5409-60-9

Usage

Uses

Used in Chemical Synthesis:
4,4-Diphenyl-2-butanone is used as a reagent for the efficient synthesis and ring-opening reactions of monofluorinated epoxides. Its unique structure allows it to participate in various chemical reactions, making it a versatile compound in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4,4-Diphenyl-2-butanone is used as an intermediate in the synthesis of various drugs and pharmaceutical compounds. Its reactivity and structural properties make it a valuable component in the development of new medications.
Used in Research and Development:
4,4-Diphenyl-2-butanone is also utilized in research and development for the study of chemical reactions and the development of new synthetic methods. Its unique properties and reactivity make it an essential tool for chemists and researchers in the field of organic chemistry.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 4213, 1973 DOI: 10.1021/jo00963a030Synthesis, p. 575, 1984Tetrahedron Letters, 20, p. 4591, 1979

Upstream product

• 19289-28-2 ethyl 2-benzhydryl-3-oxobutanoate 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 1896-62-4 (E)-benzalacetone 
• 71-43-2 benzene 
• 23074-57-9 4-ethoxybut-3-en-2-one 
• 118217-47-3 3-oxo-5,5-diphenylpentanoic acid ethylester 
• 591-50-4 iodobenzene 
• 78-94-4 methyl vinyl ketone 
• 591-51-5 phenyllithium 
• 14922-16-8 phenylazo phenyl sulfone 
• 100-56-1 phenylmercury(II) chloride 
• 3220-49-3 phenyl copper 
• 143-66-8 sodium tetraphenyl borate 
• 603-36-1 triphenylantimony 

Downstream Products

• 110246-10-1 1-(1-methyl-3,3-diphenyl-propyl)-piperidine 
• 29869-78-1 methyl-(1-methyl-3,3-diphenyl-propyl)-amine 
• 65190-71-8 [2-(2,2-diphenyl-ethyl)-[4]quinolyl]-phenyl-amine 
• 36317-57-4 4,4-diphenyl-butan-2-one oxime 
• 146537-63-5 1,5-diphenyl-2,4-pentadien-1-one oxime 
• 13957-55-6 recipavrin 
• 101596-92-3 3-oxo-5,5-diphenyl-valeraldehyde 
• 96774-06-0 6-tert-Butyl-2,4-dimethyl-3-[2-(1-methyl-3,3-diphenyl-propylamino)-ethyl]-phenol 
• 32780-78-2 5-[1-hydroxy-2-(1-methyl-3,3-diphenylpropyl)aminoethyl]salicylamide 
• 29869-77-0 4,4-diphenyl-2-butanamine 
• 1027324-14-6 1-Bromo-4,4-diphenyl-butan-2-ol 
• 29869-86-1 4-(4-chlorophenyl)-4-phenylbutane-2-one 
• 120467-71-2 4,4-bis(4-chlorophenyl)butan-2-one 
• 36317-60-9 4,4-diphenyl-2-butanol 

Relevant academic research and scientific papers

Transannular anti-Michael addition: formation of 4H-pyrazolo[5,1-c]thiazines

The reaction of 2-(diphenylmethylene)thietan-3-one (2) with 1,2,4,5-tetrazines (3a-c) in KOH/MeOH/THF gives 4H-pyrazolo[5,1-c]thiazines (7a-c). This novel condensation reaction proceeds via the intermediacy of an 8-(diphenylmethylene)-2H-1,4,5-thiadiazocin-7(8H)-one (5), which undergoes a multi-step rearrangement including a rare anti-Michael addition.

Arylboronic Acid Catalyzed Dehydrative Mono-/Dialkylation Reactions of β-Ketoacids and Alcohols

The dehydrative mono-/dialkylation reactions of alcohols and β-ketoacids were realized under arylboronic acid catalysis, furnishing a series of β-aryl ketones and β-ketoesters in yields of 15–99%, with CO2 and H2O being the byproduct

Beyond the Tebbe Olefination: Direct Transformation of Esters into Ketones or Alkenes

A direct, effective, and operationally simple transformation of esters into ketones or alkenes by the exclusive action of Tebbe's reagent has been developed. The transformation utilizes the dual character of Tebbe's reagent as both a methylenation agent and a rearrangement catalyst in the reaction of a wide range of substituted vinyl ethers. The resulting transformation involves sequential methylenation and rearrangement reactions and it offers a high degree of selectivity toward the synthesis of ketones or alkenes. The scope and limitations of the developed methods have been also examined.

