing methods, including excellent yields (up to 98 %), exceptional stereoselectivities (up to 99:1 dr, 99.9 % ee), operational simplicity and substrate generality. Moreover, the nature of the reaction was revealed as a stepwise transformation by in situ Fourier-transform infrared spectroscopy and isolation of intermediates.

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.

An Expedient, Direct, Three-Component Approach for the Synthesis of 4-Thioarylpyrroles

A three-component strategy for the synthesis of 4-thioarylpyrroles from 1,4-enediones, thiols, and ammonium formate in one-pot has been developed. The reaction proceeds through the sequential thiol-Michael/Paal-Knorr reaction of 1,4-enediones with the for

Asymmetric organocatalytic aza-michael reactions of isatin derivatives

Isatin was activated by derivatization to a Schiff base with aniline and used as an aza-Michael donor in organocatalytic asymmetric reactions with symmetric and nonsymmetric unsaturated 1,4-diketones. After hydrolysis (in situ), the N-substituted isatins were obtained in high yields (up to >95%) with high enantioselectivity (up to 95%).

Asymmetric diastereoselective synthesis of spirocyclopropane derivatives of oxindole

A new asymmetric organocatalytic synthesis of spirocyclopropane oxindoles has been developed. The method is based on the Michael addition of N-Boc-protected 3-chlorooxindole to unsaturated 1,4-dicarbonyl compounds, affording trans-substituted spirocyclopropane oxindole derivatives in high diastereo- and enantioselectivity. Copyright

Synthesis of (E)-1,4-enediones from α-halo ketones through a sodium sulfinate mediated reaction

We developed a mild and practical protocol for the synthesis of 1,4-enedione from α-halo ketones through a sodium sulfinate mediated reaction. This reaction enables the construction of symmetric and unsymmetric 1,4-enedione with complete E selectivity. Sodium 4-toluenesulfinate plays an important role in this reaction.

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.

Indirect regioselective heteroarylation of indoles through a Friedel-Crafts reaction with (E)-1,4-diaryl-2-buten-1,4-diones

A two-step synthesis of 3-heteroaryl indoles has been developed. The first step of the sequence involves a Friedel-Crafts alkylation of indoles with 1,4-diaryl-2-buten-1,4-diones to give the corresponding indoles bearing a 1,4-dicarbonyl moiety. The reaction is catalyzed by InCl3 and takes place with good yields. Cyclization of the diones under different Paal-Knorr conditions allows to prepare indoles substituted at the C3 position with 3-furanyl, 3-pyrrolyl- and 3-thienyl moieties.

Lewis acid-catalyzed one-pot, three-component route to chiral 3,3′-bipyrroles

(Chemical Equation Presented) 3,3′-Bipyrroles 3 could be synthesized using a double Michael addition reaction involving diaroyl acetylene 1 and the appropriate 1,3-dicarbonyls 2 using ammonium acetate as a nitrogen source. The axial chirality of bipyrrole was anticipated from the X-ray crystal structure and DFT calculations and confirmed by separating the racemates on a chiral column and subsequent CD spectra of the enantiomers. The absolute configuration of the enantiomers was achieved by theoretical CD spectra calculation using the ZINDO method.