5543-97-5

Usage

Chemical Properties

White Powder

Uses

Intermediate in the preparation of clomiphene and tamoxifen analogs.

InChI:InChI=1/C21H18O2/c1-23-19-14-12-17(13-15-19)20(16-8-4-2-5-9-16)21(22)18-10-6-3-7-11-18/h2-15,20H,1H3

Upstream product

• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 100-66-3 methoxybenzene 
• 7664-93-9 sulfuric acid 
• 5543-96-4 1-(4-methoxy-phenyl)-1,2-diphenyl-ethane-1,2-diol 
• 611-94-9 4-Methoxybenzophenone 
• 100-47-0 benzonitrile 
• 4237-52-9 2-(4-methoxyphenyl)-1,1-diphenylethane-1,2-diol 
• 451-40-1 phenyl benzyl ketone 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 623-12-1 4-chloromethoxybenzene 
• 7153-12-0 dimethyl (2-oxo-1,2-diphenylethyl) phosphate 
• 19820-47-4 4-methoxyphenyl 2,2-dimethylpropionate 
• 367935-16-8 2-hydroxy-2-(4-methoxyphenyl)-1,2-diphenylethanone 
• 100-17-4 para-methoxynitrobenzene 

Downstream Products

• 153777-86-7 (trans)-1-chloro-2-(4-β-chloroethoxyphenyl)-1,2-diphenylethene 
• 153777-92-5 (R,S)-1-(4-benzyloxyphenyl)-1,2-diphenyl-butan-2-ol 
• 151835-01-7 2-(4-benzyloxyphenyl)-1,2-diphenyl-ethan-1-one 
• 153777-85-6 2-(4-β-chloroethoxyphenyl)-1,2-diphenyl-ethan-1-one 
• 97818-83-2 chloro-tam 
• 69967-79-9 ICI 77949 
• 5543-98-6 2-(4-hydroxyphenyl)-1,2-diphenyl-ethan-1-one 
• 57272-39-6 2-Hydroperoxy-2-(4-methoxy-phenyl)-1,2-diphenyl-ethanone 
• 834-14-0 p-benzylanizole 
• 65-85-0 benzoic acid 

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.

Method for preparing alpha-aryl ketone compound by using palladium complex

The invention relates to a method for preparing an alpha-aryl ketone compound by using a palladium complex, which comprises the steps of in the presence of alkali, taking ketone and halogenated hydrocarbon as raw materials, taking the palladium complex containing an ortho-carborane benzothiazole structure as a catalyst, and carrying out alpha-halogenation reaction at room temperature to prepare the alpha-aryl ketone compound. Compared with the prior art, the palladium complex containing the ortho-carborane benzothiazole structure is applied to catalysis of the alpha-halogenation reaction of ketone and halogenated hydrocarbon, the alpha-aryl substituted ketone compound is prepared through a one-pot method, synthesis of the alpha-aryl ketone compound at room temperature by using simple, easily available and cheap raw materials is achieved, and the method has the advantages of low catalyst use equivalent, mild reaction conditions, more catalytic substrates, high substrate universality and high yield.

Metal Free, Direct and Selective Deoxygenation of α-Hydroxy Carbonyl Compounds: Access to α,α-Diaryl Carbonyl Compounds

An efficient, metal free, direct and selective deoxygenation of α-hydroxy carbonyl compounds is achieved with the aid of catalytic amount of aqueous HClO4 (70 %) and triethylsilane as hydride source. A variety of α-hydroxy-α,α-diaryl carbonyl compounds are selectively deoxygenated to give α,α-diaryl carbonyl compounds in good to excellent yields. Intermediacy of α-keto carbenium ion is proposed on the basis of some control experiments and atmospheric pressure chemical ionization mass spectral analysis.

Aqueous α-Arylation of Mono- and Diarylethanone Enolates at Low Catalyst Loading

Acetophenone and deoxybenzoin derivatives are selectively α-arylated using a combination of very small amounts of palladium acetate and diphenylphosphine oxide as catalyst system and water as the only solvent. Target di- and triarylethanones are isolated virtually free of metal residues, and the reaction is amenable to gram-scale. A mechanistic proposal based on TEM images, poisoning experiments, kinetic plot and ESI-MS spectrometry is also provided. (Figure presented.).

α,α-Diarylethylene Glycols as Valuable Precursor for Synthesis of 1,1-Diarylethenes and α,α-Diaryl Acetaldehydes

Towards assembling of diarylmethine unit present in biologically important molecules, we have developed a new Weinreb Amide (WA) based building block derived from glycolic acid. The WA functionality present in this building block permits the sequential addition of various arylmagnesium bromide reagents in a controlled manner that enables assembly of a diarylmethine unit. The developed synthetic route provides easy access to important diarylethenes and α,α-diarylethylene glycols. The synthesized α,α-diarylethylene glycols provide access to synthetically important symmetrical and unsymmetrical α,α-diaryl acetaldehydes as valuable intermediates.

LIGAND, NICKEL COMPLEX COMPRISING LIGAND, AND REACTION USING NICKEL COMPLEX

PROBLEM TO BE SOLVED: To provide a method for directly carrying out arylation, especially α-arylation, of a carbonyl compound or a thiocarbonyl compound by using a more inexpensive phenol derivative and a nickel catalyst, and to provide a novel nickel cat

Nickel-catalyzed α-arylation of ketones with phenol derivatives

The nickel-catalyzed α-arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful α-arylketones. For this transformation, 3,4-bis(dicyclohexylphosphino) thiophene (dcypt) was identified as a new, enabling, air-stable ligand for this transformation. The intermediate of an assumed C-O oxidative addition was isolated and characterized by X-ray crystal-structure analysis. The nickel-catalyzed α-arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful α-arylketones. The use of 3,4-bis(dicyclohexylphosphino)thiophene (dcypt) as an air-stable ligand enables this transformation. The intermediate of an assumed C-O oxidative addition was isolated and characterized by X-ray crystal-structure analysis.

Weinreb amide based building blocks for convenient access to 1,1-diarylethenes and isocombretastatin analogues

A successful strategy based on the synthetic equivalent containing Weinreb amide functionality for the convenient access to 1,1-diarylethenes in general and for the isocombretastatin analogues in particular has been developed from the commercially available glyoxalic acid. The convenience with which the structural variations can be made in assembling the aryl residues shows generality associated with the developed strategy. The intermediates also provide access to 1,2,2-triarylethanones, represented by the synthesis of advanced intermediate of tamoxifen.

Lewis acid-promoted friedel-crafts alkylation reactions with α-ketophosphate electrophiles

The BF3·OEt2-promoted nucleophilic substitution of α-aryl-α-ketophosphates to afford α,α-diaryl ketone products is described. Electron-rich α-ketophosphates perform best, with electron-neutral and electron-poor substrates also tolerated. The reaction is tolerant of a range of aromatic, heteroaromatic, and nonaromatic nucleophiles, with yields ranging from 44% to 84%. Enantioenriched starting material yields racemic product, suggesting an SN1 pathway via an acylcarbenium ion.

PCP-Bis(phosphinite) pincer complexes: new homogeneous catalysts for α-arylation of ketones

Two new p-alkoxycarbonylated palladium bis(phosphinite) PCP pincer complexes are easily prepared and for the first time evaluated as homogeneous catalysts in α-arylation of ketone enolates. Apart from the total absence of phenyl-aryl exchange by-products and significantly low catalyst loadings, the general α-arylation protocols described in this letter feature not only a broad applicability to a range of ketones and aryl bromides with marked electronic and steric differences but also the possibility to generate mono-diarylated products.