Photocatalytic Hydroacylation of Alkenes by Directly Using Acyl Oximes

Acyl oximes are directly used as the acyl radical precursors in the hydroacylation reactions for the first time. In this work, acyl radicals can be effectively generated via β-scission of a phosphoranyl radical under photocatalytic conditions. As a result, the hydroacylation of alkenes triggered by the resulting acyl radicals leads to facile syntheses of a range of valuable ketones.

Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes to Generate Dialkyl Ketones

A general protocol for the hydroacylation of styrenes from aliphatic carboxylic acids is reported. These reactions proceed via β-scission of a phosphoranyl radical that is accessed by photoredox catalysis, followed by addition of the resulting acyl radical to the styrenyl olefin. We show that phosphine tunability is critical for efficient intermolecular coupling due to competitive quenching of the photocatalyst by the olefin. Primary, secondary, and structurally rigid tertiary carboxylic acids all generate valuable unsymmetrical dialkyl ketones.

Rhenium-catalyzed α-alkylation of enol acetates with alcohols or ethers

When benzylic and allylic alcohols were treated with enol acetate in the presence of a catalytic amount of a rhenium complex, ReBr(CO)5, the carbon-carbon bond formation of the alcohols and enol acetate smoothly proceeded to give the corresponding ketones and aldehyde in moderate to good yields. For the reaction of allylic alcohols, γ,δ-unsaturated carbonyl compounds were obtained in good yields. When ethers were used instead of alcohols as the alkylated agent, two alkyl moieties on the ethers were utilized on the reaction.

Two efficient pathways for the synthesis of aryl ketones catalyzed by phosphorus-free palladium catalysts

Allylic alcohols, 1-buten-3-ol, 1-penten-3-ol and 1-octen-3-ol, reacted with aryl iodides (iodotoluene, 4-iodotoluene, 4-iodophenol and 4-iodanisole) under Heck reaction conditions to form corresponding saturated aryl ketones in one step. The same products were obtained in a two-step tandem reaction consisted of the Heck coupling of allylic alcohols with aryl iodides, followed by hydrogenation. Reactions were catalyzed by phosphorus-free palladium precursors modified with the menthol-substituted imidazolium chlorides. Formation of crystalline palladium nanoparticles, of the diameter up to 65 nm, in the reaction mixture was evidenced by TEM.

Hydrotalcite-supported palladium nanoparticles as catalysts for the hydroarylation of carbon-carbon multiple bonds

Palladium nanoparticles supported on Mg/Ca hydrotalcites catalyze the hydroarylation reaction of different alkynes and alkenes with aryl iodides under air in MeCN. The reaction of tertiary propargylic alcohols (1) with aryl iodides (2) yields, stereoselectively, γ,γ-diarylallylic alcohols (3) in moderate to high yields and high selectivity. Also, the HT/Pd hydroarylation reaction with aryl iodides was attempted on norbornene and α,β-unsaturated ketones affording, respectively, exo-aryl bicyclo[2.2.1]heptanes and β-aryl ketones in moderate to high yields. All the reactions described benefit from using a heterogeneous catalyst with evident advantages in terms of reaction purification and recyclability of the catalyst.

Diastereoselective synthesis of β-amino ketone and acid derivatives by palladium-catalyzed conjugate addition

The first diastereoselective synthesis of β-amino ketone and β-amino acid derivatives by palladium-catalyzed conjugate addition of arylboronic acids to chiral β-enamino ketones and β-enamino esters is reported. The catalytic system employing (S)-4-(tert-butyl)oxazolidin-2-one as the chiral auxiliary in water under an air atmosphere provides β-amino ketone and β-amino acid derivatives in high yields with excellent diastereoselectivity.

Palladium-catalyzed site-selective arylation of aliphatic ketones enabled by a transient ligand

Transition metal-catalyzed direct C-H bond functionalization enabled by transient ligands has become an attractive topic. Here we report a palladium-catalyzed site-selective arylation of β-C(sp3)-H bonds in aliphatic ketones with β-alanine as the transient ligand.