2491-32-9

Usage

Chemical Properties

Cream crystalline powder

Preparation

– Obtained by reaction of phenylacetic acid with phenol, ? in the presence of zinc chloride (Nencki reaction), ? in the presence of zinc chloride and phosphorous oxychloride for 24 h at r.t. (75%) ; ? in the presence of polyphosphoric acid in a boiling water bath for 15 min (28%) or at 100° (19%) ; ? in the presence of boron trifluoride at 80° for 2 h (87%) ; ? in the presence of boron trifluoride etherate under argon on a water bath for 1.5 h (75%).

InChI:InChI=1/C14H12O2/c15-13-8-6-12(7-9-13)14(16)10-11-4-2-1-3-5-11/h1-9,15H,10H2

Upstream product

• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 722-01-0 phenyl phenylacetate 
• 103-80-0 phenylacetyl chloride 
• 108-95-2 phenol 
• 103-82-2 phenylacetic acid 
• 2491-31-8 2-hydroxy-deoxybenzoin 
• 7446-70-0 aluminium trichloride 
• 540-38-5 p-Iodophenol 
• 100-44-7 benzyl chloride 
• 62673-31-8 benzyl(bromo)zinc 
• 13939-06-5 molybdenum hexacarbonyl 
• 106-41-2 4-bromo-phenol 
• 54125-02-9 danishefsky's diene 
• 31739-46-5 1-phenylbut-3-yn-2-one 

Downstream Products

• 63187-05-3 1-(4-hydroxy-phenyl)-2,3-diphenyl-3-piperidino-propan-1-one 
• 32599-27-2 1-(4-hydroxy-phenyl)-2-phenyl-3-piperidin-1-yl-propan-1-one 
• 102156-36-5 4-hydroxy-3-piperidinomethyl-deoxybenzoin 
• 63192-19-8 1-(4-butoxyphenyl)-2-phenylethanone 
• 38495-73-7 1-(4-ethoxyphenyl)-2-phenylethanone 
• 69342-32-1 1-(4-isopropoxyphenyl)-2-phenylethanone 
• 857562-76-6 4-(2-butoxy-ethoxy)-deoxybenzoin 
• 79838-57-6 2-phenyl(4-diethylaminoethoxyphenyl)ethan-1-one 
• 6335-83-7 4-(2-phenylethyl)phenol 
• 855242-75-0 2,3-bis-(4-hydroxy-phenyl)-1,4-diphenyl-butane-2,3-diol 
• 34544-90-6 4,α-diacetoxy-stilbene 
• 14293-14-2 4-(benzyloxy)phenyl benzyl ketone 
• 61078-33-9 1-(4-hydroxy-phenyl)-3-(4-methoxy-phenyl)-2-phenyl-propenone 
• 110050-16-3 4-(3-diethylamino-propoxy)-deoxybenzoin 

Relevant academic research and scientific papers

Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts

A ligand and base-free copper catalyzed synthetic method for the efficient α-arylation of aromatic ketones is described. In order to avoid strong bases, ketone-derived silyl enol ethers were employed. Their reaction with diaryliodonium salts as aryl source provided the intermolecular C–C coupling displaying good functional group tolerance and requiring low catalyst loading.

Mn/Cu catalyzed addition of arylboronic acid to nitriles: Direct synthesis of arylketones

A direct and efficient synthesis of arylketones via arylboronic acid addition to nitriles in presence of inexpensive Mn/Cu catalytic system is reported. The use of non-precious Mn and Cu salts has been found to be highly advantageous both in terms of accessibility as well as cost effectiveness. A series of arylboronic acids as well as nitriles were used to synthesize a variety of symmetrical and unsymmetrical arylketones. Based on the literature studies, the reaction mechanism is anticipated to go through an aryl radical intermediate which reacted with the copper activated nitrile to give the desired arylketones after the hydrolysis of the imine intermediate.

PtO2/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups

A highly efficient PtO2/PTSA catalyst system for the hydration of a wide array of alkynes was developed. This method proved to be compatible with a large range of functional groups and the ketone products were obtained in high yields. The scope of this methodology was also extended to the synthesis of 3-Aryl-isochromenones,-indoles and-benzofurans.

