51307-04-1

Basic information

• Product Name: 2,4-Pentanedione, 1,5-diphenyl-
• Synonyms: 1,5-diphenyl-pentane-2,4-dione;2,4-Pentanedione,1,5-diphenyl;dibenzoylmethane;1,5-Diphenyl-pentan-2,4-dion;1,3-dibenzyl-1,3-propanedione;1,5-diphenyl-2,4-pentanedione
• CAS NO: 51307-04-1
• Molecular Formula: C17H16O2
• Molecular Weight: 252.313
• Mol File: 51307-04-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2,4-Pentanedione, 1,5-diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pentanedione, 1,5-diphenyl-(51307-04-1)
• EPA Substance Registry System: 2,4-Pentanedione, 1,5-diphenyl-(51307-04-1)

Safety Data

• Hazardous Substances Data: 51307-04-1(Hazardous Substances Data)

Usage

General Description

2,4-Pentanedione, 1,5-diphenyl- is a chemical compound with the molecular formula C17H16O2. It is also known by the trade name acetylacetone, and is an organic compound that is used in the production of various other chemicals and materials. It is commonly used as a complexing agent in the production of metal ions and as a precursor in the synthesis of heterocycles. Additionally, 2,4-Pentanedione, 1,5-diphenyl- is used in the production of pharmaceuticals, dyes, and as a flavoring agent in food products. It is also known to exhibit mild irritant properties and should be handled with care.

Upstream product

• 101-97-3 Ethyl 2-phenylethanoate 
• 103-79-7 1-phenyl-acetone 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 109839-21-6 3-phenyl-2,4-hexanedione 
• 20268-21-7 (E)-2-phenylacetaldehyde oxime 
• 300-57-2 allylbenzene 
• 161152-04-1 3-(dimethyl-λ4-sulfanylidene)-1,5-diphenyl-pentane-2,4-dione 
• 504-64-3 carbon suboxide 
• 6921-34-2 benzylmagnesium chloride 
• 103-80-0 phenylacetyl chloride 
• 123-54-6 acetylacetone 
• 1007-32-5 benzyl ethyl ketone 
• 141-78-6 ethyl acetate 
• 110029-55-5 2-benzyl-2-hydroxy-4-oxo-5-phenyl-valeric acid 

Downstream Products

• 107772-71-4 3,5-dibenzyl-pyrazole-1-carboxylic acid amide 
• 1450605-92-1 5-amino-3-phenylmethylisoquinolin-1-one 
• 1450605-82-9 5-nitro-3-phenylmethylisoquinolin-1-one 
• 1450605-72-7 5-nitro-3-phenylmethylisocoumarin 
• 1036388-86-9 (5,14-dihydro-6,8,15,17-tetrabenzyldibenzo[b,i][1,4,8,11]tetracyclodecine)nickel(II) 
• 135943-83-8 (2S,4S)-1,5-diphenyl-2,4-pentanediol 
• 135943-84-9 (2R,4R)-1,5-diphenyl-2,4-pentanediol 
• 205116-63-8 3-Dimethylaminomethylene-1,5-diphenyl-pentane-2,4-dione 
• 51307-23-4 1,5-Diphenyl-3-oximino-2,4-pentandion 
• 19311-79-6 1-methyl-3,5-diphenyl-1H-pyrazole 
• 259228-88-1 (R,R)-1,5-diphenyl-2,4-pentanediol cyclic sulfate 

Relevant articles and documents

One-pot tandem Hurtley-retro-Claisen-cyclisation reactions in the synthesis of 3-substituted analogues of 5-aminoisoquinolin-1-one (5-AIQ), a water-soluble inhibitor of PARPs

Poly(ADP-ribose)polymerase-1 (PARP-1) is an important target for drug design for several therapeutic applications. 5-Aminoisoquinolin-1-one (5-AIQ) is a highly water-soluble lead compound; synthetic routes to 3-substituted analogues were explored. Tandem Hurtley coupling of β-diketones with 2-bromo-3-nitrobenzoic acid, retro-Claisen acyl cleavage and cyclisation gave the corresponding 3-substituted 5-nitroisocoumarins. Treatment with ammonia at high temperature and reduction with tin(II) chloride gave eleven target 3-substituted 5-AIQs, which were all soluble in water (>1% w/v) as their HCl salts. Most were more potent than 5-AIQ as inhibitors of PARP-1 and of PARP-2 in vitro, the most active being 5-amino-3-methylisoquinolin-1-one (PARP-1: IC 50 = 0.23 μM vs IC50 = 1.6 μM for 5-AIQ). Some rationalisation of the SAR was achieved through molecular modelling.

Method for preparing chiral diphosphines

The invention concerns a method for preparing a compound of formula (1) wherein: A represents naphthyl or phenyl optionally substituted; and Ar1, Ar2independently represent a saturated or aromatic carbocyclic group, optionally substituted.

3-Unsubstituted 1,5-diaryl-2,4-pentanediones and -4-methoxy-2-pentanones: Synthesis via corresponding 3-hydroxy ketones generated from 2-isoxazolines

Aryl acetaldoximes are reacted with allylarenes in the presence of sodium hypochlorite to give 3,5-bis(arylmethyl)-2-isoxazolines which are then converted to 1,5-diaryl-4-hydroxy-2-pentanones by a reductive hydrogenation in the presence of water. These in