25855-99-6

Usage

InChI:InChI=1/C16H14O2/c1-12-7-9-14(10-8-12)16(18)11-15(17)13-5-3-2-4-6-13/h2-10H,11H2,1H3

Upstream product

• 64-19-7 acetic acid 
• 10325-65-2 2,3-Dibromo-3-phenyl-1-p-tolyl-propan-1-one 
• 10347-11-2 4-(methylbenzoyl)imidazoline 
• 27729-96-0 trans-3-(p-tolyl)-2-benzoyloxirane 
• 97684-12-3 2-(2-Phenyl-1,3-dithian-2-yl)-4'-methylacetophenon 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 98-86-2 acetophenone 
• 127636-42-4 3-anilino-1-p-tolyl-3-phenyl-2-propen-1-one 
• 52939-90-9 (Z)-3-amino-1-phenyl-3-(4-methylphenyl)-prop-2-en-1-one 
• 4224-87-7 4-methyl-chalcone 
• 14271-73-9 4-methylbenzoyl cyanide 
• 70-11-1 α-bromoacetophenone 
• 874-60-2 4-methyl-benzoyl chloride 
• 122-00-9 para-methylacetophenone 

Downstream Products

• 29329-38-2 5-phenyl-3-(p-tolyl)isoxazole 
• 38468-92-7 2-hydroxy-4-phenyl-6-p-tolyl-nicotinonitrile 
• 65429-74-5 2-hydroxy-6-phenyl-4-p-tolyl-nicotinonitrile 
• 16112-19-9 5-(p-methylphenyl)-3-phenyl-2-isoxazole 
• 57736-14-8 2-(4'-methylphenyl)-3-benzoyl-4-phenyl-1-oxa-4-azabutadiene 
• 63914-58-9 1-(4-methylphenyl)-2-methyl-3-phenylpropan-1,3-dione 
• 143969-10-2 4-phenyl-6-(p-tolyl)-1,2-dihydropyridin-2-ol 
• 548487-51-0 6-phenyl-4-p-tolyl-pyridin-2-ol 
• 1045345-85-4 2-[-1-(4-methoxylphenyl)-3-phenyl-2-propynyl]-1-(4-methylphenyl)-3-phenyl-1,3-propanedione 
• 2431-00-7 p-methylbenzil 
• 99-94-5 p-Toluic acid 
• 65-85-0 benzoic acid 
• 6277-67-4 4-nitro-1,3-diphenyl-butan-1-one 
• 54458-30-9 2-bromo-1-(4-methylphenyl)-3-phenyl-1,3-propanedione 

Relevant academic research and scientific papers

Ag-Catalyzed Insertion of Alkynyl Carbenes into C-C Bonds of β-Ketocarbonyls: A Formal C(sp2) Insertion

Here we report a silver-catalyzed alkynyl carbene insertion into β-ketocarbonyls using alkynyl N-nosylhydrazones as alkynyl carbene precursors, which provides access to trisubstituted allenyl ketones. This reaction represents the first example of an alkynyl carbene insertion into a C-C σ bond, affording products homologated with an sp2 carbon center. The products are useful substrates for further transformations. Experimental investigations and theoretical calculations suggest the reaction proceeds through a stepwise enol cyclopropanation/retro-aldol pathway.

Rhodium-Catalyzed Aerobic Decomposition of 1,3-Diaryl-2-diazo-1,3-diketones: Mechanistic Investigation and Application to the Synthesis of Benzils

The conversion of 1,3-diaryl-2-diazo-1,3-diketones to 1,2-daryl-1,2-diketones (benzils) is reported based on a rhodium(II)-catalyzed aerobic decomposition process. The reaction occurs at ambient temperatures and can be catalyzed by a few dirhodium carboxylates (5 mol %) under a balloon pressure of oxygen. Moreover, an oxygen atom from the O2 reagent is shown to be incorporated into the product, and this is accompanied by the extrusion of a carbonyl unit from the starting materials. Mechanistically, it is proposed that the decomposition may proceed via the interaction of a ketene intermediate resulting from a Wolff rearrangement of the carbenoid, with a rhodium peroxide or peroxy radical species generated upon the activation of molecular oxygen. The proposed mechanism has been supported by the results from a set of controlled experiments. By using this newly developed strategy, a large array of benzil derivatives as well as 9,10-phenanthrenequinone were synthesized from the corresponding diazo substrates in varying yields. On the other hand, the method did not allow the generation of benzocyclobutene-1,2-dione from 2-diazo-1,3-indandione because of the difficulty of inducing the initial rearrangement.

Discovery of pyrazole N-aryl sulfonate: A novel and highly potent cyclooxygenase-2 (COX-2) selective inhibitors

Based on a new pyrazole sulfonate synthetic method, a novel class of molecules with a basic structure of pyrazole N-aryl sulfonate have been designed and synthesized. The interest in conducting intensive research stems from quite evident anti-inflammatory effects exhibited by the compounds in preliminary animal experiments. A series of compounds were synthesized by different substitutions of the R1, R2, and R3 groups. Within the series, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and phenyl 5-methyl-3-(4-(trifluoromethyl) phenyl)-1H-pyrazole-1-sulfonate exhibited excellent anti-inflammatory activity (% inhibition of auricular edemas = 27.0 and 35.9, respectively); the in vivo analgesic activity of phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate was confirmed to be effective (inhibition ratio of writhing = 50.7% and 48.5% separately), and compounds phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate were identified as selective COX-2 inhibitors (SI = 455, 10,497 and >189 severally). In Acute Oral Toxicity assays conducted in vivo, the lethal dose 50 (LD50) of 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate to mice was >2000 mg/kg BW.

