3141-93-3

Usage

Uses

Used in Organic Synthesis:
3',4'-DIMETHOXY-2-PHENYLACETOPHENONE is used as a building block in organic synthesis for the creation of various compounds and drugs, leveraging its unique structure and reactivity.
Used in Pharmaceutical Research:
In pharmaceutical research, 3',4'-DIMETHOXY-2-PHENYLACETOPHENONE is utilized as a key intermediate in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Analytical Chemistry:
3',4'-DIMETHOXY-2-PHENYLACETOPHENONE serves as a reagent in analytical chemistry, where its properties are employed for the detection, measurement, or analysis of other substances.
Used in Perfume and Fragrance Production:
This chemical compound is used as a component in the production of perfumes and fragrances, capitalizing on its aromatic characteristics to enhance the sensory experience of these products.
Used in Antioxidant and Anti-Inflammatory Applications:
3',4'-DIMETHOXY-2-PHENYLACETOPHENONE is studied for its potential antioxidant and anti-inflammatory properties, indicating its possible use in health and wellness products or treatments.

InChI:InChI=1/C16H16O3/c1-18-15-9-8-13(11-16(15)19-2)14(17)10-12-6-4-3-5-7-12/h3-9,11H,10H2,1-2H3

Upstream product

• 103-82-2 phenylacetic acid 
• 91-16-7 1,2-dimethoxybenzene 
• 1521-41-1 veratramide 
• 6921-34-2 benzylmagnesium chloride 
• 72867-66-4 N-[1-Cyano-1-(3,4-dimethoxy-phenyl)-2-phenyl-ethyl]-N-phenyl-benzamide 
• 37672-97-2 2-(N_.N-dimethylamino)-2-(3,4-dimethoxyphenyl)acetonitrile 
• 100-44-7 benzyl chloride 
• 37673-01-1 2-(N,N-diethylamino)-2-(3,4-dimethoxyphenyl)acetonitrile 
• 103-80-0 phenylacetyl chloride 
• 108-86-1 bromobenzene 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 54840-97-0 2-(3, 4-dimethoxyphenyl)-2-(phenylamino)acetonitrile 
• 100-39-0 benzyl bromide 

Downstream Products

• 50882-54-7 (3,4-dimethoxy-bibenzyl-α-yl)-methyl-amine 
• 101293-65-6 3,4-dimethoxy-deoxybenzoin oxime 
• 66659-96-9 2-bromo-1-(3,4-dimethoxyphenyl)-2-phenylethanone 
• 132180-47-3 3,4-dimethoxy-deoxybenzoin semicarbazone 
• 109867-22-3 3,4-dimethoxy-deoxybenzoin-phenylhydrazone 
• 80235-73-0 N-<1-(3,4-dimethoxyphenyl)-2-phenylethyl>formamide 
• 29277-22-3 1-(3,4-dimethoxy-phenyl)-3-morpholin-4-yl-2-phenyl-propan-1-one 
• 69511-77-9 1-(4,5-dimethoxy-2-nitrophenyl)-2-phenyl-1-ethanone 
• 3892-93-1 1-(3,4-dimethoxyphenyl)-2-phenylethane 
• 3864-15-1 1-(3,4-Dimethoxyphenyl)-2-phenylethanol 
• 79997-18-5 1-(3,4-dimethoxyphenyl)-2-phenylethane-1,2-dione 
• 106053-33-2 2,2-Dideutero-1-(3,4-dimethoxyphenyl)-2-phenylethanon 
• 106053-35-4 1-(3,4-Dimethoxyphenyl)-1-deutero-2-phenylethanol 
• 102520-52-5 1-(3,4-Dimethoxy-phenyl)-2-phenyl-butan-1-one 

Relevant academic research and scientific papers

Palladium-catalyzed denitrative α-arylation of ketones with nitroarenes

The palladium-catalyzed α-arylation of ketones with readily available nitroarenes and nitroheteroarenes provides access to useful α-aryl and α-heteroaryl ketones. The use of the Pd/ BrettPhos catalysts was critical to achieve high efficiency for these transformations, whereas other catalysts led to decreased yields or no conversions. The intramolecular type substrate was also applied in this methodology and gave a chromone derivative. Polyaromatic carbonyl compounds can be easily obtained by multicomponent tandem reactions, via nucleophilic aromatic substitution (SNAr) or cross-coupling reaction followed by this denitrative arylation. Kinetic experiments show that the electronic effect of nitrobenzenes has a greater effect on the reaction rate than the electronic effect of ketones.