A general synthesis of ynones from aldehydes via oxidative C-C bond cleavage under aerobic conditions

We describe a direct synthesis of various ynones from readily available aldehydes and hypervalent alkynyl iodides. In this method, a gold catalyst and a secondary amine work synergistically to produce the trisubstituted allenyl aldehyde, which can be conv

Diarylated ethanones from Mo(CO)6-mediated and microwave-assisted palladium-catalysed carbonylative Negishi cross-couplings

Two protocols for palladium-catalysed carbonylative Negishi cross-couplings were developed for aryl iodides and aryl bromides. The two main breakthroughs were that molybdenum hexacarbonyl [Mo(CO)6] could be used as a solid in situ source of CO, and that controlled microwave irraditaion could be used for heating. Consequently, the reactions were safe (in contrast to when CO gas was used) and fast (in comparison to when conventional heating was used). The carbonylative cross-coupling reactions were carried out using commercially available benzylzinc bromide in closed vials (90-120°C for 0.5-1 h) to give a set of diarylated ethanones, a common pharmacophore found in several pharmaceuticals, in moderate to high isolated yields (47-84 %). The mild three-component carbonylation protocol presented here is operationally simple, safe, and rapid, and the formation of the carbonylative Negishi cross-coupling product is favoured over the product of Negishi cross-coupling. Copyright

Design, synthesis, and cytotoxic activities of new 2,4,5-triarylimidazoles

A new group of 2,4,5-triarylimidazoles containing N,N-dimethylaminoethoxy or piperidinyl ethoxy group at the para position of the C-5 phenyl ring were synthesized and their cytotoxic activities were evaluated on three different breast cancer cell lines using MTT assay. The compounds contain various substituents at the para position of C-2 phenyl ring. Among the synthesized compounds, 4-(5-(4-(2-piperidin-1-yl)ethoxy)phenyl)-4-phenyl-1H-imidazol-2-yl) phenol (11e) and 1-2-(4-(2,4-diphenyl-1H-imidazol-5-yl)phenoxy)ethyl) piperidine (11h) with IC50s of less than 0.1 μM on all three cell lines were the most potent cytotoxic compounds.

A convenient one-pot completely stereoselective synthesis of trans-4-Hydroxystilbenes and its derivatives and X-ray structure of its precursor

The synthesis of E-isomer of 4-Hydroxystilbene and its derivatives 3 by reductive elimination of the carbonyl function in 2-phenyl-1-(4-hydroxyphenyl)ethan-1-one and its derivatives 2 and the X-ray structure of 2a are described.

Triphenylalkene derivatives and their use as selective estrogen receptor modulators

The invention provides novel selective estrogen receptor modulator compounds of the general formula: wherein R1 and R2, which are the same or different are a) H, halogen, OCH3, OH; or ?where X is O, NH or S; and n is an integer from 1 to 4; and R4 and R5, which are the same or different, are a 1 to 4 carbon alkyl, H, —CH2C≡CH or —CH2CH2OH; or R4 and R5 form an N-containing five- or six-membered ring or heteroaromatic ring; or c) —Y—(CH2)nCH2—O—R6 where Y is O, NH or S and n is an integer from 1 to 4; and R6 is H, —CH2CH2OH, or —CH2CH2Cl; or d) 2,3-dihydroxypropoxy, 2-methylsulfamylethoxy, 2-chloroethoxy, 1-ethyl-2-hydroxyethoxy, 2,2-diethyl-2-hydroxyethoxy or carboxymethoxy; and R3 is H, halogen, OH or —OCH3; stereoisomers thereof and their non-toxic pharmaceutically acceptable salts and esters and mixtures thereof, which compounds exhibit valuable pharmacological properties.

Photo-fries rearrangements of phenyl phenylacylates in polyethylene films. Comparison of reactivity and selectivity with 1-naphthyl phenylacylates

The fates and kinetics of recombination of singlet radical pairs generated by photolyses of three phenyl phenylacylates have been examined in unstretched and stretched polyethylene films. Comparisons with results from photolyses of analogous 1-naphthyl phenylacylates in the same media lead to the conclusions that (1) phenoxy is less reactive overall than 1-naphthoxy toward a common phenylacyl radical but (2) the constrained cages in which the radical pairs reside exert greater control over the movements of the 1-naphthoxy/phenylacyl pairs. The reasons for these observations are discussed in the context of the shapes and van der Waals volumes of the radical pairs, the void volumes of sites in native polyethylene films, and the electronic properties of the aryloxy radicals. The fates and kinetics of recombination of singlet radical pairs generated by photolyses of three phenyl phenylacylates have been examined in unstretched and stretched polyethylene films. Comparisons with results from photolyses of analogous 1-naphthyl phenylacylates in the same media lead to the conclusions that (1) phenoxy is less reactive overall than 1-naphthoxy toward a common phenylacyl radical but (2) the constrained cages in which the radical pairs reside exert greater control over the movements of the 1-naphthoxy/phenylacyl pairs. The reasons for these observations are discussed in the context of the shapes and van der Waals volumes of the radical pairs, the void volumes of sites in native polyethylene films, and the electronic properties of the aryloxy radicals.

Nickel catalysed electrosynthesis of ketones from organic halides and iron pentacarbonyl. Part 2: Unsymmetrical ketones

Unsymmetrical aryl-benzyl or aryl-alkyl ketones are obtained by electrolysing in an undivided cell a DMF solution containing two organic halides, iron pentacarbonyl and a catalytic amount of a nickel-2,2′-bipyridine complex.