Method for synthesizing 1, 3-dicarbonyl compound based on terminal alkyne and acyl halide by one-pot process

The invention belongs to the technical field of catalytic synthesis, and discloses a method for synthesizing a 1, 3-dicarbonyl compound by a one-pot process, and the method comprises the following steps: by using simple palladium and copper salts as catalysts, reacting terminal alkyne with acyl halide at 0-80 DEG C for 0.5-12 hours under the action of trifluoromethanesulfonic acid to obtain the 1,3-dicarbonyl compound, wherein the molar ratio of the terminal alkyne to the acyl halide to the palladium salt to the copper salt to the trifluoromethanesulfonic acid is 1 to (1 to 2) to (0.00001 to0.10) to (0.00001 to 0.10) to (0.00004 to 0.40); the catalysts used in the method are common the commercialized palladium salt and copper salt, reagents used in the reaction are commercialized reagents, in addition, the raw materials are cheap and easy to obtain, functional group tolerance is good, reaction conditions are mild, operation is easy and convenient, and atom economy is high.

Synthesis and Characterization of Pheox– and Phebox–Aluminum Complexes: Application as Tunable Lewis Acid Catalysts in Organic Reactions

Pheox– and Phebox–aluminum complexes were synthesized and subsequently characterized by spectroscopic analysis. These complexes acted as Lewis acid catalysts, and their catalytic activities were controlled by using the Pheox, Phebox, and heteroatom ligands. The Pheox–aluminum complex exhibited an opposite substrate selectivity to AlCl3 in a competitive hetero-Diels–Alder reaction between electron-rich and electron-deficient aldehydes.

An efficient tandem synthesis of chromones from: O -bromoaryl ynones and benzaldehyde oxime

An effective transition-metal-free strategy was developed for the preparation of chromones from o-bromoaryl ynones and benzaldehyde oxime through sequential C-O bond formation. This cyclization reaction could well tolerate a wide range of functional groups, and the corresponding chromones were given in moderate to excellent yields. Mechanistically, benzaldehyde oxime as a hydroxide source and 1,3-diketone derivatives as reaction intermediates were involved in this transformation.

Novel Bifunctionalization of Activated Methylene: Base-Promoted Trifluoromethylthiolation of β-Diketones with Trifluoromethanesulfinyl Chloride

A novel bifunctionalization of activated methylene was achieved successfully through the base-promoted trifluoromethylthiolation of β-diketones or β-ketoesters with trifluoromethanesulfinyl chloride. A series of α-trifluoromethylthiolated α-chloro-β-diketones and α-chloro-β-ketoesters were obtained in moderate to good yields under mild conditions. When β-diketones containing a phenyl group with a hydroxyl or amino substituent at the ortho position were used as substrates, intramolecular trifluoromethylthiolation/cyclization reaction took place to give the corresponding cyclic products. Furthermore, the protocol could be extended to perfluoroalkylthiolation with the sodium perfluoroalkanesulfinate/POCl3 system. On the basis of experimental results, plausible mechanisms are proposed.

Method of preparing 1,3-diketone compound by acetyenic ketone

The invention relates to a preparation method of preparing a 1,3-diketone compound by acetyenic ketone. The preparation method comprises the following steps: S1, putting alpha-alkynyl ketone compound,water, gold salt and silver salt in a reaction solvent to obtain a precursor mixture, wherein the molar ratio of the alpha-alkynyl ketone compound, water, gold salt and silver salt is 1: (1-50): (0.001-0.10): (0.002-0.15); and S2, putting the precursor mixture obtained in the S1 to react at a reaction temperature of 0-50 DEG C to obtain the 1,3-diketone compound, wherein the reaction time is 5 min to 48 h. The method is simple in reaction condition, free of acid or alkaline additives and high in yield, and can be applied to modern production on a large scale.

An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources

An effective phosphine-catalyzed protocol has been established for the syntheses of 1,3-diketones and nitriles from alkynones with oximes as hydroxide surrogates. This method features the use of a phosphine catalyst, compatibility with various functional groups and ambient temperature, which makes this approach very practical. A plausible mechanism was proposed.

Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof

The invention discloses a pyrazole compound containing N-aryl sulfonate. A structural formula of the pyrazole compound is shown in the description. Proofed by pharmacological study, the pyrazole compound has the advantages that the activity of cyclooxygenase 2 is inhibited; the high-efficiency inhibition function on the generation of cyclooxygenase 2 due to inflammation mediums is realized, so that the pyrazole compound can be used as an active matter, and the prepared anti-inflammation medicine can be used for treating the inflammations, such as rheumatic arthritis and rheumatalgia, and the diseases and symptoms, such as fevers.