Regioselection in the synthesis of 4-benzyltetral-1-ones and the new 4-arylbenzosuber-1-ones

The intramolecular Friedel-Crafts acylation of 4,5-diarylpentanoic acids has the possibility to cyclise to either a 6-membered ring to give 4-benzyltetral-1-one or a 7-membered ring to give 4-arylbenzosuber-1-one. Of these, only the former compound class has previously been reported. The impact of the substituents positioning on the outcome of the cyclisation has been investigated. The complete formation of either the tetralone or the benzosuberone regioisomer was possible under the same reaction conditions, dependent upon the ring activation and/or deactivation of the chosen substituents. Selected bromo or methoxy substituents could be used as auxiliaries, included in precursors to afford the desired regioisomer and then subsequently removed.

Benzylic aroylation of toluenes with unactivated tertiary benzamides promoted by directed ortho-lithiation

The deprotonative functionalization of toluenes, for their weak acidity, generally needs strong bases, thus leading to the requirement of harsh conditions and the generation of by-products. Direct nucleophilic acyl substitution reaction of amides with organometallic reagents could provide an ideal solution for ketone synthesis. However, the inert amides and highly reactive organometallic reagents bring great challenges for an efficient and selective synthetic approach. Herein, we reported an lithium diisopropylamide (LDA)-promoted benzylic aroylation of toluenes with unactivated tertiary benzamides, providing a direct and efficient synthesis of various aryl benzyl ketones. This process features a kinetic deprotonative functionalization of toluenes with a readily available base LDA. Mechanism studies revealed that the directed ortho-lithiation of the tertiary benzamide with LDA promoted the benzylic kinetic deprotonation of toluene and triggered the nucleophilic acyl substitution reaction with the amide. [Figure not available: see fulltext.].

Metal-free synthesis of ketones by visible-light induced aerobic oxidative radical addition of aryl hydrazines to alkenes

A green and cost-effective method has been developed for the conversion of alkenes to ketones under metal-free conditions. The reaction involves the oxidative addition of alkenes with aryl radicals, which are generated by visible-light induced aerobic oxidation of arylhydrazines. The key features of this reaction include broad substrate scope, readily available reagents and amenability to gram-scale synthesis.

Rh(III)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines

A Rh(iii)-catalyzed C-H activation/cyclization of oximes and alkenes for facile and regioselective access to isoquinolines has been developed. This protocol features mild reaction conditions and easily accessible starting materials, and has been applied to the concise synthesis of moxaverine. A kinetic isotope effect study was conducted and a plausible mechanism was proposed.

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 substituted phenanthrofurans

A three-step protocol toward phenanthrofurans 1 starting with deoxybenzoins 3 is developed with moderate to good yield. A facile process is carried out for the (1) α-propargylation of 3 with NaH and propargyl bromide 2 in refluxing THF, (2) Bi(OTf)3-mediated cycloisomerization of γ-ynones 4 with 4 ? molecular sieves in MeNO2 at rt, and (3) photolytic Scholl annulation of 2,3-diarylfurans 5 with I2 in EtOAc at rt. The key structures of 1 are confirmed by X-ray crystallographic analysis.

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.

Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction

A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus.

Synthesis of new 1,2-Diphenyl-4, 5-dihydro-3H-3-benzazepines

1,2-Diphenyl-4,5-dihydro-3H-3-benzazepine derivatives (2a-d) were synthesized via cyclization reaction of N-[2-(2-iodophenyl)ethyl]-α-phenylphenacylamines (5a-c) and (5e) with n-C4H9Li, followed by dehydration of the cyclization prod