131348-67-9

Basic information

• Product Name: 1,5-diphenyl-1,4-pentadien-3-one
• CAS NO: 131348-67-9
• Molecular Weight: 234.298
• Mol File: 131348-67-9.mol

Chemical Properties

• CAS DataBase Reference: 1,5-diphenyl-1,4-pentadien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-diphenyl-1,4-pentadien-3-one(131348-67-9)
• EPA Substance Registry System: 1,5-diphenyl-1,4-pentadien-3-one(131348-67-9)

Safety Data

• Hazardous Substances Data: 131348-67-9(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 1896-62-4 (E)-benzalacetone 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 38986-89-9 3-phenylacryloyl fluoride 
• 13433-42-6 dimethyl α-trimethylsilylmethylphosphonate 
• 875877-88-6 (2E)-[[3-phenyl-1-(phenylethynyl)-2-propenyl]oxy]-trimethylsilane 
• 67-64-1 acetone 
• 113847-99-7 (4-Hydroxy-2-oxo-4-phenyl-butyl)-phosphonic acid diethyl ester 
• 854029-40-6 4,5-dibromo-1,5-diphenyl-pent-1-en-3-one 

Downstream Products

• 1415391-60-4 (E)-ethyl 2,5-dioxo-3,7-diphenylhept-6-enoate 
• 1415391-73-9 (2R,3R,E)-ethyl 2-hydroxy-5-oxo-3,7-diphenylhept-6-enoate 
• 1132957-67-5 (E)-1-(2-hydroxy-4,5-diphenyl-2-(E)-styrylcyclopentyl)-3-phenylprop-2-en-1-one 
• 1055325-79-5 6-phenyl-4-styryl-cyclohexa-1,3-dienecarboxylic acid methyl ester 

Relevant articles and documents

Stereoselective debromination of vic-dibromides to E-alkenes with dimethylformamide

A simple and efficient procedure for the quantitative debromination of vic-dibromides to E-alkenes in refluxing dimethylformamide has been described.

Stereoselective synthesis, spectral characterization, docking and biological screening of coumarin derivatives

The compounds being synthesized in present research are chiral in nature so for getting enantiopure compounds, stereoselective synthesis was carried out by organocatalysis. The importance of enantiopure compounds can not be overstated because the living systems are chiral in nature and response of enantiomers can be very different in living systems. The organocatalysed synthesis was accumplished using 4-hydroxycoumarin and variously substituted dibenzylideneacetones as reactants and the organocatalyst being used was 9-amino-9-deoxyepiquinine. The range of enantioselectivity achieved was 24-95%. The synthesized compounds were characterized by UV, IR, 1H NMR, 13C NMR, EIMS, UVCD, VCD and Chiral HPLC. The major focus of this research was to develop anticoagulant compounds and therefore the molecular docking studies were carried out with crystal structure of vitamin k epoxide reductase (3kp9) and then screened for in-vitro anticoagulant activity by using warfarin as positive control. Out of six synthesized compounds, four compounds (1,2,5,6) have shown greater binding affinity with 3kp9 than warfarin. In in-vitro anticoagulant studies, all compounds showed improved IC50 values than warfarin. Besides anticoagulant activity, antimocrobial activities were also carried out with six different strains of bacteria and fungi. Compound (5) showed 79% inhibition against Bacillus subtillis and 62 % inhibition against Staphylococcus aureus.

Exploration of synthetic antioxidant flavonoid analogs as acetylcholinesterase inhibitors: an approach towards finding their quantitative structure–activity relationship

The binding interactions between acetylcholinesterase (AChE) and a series of antioxidant flavonoid analogs were studied by fluorescence spectroscopic assay. The present study incorporated different classes of naturally occurring and synthetic flavonoid compounds like flavones, isoflavones, and chalcones as well as a few standard antioxidants. The AChE inhibitory (AChEI) activity of these compounds was further analyzed using in silico techniques, namely pharmacophore mapping, quantitative structure–activity relationship (QSAR) analysis, and molecular docking studies. We have also compared the AChE inhibitory and radical scavenging antioxidant activities of these compounds. Both the AChE inhibitory and antioxidant activities of these compounds were found to be highly dependent on their structural patterns. However, it was observed that, in general, flavones are comparatively better AChE inhibitors as well as antioxidants compared to chalcones. [Figure not available: see fulltext.].

