63914-58-9

Basic information

• Product Name: 1,3-Propanedione, 2-methyl-1-(4-methylphenyl)-3-phenyl-
• CAS NO: 63914-58-9
• Molecular Formula: C17H16O2
• Molecular Weight: 252.313
• Mol File: 63914-58-9.mol

Chemical Properties

• CAS DataBase Reference: 1,3-Propanedione, 2-methyl-1-(4-methylphenyl)-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Propanedione, 2-methyl-1-(4-methylphenyl)-3-phenyl-(63914-58-9)
• EPA Substance Registry System: 1,3-Propanedione, 2-methyl-1-(4-methylphenyl)-3-phenyl-(63914-58-9)

Safety Data

• Hazardous Substances Data: 63914-58-9(Hazardous Substances Data)

Upstream product

• 25855-99-6 1-(4-methylphenyl)-3-phenyl-1,3-propanedione 
• 74-88-4 methyl iodide 
• 614-45-9 tert-Butyl peroxybenzoate 
• 201230-82-2 carbon monoxide 
• 106-38-7 para-bromotoluene 
• 93-55-0 1-phenyl-propan-1-one 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 106565-28-0 (1S,2S,3S/1R,2R,3R)-2-methyl-3-phenyl-1-p-tolyl-1,3-propanediol 
• 106565-27-9 (1R,2S,3R/1S,2R,3S)-2-methyl-3-phenyl-1-p-tolyl-1,3-propanediol 
• 106471-24-3 (1R,2S,3S/1S,2R,3R)-2-methyl-3-phenyl-1-p-tolyl-1,3-propanediol 
• 106565-29-1 (1R,2R,3S/1S,2S,3R)-2-methyl-3-phenyl-1-p-tolyl-1,3-propanediol 

Relevant articles and documents

Pd-catalyzed carbonylative α-arylation of aryl bromides: Scope and mechanistic studies

Reaction conditions for the three-component synthesis of aryl 1,3-diketones are reported applying the palladium-catalyzed carbonylative α-arylation of ketones with aryl bromides. The optimal conditions were found by using a catalytic system derived from [Pd(dba)2] (dba=dibenzylideneacetone) as the palladium source and 1,3-bis(diphenylphosphino)propane (DPPP) as the bidentate ligand. These transformations were run in the two-chamber reactor, COware, applying only 1.5 equivalents of carbon monoxide generated from the CO-releasing compound, 9-methylfluorene-9-carbonyl chloride (COgen). The methodology proved adaptable to a wide variety of aryl and heteroaryl bromides leading to a diverse range of aryl 1,3-diketones. A mechanistic investigation of this transformation relying on 31P and 13C NMR spectroscopy was undertaken to determine the possible catalytic pathway. Our results revealed that the combination of [Pd(dba)2] and DPPP was only reactive towards 4-bromoanisole in the presence of the sodium enolate of propiophenone suggesting that a [Pd(dppp)(enolate)] anion was initially generated before the oxidative-addition step. Subsequent CO insertion into an [Pd(Ar)(dppp)(enolate)] species provided the 1,3-diketone. These results indicate that a catalytic cycle, different from the classical carbonylation mechanism proposed by Heck, is operating. To investigate the effect of the dba ligand, the Pd0 precursor, [Pd(η3-1-PhC 3H4)(η5-C5H5)], was examined. In the presence of DPPP, and in contrast to [Pd(dba)2], its oxidative addition with 4-bromoanisole occurred smoothly providing the [PdBr(Ar)(dppp)] complex. After treatment with CO, the acyl complex [Pd(CO)Br(Ar)(dppp)] was generated, however, its treatment with the sodium enolate led exclusively to the acylated enol in high yield. Nevertheless, the carbonylative α-arylation of 4-bromoanisole with either catalytic or stoichiometric [Pd(η3-1-PhC3H4) (η5-C5H5)] over a short reaction time, led to the 1,3-diketone product. Because none of the acylated enol was detected, this implied that a similar mechanistic pathway is operating as that observed for the same transformation with [Pd(dba)2] as the Pd source. CO-operation is the key! The first palladium-catalyzed carbonylative α-arylation of aryl bromides is described. A wide array of different aryl 1,3-diketones can be isolated in good-to-excellent yields using only stoichiometric amounts of CO (see scheme). A mechanistic study is presented that suggests the need for enolate coordination prior to oxidative addition when [Pd(dba)2] is employed as the precatalyst. Copyright

Copper-catalyzed methylation of 1,3-diketones with tert-butyl peroxybenzoate

Copper-catalyzed radical methylation of 1,3-diketones with tert-butyl peroxybenzoate in air is described, providing a general pathway to α-methyl 1,3-diketones in moderate to good yields. This protocol has been scaled up to 50?g, and one of the synthesized products can be used in the synthesis of medicine, Rosuvastatin.

Method for preparing 2-methyl-1,3-dicarbonyl derivative

The invention discloses a method for preparing a 2-methyl-1,3-dicarbonyl derivative. A 1,3-dicarbonyl derivative serves as an initiator, raw materials are easy to obtain, and a great variety of raw materials are available. The product obtained through the method has high type diversity and can be used directly or used for other further reactions. Besides, only organic peroxides and a catalytic amount of inorganic copper salt are used, so that cost is low. According to the method, a reaction is conducted in air, reaction conditions are mild, pollution is small, reaction time is short, the yield of the target product is high, reaction operation and aftertreatment are easy, and the method is suitable for industrial production.

Palladium-catalyzed carbonylative α-arylation for accessing 1,3-diketones

With a hint of CO: The first Pd-catalyzed carbonylative α-arylations of simple ketones with carbon monoxide is presented for the direct synthesis of 1,3-diketones (see scheme). The method uses only stoichiometric amounts of CO, and hence allows for the si

Free radical ring expansion and chain extension of 1,3-diketones

Free radical-promoted one carbon ring expansion and chain extension of 1,3-diketones including 1,3-diarylpropane-1,3-diones and 2-aroyl-3,4-dihydro-2H- naphalen-1-one to generate corresponding 1,4-diketones are described.