104581-57-9

Basic information

• Product Name: 5,5-diphenylpent-4-en-3-one
• Synonyms: 5,5-diphenylpent-4-en-3-one
• CAS NO: 104581-57-9
• Molecular Weight: 236.313
• Mol File: 104581-57-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 5,5-diphenylpent-4-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-diphenylpent-4-en-3-one(104581-57-9)
• EPA Substance Registry System: 5,5-diphenylpent-4-en-3-one(104581-57-9)

Safety Data

• Hazardous Substances Data: 104581-57-9(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 1629-58-9 4-penten-3-one 
• 3152-68-9 1-phenyl-pent-1-en-3-one 
• 27975-78-6 1-phenyl-1-pentyn-3-ol 
• 243867-57-4 2-methyl-3,3-diphenylcyclobutanone 
• 3152-68-9 (1E)-1-phenylpent-1-en-3-one 
• 778-66-5 1,1-diphenyl-1-propene 
• 243867-60-9 2,2-dichloro-3,3-diphenyl-4-methylcyclobutanone 
• 1116366-17-6 2-methylene-1,1-diphenylbutan-1-ol 
• 1312210-79-9 C₁₈H₂₀O₃ 

Relevant articles and documents

Palladium-catalyzed oxidative rearrangement of diaryl alkenyl carbinols to β,β-diaryl α,β-unsaturated ketones

An unusual oxidative palladium-catalyzed rearrangement of diaryl alkenyl carbinols to β,β-diaryl α,β-unsaturated ketones is described. The geometry of the alkene product is not determined by the electronic nature of the aryl substitutents but rather is determined by substitution pattern on the aryl rings. The reaction proceeds in good yields, utilizes oxygen at atmospheric pressure as the terminal oxidant, and tolerates a variety of functional groups on the aryl rings.

Reactivity in acid-catalyzed carbon-carbon heterolysis

Equilibrium and rate constants have been determined for the acid-catalyzed heterolysis of two alcohols, 9-xanthydrol and p-anisyldiphenylmethanol, and two sulfides, (9-xanthyl) methyl sulfide and (7-tropyl) methyl sulfide. These data together with literature information are compared with rate constants for acid-catalyzed C-C heterolysis of several (9-xanthyl) compounds, (7-tropyl) compounds, a set of 3-arylcyclobutanones, and two 2-arylnitrocyclopropanes, all of which fragment to carbocations plus a carbon-centered nucleofuge. The fragmentation mechanisms are shown to be A1 or A1(ion pair) except for the 2-arylnitrocyclopropanes which cleave in trifluoroacetic acid by a concerted mechanism. Rate comparisons among several unstrained substrate sets indicate that O-centered nucleofuges undergo acid-catalyzed heterolysis ca. 103-104 faster than S-centered nucleofuges and ca. 109-1014 faster than the C-centered nucleofuges used here. Factors assisting C-C heterolysis (and their effectiveness) include the acidity of the medium (strong); the basicity and nucleofugality of the nucleofuge (moderate); the stability of the electrofugic carbocation (strong); and relief of ring strain (enormous). Compared with acyclic cleavages, rate accelerations worth ca. 15 kcal/mol (for cyclobutanones) and ca. 27 kcal/mol (for nitrocyclopropanes) are found. These effects are discussed in terms of transition-state structure, aided by computational evidence.

THE-PALLADIUM-CATALYSED REDUCTIVE ADDITION OF ARYL IODIDES TO PROPARGYL ALCOHOLS: A ROUTE TO γ,γ-DIARYL ALLYLIC ALCOHOLS

The reaction of aryl iodides with ethynyl and arylethynyl, dialkyl carbinols in the presence of the tri- or dialkylammonium formate-palladium reagent provides a convenient route to γ,γ-diarylallylic alcohols.In the presence of arylethynyl, alkylcarbinols a lack of regioselectivity was observed and mixtures of β,γ-, γ,γ-diarylallylic alcohols, and α,β-unsaturated ketones were obtained.