4173-65-3

Usage

General Description

1-Propanone, 3-[(4-methoxyphenyl)amino]-1-phenyl- is an organic compound with the chemical formula C17H17NO2. It is a derivative of 1-propanone, more commonly known as acetone, with an amino group attached to the third carbon atom and a phenyl and methoxy group attached to the first carbon atom. 1-Propanone, 3-[(4-methoxyphenyl)amino]-1-phenyl- is also known as 4'-methoxyacetophenone and is often used in the synthesis of various pharmaceuticals and organic chemical products. It is commonly utilized as a building block in the production of dyes, perfumes, and other organic compounds due to its aromatic and functional group properties. Additionally, it is used in the production of pharmaceutical intermediates and as a raw material in the synthesis of other chemical compounds.

Upstream product

• 94-38-2 3-diethylamino-1-phenyl-propan-1-one 
• 104-94-9 4-methoxy-aniline 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 701-56-4 4-methoxy-N,N-dimethylanilne 
• 879-72-1 3-(dimethylamino)propiophenone hydrochloride 
• 50-00-0 formaldehyd 
• 4747-13-1 α-methoxystyrene 
• 5409-66-5 3-benzoyl-4-hydroxy-1-methyl-4-phenylpiperidine 
• 2298-49-9 N-methyl-3-oxo-N-(3-oxo-3-phenylpropyl)-3-phenylpropan-1-aminium chloride 
• 3506-36-3 3-dimethylaminopropiophenone 
• 768-03-6 Phenyl vinyl ketone 
• 98-86-2 acetophenone 

Downstream Products

• 46870-92-2 4-Phenyl-6-methoxyquinoline 
• 20392-68-1 3-(4'-Methoxyphenylamino)-1-phenylpropan-1-ol 
• 78993-91-6 2-Chloro-3-(4-methoxy-phenyl)-6-phenyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide 
• 872515-55-4 N-(4-methoxyphenyl)-N-(3-oxo-3-phenylpropyl)propenamide 
• 109765-68-6 (+/-)-α-4-hydroxy-3-methyl-4-phenylpiperidine 
• 76061-96-6 4-Phenyl-6-methoxy-1,2,3,4-tetrahydroquinoline 
• 76061-92-2 1-Chloroacetyl-4-phenyl-6-methoxy-1,2,3,4-tetrahydroquinoline 
• 95886-03-6 2-Aziridin-1-yl-3-(4-methoxy-phenyl)-6-phenyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide 
• 78994-12-4 2-Ethoxy-3-(p-anisyl)-6-phenyl-3,4-dihydro-1,3,2-oxazaphosphorin-2-oxide 
• 78994-09-9 Diethyl-[3-(4-methoxy-phenyl)-2-oxo-6-phenyl-3,4-dihydro-2H-2λ⁵-[1,3,2]oxazaphosphinin-2-yl]-amine 
• 89410-04-8 2-Chloro-3-(4-methoxy-phenyl)-6-phenyl-[1,3,2]oxazaphosphinane 2-oxide 
• 89410-10-6 2-Aziridin-1-yl-3-(4-methoxy-phenyl)-6-phenyl-[1,3,2]oxazaphosphinane 2-oxide 
• 1048974-48-6 1-phenyl-3-(4-methoxyphenyl)-6-phenyl-3,4-dihydropyrimidin-2(1H)-one 
• 1032606-24-8 ethyl (E)-3-[N-(4-methoxyphenyl)-N-(3-oxo-3-phenylpropyl)carbamoyl]acrylate 

Relevant academic research and scientific papers

Stereoselective Construction of γ-Lactams via Copper-Catalyzed Borylacylation

A versatile and highly stereoselective borylative cyclization to generate polyfunctionalized γ-lactams has been developed. The stereoselective synthesis of these key ring systems is crucial due to their ubiquity in natural products. We report the diastero- and enantioselective construction of di- and trisubstituted γ-lactam cores, with examples containing an enantioenriched quaternary carbon.

Silver-promoted (radio)fluorination of unsaturated carbamates via a radical process

The intramolecular fluorocyclization of unsaturated carbamates is described here using a hypervalent iodine reagent in the presence of a silver catalyst. Both (hetero)aryl-substituted olefins and acrylamides can be utilized as effective substrates. Preliminary mechanistic investigations suggest that the reaction proceeds via a cyclization/1,2-(hetero)aryl migration/fluorination cascade involving an unusual radical process. Furthermore, starting from no-carrier-added [18F]TBAF, a simple one-pot, two-step cascade method was developed for the generation of 18F-labeled heterocycles with high radiochemical purity.

