27356-33-8

Usage

Appearance

White to off-white solid.

Primary use

Intermediate in the production of other organic compounds.

Chemical structure

Benzene ring with a methoxy group and an acetyl group attached.

Classification

Ketone.

Fragrance

Sweet, floral scent.

Application in perfumes

Used as a fragrance ingredient in perfumes and other personal care products.

Pharmaceutical synthesis

Used in the synthesis of pharmaceuticals.

Dyes and pigments

Acts as a precursor in the production of various dyes and pigments.

InChI:InChI=1/C15H14O2/c1-17-15-10-6-5-9-13(15)11-14(16)12-7-3-2-4-8-12/h2-10H,11H2,1H3

Upstream product

• 24892-80-6 2-(1-phenylvinyl)anisole 
• 33921-62-9 2-Methoxy-phenylmagnesium-jodid 
• 84840-80-2 (p-methoxyphenyl)phenacyllead diacetate 
• 84840-85-7 (p-methoxyphenyl)-α-methylphenacyllead diacetate 
• 93-58-3 benzoic acid methyl ester 
• 578-58-5 2-methylmethoxybenzene 
• 93-25-4 2-methoxyphenylacetic acid 
• 1188264-46-1 N-methoxy-2-(2-methoxyphenyl)-N-methylacetamide 
• 100-58-3 phenylmagnesium bromide 
• 20383-28-2 N,N-diisopropyl benzamide 
• 7035-03-2 2-methoxy-benzeneacetonitrile 
• 34082-43-4 2-methoxybenzil 
• 55913-05-8 2-hydroxy-1-(2-methoxyphenyl)-2-phenylethan-1-one 
• 854630-15-2 2-(2-methoxyphenyl)-3-oxo-3-phenylpropanal 

Downstream Products

• 1839-72-1 2-phenylbenzofuran 
• 10604-22-5 3-phenylcinnoline 
• 34082-43-4 2-methoxybenzil 
• 37883-67-3 5-(2-methoxyphenyl)-4-phenylpyrimidin-2-amine 
• 1309875-54-4 4-(2-methoxy-phenyl)-3-phenyl-cyclohex-2-enone oxime 
• 1309875-55-5 5-(2-methoxy-phenyl)-4-phenyl-1,5,6,7-tetrahydro-azepin-2-one 
• 1309875-53-3 4-(2-methoxy-phenyl)-3-phenyl-cyclohex-2-enone 
• 119824-87-2 1,3-diphenyl-4-orthomethoxyphenyl pyrazoline 

Relevant academic research and scientific papers

Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+System

Chemoselective deprotonative functionalization of benzylic C-H bonds is challenging, because the arene ring contains multiple aromatic C(sp2)-H bonds, which can be competitively deprotonated and lead to selectivity issues. Recently it was found that bimetallic [MN(SiMe3)2 M = Li, Na]/Cs+ combinations exhibit excellent benzylic selectivity. Herein, is reported the first deprotonative addition of toluenes to Weinreb amides mediated by LiN(SiMe3)2/CsF for the synthesis of a diverse array of 2-arylacetophenones. Surprisingly, simple methyl benzoates also react with toluenes under similar conditions to form 2-arylacetophenones without double addition to give tertiary alcohol products. This finding greatly increases the practicality and impact of this chemistry. Some challenging substrates with respect to benzylic deprotonations, such as fluoro and methoxy substituted toluenes, are selectively transformed to 2-aryl acetophenones. The value of benzylic deprotonation of 3-fluorotoluene is demonstrated by the synthesis of a key intermediate in the preparation of Polmacoxib.

Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds

Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.

Electrochemical α-Arylation of Ketones via Anodic Oxidation of in Situ Generated Silyl Enol Ethers

An electrochemical procedure for the α-arylation of ketones has been developed. The method is based on the generation and one-pot anodic oxidation of silyl enol ethers in the presence of the arene. This strategy avoids isolation of the silyl enol intermediate and the utilization of external supporting electrolytes. Intermolecular arylations, which had not been reported so far, are possible when electron-rich arenes are utilized as coupling partners. The method has been demonstrated for a wide variety of aryl ketones and activated arenes, with moderate to good yields (up to 69%) obtained. Mechanistic insights and a theoretical rationale that explains the ketone α-arylation versus dimerization selectivity are also presented.

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.].

The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters

Commercially available cinchona alkaloids that can catalyze the enantiodivergent fluorination of β-ketodiarylphosphine oxides were developed to construct carbon-fluorine quaternary stereocenters. This protocol features a wide scope of substrates and excellent enantioselectivities, and it is scalable.

N-heterocyclic carbene-palladium-imine complex catalyzed α-arylation of ketones with aryl and heteroaryl chlorides under air atmosphere

A new structure of saturated ring skeleton monoligated NHC-Pd-Imine complex was easily synthesized and unambiguously confirmed by X-ray single crystal diffraction. It was found to be an efficient and air-stable catalyst for the α-arylation of ketones. The reaction could be operated in air without any negative effect. Non-activated aryl and heteroaryl chlorides have been successfully applied in the reaction with only 0.5 mol% catalyst loadings under air atmosphere. Excellent to good product yields were afforded.

Palladate Precatalysts for the Formation of C-N and C-C Bonds

A series of imidazolium-based palladate precatalysts has been synthesized and the catalytic activity of these air- and moisture-stable complexes evaluated as a function of the nature of the imidazolium counterion. These precatalysts can be converted under

Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles

An efficient one-pot two-step procedure for the synthesis of unsymmetrical (hetero)aryl 1,2-diketones has been developed. The reaction proceeds through a palladium-catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper-catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant. This represents the first example of the direct synthesis of unsymmetrical diaryl 1,2-diketones from arylacetonitriles. This method utilizes inexpensive, stable, nontoxic, and readily available starting materials, is highly effective in the presence of both electron-rich and electron-poor nitriles and aryltrifluoroborates, and tolerates a wide variety of functional groups. The synthetic utility of this transformation was shown by increasing the scale of the reaction and by carrying out the one-pot protocol for the preparation of quinoxaline and benzimidazole derivatives. A plausible reaction mechanism has also been proposed.

Selective Metal-Free Deoxygenation of Unsymmetrical 1,2-Dicarbonyl Compounds by Chlorotrimethylsilane and Sodium Iodide

For the first time, the combination of chlorotrimethylsilane with NaI is used as a selective reducting system toward 1,2-diketones. This combination is successfully evaluated with several unsymmetrically benzil derivatives, which are reduced in good yield

An efficient approach to construct 2-arylbenzo[b]furans from 2-methoxychalcone epoxides

An efficient and practical method for construction of 2-arylbenzo[b]furans from 2-methoxychalcone epoxides has been reported. Catalyzed by 2 mol % of BF3·Et2O, 2-methoxychalcone epoxides went through the Meerwein rearrangement, followed by deformylation in one-pot to successfully afforded 2-methoxydeoxybenzoins. Afterward, 2-arylbenzo[b]furans were obtained in high yields (87%-100%) via intermolecular cyclodehydration of 2-methoxydeoxybenzoins with 48% HBr. By utilization of this approach, the natural product stemofuran A and the key intermediate of eupomatenoid 6 have been synthesized conveniently.