79997-18-5

Usage

Class

1,2-diketone compounds

Usage

Commonly used as a ligand in coordination chemistry

Potential applications

Catalysis and organometallic chemistry

Structure

Central 1,2-ethanedione moiety with a 3,4-dimethoxyphenyl group and a phenyl group attached

Research fields

Organic and inorganic chemistry

Properties

Promising properties in various chemical reactions

Upstream product

• 67-56-1 methanol 
• 151-50-8 potassium cyanide 
• 100-52-7 benzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 136944-02-0 2-(3,4-Dimethoxy-phenyl)-2-methylsulfanyl-1-phenyl-ethanone 
• 91-16-7 1,2-dimethoxybenzene 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 1466-17-7 3,4-dimethoxystilbene 
• 5398-93-6 2-methylthio-1-phenyl-ethanone 
• 14755-55-6 α-benzoyl-α-(methylthio)methyl chloride 
• 103-82-2 phenylacetic acid 
• 3141-93-3 4',5'-dimethoxydeoxybenzoin 
• 103-80-0 phenylacetyl chloride 
• 3864-15-1 1-(3,4-Dimethoxyphenyl)-2-phenylethanol 

Downstream Products

• 1312205-71-2 3-(3,4-dimethoxyphenyl)-2,4,5-triphenylcyclopenta-2,4-dienone 

Relevant academic research and scientific papers

The Synthesis of Imidazo[1,2- f ]phenanthridines, Phenanthro-[9,10- d ]imidazoles, and Phenanthro[9′,10′:4,5]imidazo[1,2- f ]-phenanthridines via Intramolecular Oxidative Aromatic Coupling

A short and efficient access to phenanthro[9,10-d ]imidazoles, imidazo[1,2-f ]phenanthridines, and phenanthro[9′,10′:4,5]imidazo[1,2-f ]phenanthridines was achieved by the action of [bis(trifluoroacetoxy)iodo]benzene (PIFA) on properly substituted tetraaryla-imidazoles. By pre-installing suitable electron-donating groups, it is possible to control the site of intramolecular oxidative aromatic coupling. In particular, by placing 3,4-dimethoxyphenyl and 3-methoxyphenyl moieties in close proximity, it was possible to direct the reaction into forming two biaryl linkages leading eventually to the formation of phenanthro[9′,10′:4,5]imidazo[1,2- f ]phenanthridines. Starting from bis-aldehydes that are derivatives of thieno[3,2- b ]thiophene and fluorene enabled the synthesis of π-expanded imidazoles bearing 8-9 conjugated rings. By placing a dimethoxynaphthalene unit on the imidazole scaffold, we have directed the oxidative coupling reaction towards closing a five-membered ring with concomitant removal of methoxy group leading to formation of an α,β-unsaturated ketone. All resulting π-expanded imidazoles display blue emission, and the fluorescence quantum yields in some cases reaches 0.9.

One-pot cascade synthesis of α-diketones from aldehydes and ketones in water by using a bifunctional iron nanocomposite catalyst

A new methodology for the synthesis of α-diketones was reportedviaa one-pot cascade process from aldehydes and ketones catalyzed by a bifunctional iron nanocomposite using H2O2as a green oxidant in water. The one-pot strategy showed excellent catalytic stability, comprehensive suitability of substrates and important practical utility for directly synthesizing biologically active and medicinally valuable N-heterocyclesviaan intermittent process.

A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones

We herein report the fabrication of a bifunctional iron nanocomposite catalyst, in which two catalytically active sites of Fe-Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under mild reaction conditions. Furthermore, it could be easily recovered for successive recycling without appreciable loss of activity. Mechanistic studies disclose that the direct oxidation of alkenes proceeds via the formation of an epoxide as intermediate followed by either acid-catalyzed Meinwald rearrangement to give ketones with one carbon shorter or nucleophilic ring-opening to generate 1,2-diketones in a cascade manner. This study not only opens up a fancy pathway in the rational design of Fe-N-C catalysts but also offers a simple and efficient method for accessing industrially important ketones and 1,2-diketones from alkenes in a cost-effective and environmentally benign fashion.

An unusual chemoselective oxidation strategy by an unprecedented exploration of an electrophilic center of DMSO: A new facet to classical DMSO oxidation

A conceptually new dimethyl sulfoxide (DMSO) based oxidation process without the use of any activator has been demonstrated for the oxidation of active methylenes and benzhydrols. The developed protocol utilizes the electrophilic center of DMSO for oxidation, which was unexplored before. Mechanistic investigation has confirmed that the source of oxygen is DMSO.

Synthesis of 1,2-diketones from β-keto nitriles via a protection-oxidative-decyanation-deprotection protocol

A variety of 1,2-diketones were prepared from -keto nitriles via a three-step protocol including the protection of the ketones with methoxyamine, oxidative decyanation, and microwave-assisted deprotection in the final step. This approach provides a novel and efficient access to a wide scope of symmetric and unsymmetric 1,2-diketones using molecular oxygen as the oxidant in the decyanation process. Georg Thieme Verlag Stuttgart - New York.

Hexaphenylbenzene-based polymers of intrinsic microporosity

Microporous polymers derived from the 1,2- and 1,4-regioisomers of di(3′,4′-dihydroxyphenyl)tetraphenylbenzene have very different properties with the former being composed predominantly of cyclic oligomers whereas the latter is of high molar mass suitable for the formation of robust solvent-cast films of high gas permeability.

Synthesis of unsymmetrically substituted benzils via the Friedel-Crafts reaction of arenes with α-chloro-α-(methylthio)acetophenones

Lewis acid-promoted reactions of arenes with α-chloro-α-(methylthio)acetophenones gave the Friedel-Crafts reaction products, which were then treated with 3 molar eq of cupric chloride in aqueous acetone to afford the unsymmetrically substituted benzils.

The Photochemistry of the Host-Guest Complex. V. The Effect of the Sodium Ion on the Photoreaction of Benzil Derivatives with a Crown Ether Moiety

The photolysis of 4'-(2-phenyl-1,2-dioxoethyl)benzo-15-crown-5 in benzene containing 1-dodecanethiol gives benzaldehyde and 4'-formylbenzo-15-crown-5.The formation of the aldehydes was inhibited by the sodium ion, whereas the photolysys of 1-(3,4-dimethoxyphenyl)-2-phenylethanedione was not inhibited by the sodium ion.This inhibition must be due to the decrease in the formation of benzoyl radicals from the triplet excited state of the crown ether derivative.The salt effect was discussed on the basis of the spectral data.