Mannich bases as synthetic intermediates: Convenient synthesis of functionalized 1,2,4-triazepines, 1,4-diazepines and 1,5-diazocines

Transamination between the ketonic Mannich bases 1a, b and primary arylamines gave a series of ketonic sec-Mannich bases 2a - h. A variety of tetrahydro-1,2,4-triazepines 3a - f have been synthesized by treating the arylhydrazones of 2 with formaldehyde. A similar reaction with the benzenesulfonylhydrazone of 2b afforded 4. The 3-styryl-2H-1,2,4-triazepine 5 was obtained from the phenylhydrazone of 2a and cinnamaldehyde. Treatment of arylhydrazones of the 4-methoxystyryl keto base 7 with formaldehyde and cinnamaldehyde afforded the 3,4,5,6-tetrahydro-2H-1,2,4-triazepines 8a, b. Mannich reaction with 4-(p-hydroxyphenyl)-tetrahydro-1,2,4-triazepine 3d afforded the Mannich bases 9, 10 and 11. The reaction of 1b with o-phenylenediamine leads to the 1,5-benzodiazepine 13. The new tetrahydro- 1,4-diazepine and tetrahydro-1,5-diazocine Mannich bases 15 and 17 were obtained from 1b and ethylenediamine or 1,3-diaminopropane, respectively. The bi(piperidine) derivative 19 was obtained from 1a and 1,3-diaminopropane.

Amine exchange reactions in ionic liquid

An operationally simple, inexpensive, efficient, and environmentally friendly protocol for the amine exchange reactions of 3-N,N- dimethylaminopropiophenone and N,N-dimethylaminomethylferrocene with primary aryl amines is developed using the ionic liquid

Mannich bases as synthetic intermediates: Alkylation of amines and diamines with bis-ketonic Mannich bases

The bis-ketonic Mannich base, N,N-bis(β-benzoylethyl)methylamine hydrochloride (1) reacts with primary arylamines and diamines to give ketonic sec-arylamines 3a-e and 4. The piperidines 7a-c were obtained from 1 and primary alkylamines, whereas the 1,4-diazepine derivative 10 was obtained from 1 and ethylenediamine. Treatment of the bis-base l,4-di[β-(N-morpholino) propionyl]benzene bis(hydrochloride) (11) with primary arylamines gave the corresponding bis-(sec-arylamines) 12a - b, whereas its reaction with o-phenylenediamine afforded the bis[1,5-benzodiazepine] ring system 14. The synthesis of the diazacyclophane ring system 15 has been achieved by treating 11 with piperazine. Attempted synthesis of 4-aza-[7]-paracyclophane (16) from 11 and benzylamine led to 17. The reaction of 1 or 11 with phenylhydrazine gave the 2-pyrazolines 18 and 19. Treatment of 3 or 4 with phenylhydrazine and formaldehyde afforded the 2H-1,2,4-triazepines 20a-c and the bis[2H-1,2,4-triazepine] ring system 21.

A convenient synthesis of novel 1,3,4-triaryl-3,4-dihydropyrimidin-2(1H)- ones by cyclization of aromatic isocyanates with β-arylamino-1- phenylpropan-1-ones

(Chemical Equation Presented) A simple one-step method for preparation of novel 1,3,4-triaryl-3,4-dihydropyrimidin-2(1H)-ones has been developed by reaction of aromatic isocyanates with β-arylamino-1-phenylpropan-1-ones in refluxing toluene in the presence of KHSO4 and HCl.

Conversion of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol by arylamines and arylhydrazines. Synthesis of 3-arylamino-1-oxo-1-phenylpropanes and 1,3-diarylpyrazoles and their fragmentation under electron impact

It has been established that on heating, 3-benzoyl-4-hydroxy-1-methyl-4- phenylpiperidine is ring-opened in the presence of arylamines by a type of retroaldol reaction, with subsequent transamination of the intermediate Mannich base and the formation of 3-arylamino-1-oxo-1-phenylpropanes. When using arylhydrazines this γ-piperidol is recyclized with the formation of 1,3-diarylpyrazoles and their 4,5-dihydro derivatives. The mass spectral behavior of a series of 3-arylamino-substituted 1-phenylpropanones has been studied.

Reaction of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol with arylamines and arylhydrazines. Synthesis of 3-arylamino-1-oxo-1-phenylpropanes and 1,3 diarylpyrazoles and their fragmentation under electron impact

Upon heating in the presence of arylamines 3-benzoyl-4-hydroxy-1-methyl-4- phenylpiperidine decyclizes via a retroaldol type reaction with subsequent transamination of the intermediate Mannich base to give 3-arylamino-1-oxo-1- phenylpropanes. In the case of the use of arylhydrazines this γ-piperidol recyclizes to give 1,3-diarylpyrazoles and their 4,5-dihydro derivatives. The mass spectroscopic behavior of a series of 3-arylamino-substituted 1-phenylpropanones has been studied.

Diastereoselective synthesis of 4-hydroxypiperidin-2-ones via Cu(I)-catalyzed reductive aldol cyclization

(Chemical Equation Presented) 4-Hydroxypiperidin-2-ones may be prepared in highly diastereoselective fashion using a Cu(I)-catalyzed reductive aldol cyclization of αβ-unsaturated amides with ketones. Used in combination with proline-catalyzed asymmetric M

Rare Earth Metal Complexes as Water-Tolerant Lewis Acid Catalysts in Organic Synthesis

Rare earth metal triflates are stable in aqueous media and can act as Lewis acid catalysts in several carbon-carbon bond forming reactions. This article describes some of these reactions; aldol and Mannich-type reactions in aqueous solution, and Friedel-Crafts acylations and Fries rearrangement in organic solvents. The reactions proceeded smoothly in the presence of a catalytic amount of the triflate under mild conditions. Moreover, the catalysts could be recovered after the reactions were completed and could be reused.