Gram-scale preparation of dialkylideneacetones through Ca(OH)2-catalyzed Claisen-Schmidt condensation in dilute aqueous EtOH

A synthetic method of dialkylideneacetones has been developed. Compared with known protocols, the method employed catalytic Ca(OH)2 as the cheap, mild base catalyst and dilute aqueous EtOH (20%, v/v) as the green and safe solvent. The procedure was easily operated: In most cases, the product could be isolated by a simple filtration, and purified by washing with water. This paper provided experimental details of the reactions, which could be applied in gram-scale synthesis and should be a very reliable and practical protocol to prepare these useful compounds in laboratory and at the industrial level.

Copper-catalyzed rearrangement of N-aryl nitrones into epoxyketimines

Please pass the oxygen: A new method for the preparation of trans-α,β-epoxyketimines has been achieved through a copper-catalyzed rearrangement of (E)-α,β-unsaturated nitrones. The scope and tolerance of the method is evaluated and the synthetic utility of the products is demonstrated. The new transformation provides facile access to an unusual, densely functionalized intermediate that can be exploited for further synthetic application. Copyright

Novel one-pot three-component coupling reaction with trimethylsilylmethyl- phosphonate, acyl fluoride, and aldehyde through the horner-wadsworth-emmons reaction

A novel three-component coupling between trimethylsilylmethylphosphonate, acyl fluoride, and aldehyde has been developed. A sequential nucleophilic addition of lithio-trimethylsilylmethylphosphonate to the acyl fluoride and Horner-Wadsworth-Emmons reaction of an aldehyde with the lithio-β- ketophosphonate generated in situ by desilylation at the α-position of the α-silyl-β-ketophosphonate by fluoride took place cleanly in a one-pot operation. Various E- and Z-enones were obtained in high yields with high stereoselectivities by this one-pot procedure.

Convenient stereoselective synthesis of (Z)-chalcone derivatives from 1,3-diaryl-2-propynyl silyl ethers

Various (Z)-chalcone derivatives were easily synthesized in a stereoselective manner from 1,3-diaryl-2-propynyl silyl ethers by a catalytic reaction using potassium tert-butoxide under very mild conditions after acid treatment.

Larvicidal studies of chalcones and their derivatives

Chalcone (1,3-diphenyl-2-propen-1-one) is considered as the lead compound among all the chalcone type compounds used for the larvicidal studies, as it has the highest toxicity against the larvae of Culex quinquefasciatus. 4-Phenylbut-3-en-2-one, where a methyl group replaces the phenyl group of chalcone, is less active than chalcone; but still has higher activity than other derived compounds except the oxime of the same compound, while 1,5-diphenylpenta-1,4-dien-3-one (in which the lengthening of the acyclic conjugated portion occurs) has almost no activity at 100 ppm at an interval of 24 h. ANOVA and CD values of the compounds show that larvicidal activity of 4-phenylbut-3-en-2-one and its oxime is greater than its phenylhydrazone, which has, however, higher activity than that of semicarbazone of 4-phenylbut-3-en-2- one. On the other hand the activities of 1,5-diphenylpenta-1,4-dien-3-one itself and 2,4-dinitrophenylhydrazone of chalcone and chalcone type compounds are almost nil at 100 ppm concentration at an interval of 24 h at 30 ± 2°C. The probable explanation of the fall of larvicidal activities of these compounds has been presented.

Chemoselective and stereoselective debromination of vicinal-dibromides with sodium dithionite

A simple and efficient procedure for the quantitative debromination of vic-dibromides has been reported with sodium dithionite at ambient temperature. These eliminations are chemoselective and also stereoselective.