28746-58-9

Basic information

• Product Name: 1,3-Cyclohexanedione, 5,5-dimethyl-2-(phenylmethylene)-
• Synonyms: AmbscSP-59;2-benzylidenedimedone
• CAS NO: 28746-58-9
• Molecular Formula: C15H16O2
• Molecular Weight: 228.291
• Mol File: 28746-58-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 386.0±42.0 °C(Predicted)
• Density: 1?+-.0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,3-Cyclohexanedione, 5,5-dimethyl-2-(phenylmethylene)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclohexanedione, 5,5-dimethyl-2-(phenylmethylene)-(28746-58-9)
• EPA Substance Registry System: 1,3-Cyclohexanedione, 5,5-dimethyl-2-(phenylmethylene)-(28746-58-9)

Safety Data

• Hazardous Substances Data: 28746-58-9(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 126-81-8 dimedone 
• 3376-23-6 N-methyl-α-phenylnitrone 

Downstream Products

• 1159509-05-3 7,8-dihydroxy-3,3-dimethyl-9-phenyl-2,3,4,9-tetrahydroxanthen-1-one 
• 1159509-06-4 5,8-dihydroxy-3,3-dimethyl-9-phenyl-2,3,4,9-tetrahydroxanthen-1-one 
• 1176087-22-1 7,7-dimethyl-10-phenyl-6,7,8,10-tetrahydropyrimido[5,4-b]quinoline-2,4,9(1H,3H,5H)-trione 
• 421586-21-2 6,6-dimethyl-9-phenyl-5,6,7,9-tetrahydro-[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one 
• 107752-97-6 2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 1309477-28-8 10,10-dimethyl-7-phenyl-7,9,10,11-tetrahydro-6H,8H-chromeno[4,3-b]chromene-6,8-dione 
• 722483-58-1 3,7,7-trimethyl-4-phenyl-4,7,8,9-tetrahydroisoxazolo[5,4-b]quinolin-5(6H)-one 
• 1372100-48-5 10,10-dimethyl-7-phenyl-7,10,11,12-tetrahydro-6H-chromeno[4,3-b]quinoline-6,8(9H)-dione 
• 872410-93-0 2-amino-6,6-dimethyl-9-phenyl-5,6,7,9-tetrahydro[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one 

Relevant articles and documents

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A new type IV DES: a competent green catalyst and solvent for the synthesis of α,β-unsaturated diketones and dicyano compounds by Knoevenagel condensation reaction

DESs are new and greener alternatives to ionic liquids formed by mixing components that are capable of forming hydrogen bonds between them. The strong hydrogen bond interactions between the constituents make a large depression in the melting points compared to pure constituents. They are emerging as green solvents and have loomed as adorable alternatives to conventional organic solvents and ionic liquids with unique properties. In the present article, four new CeCl3·7H2O-based DESs were developed and their physical properties were studied. Their activities were checked in the Knoevenagel condensation reaction of dimedone/malononitrile with various aldehydes. The recyclability of the catalyst/solvent was achieved up to five runs without much change in the activity.

Synthesis of heterocyclic compounds derived from dimedone and their anti-tumor and tyrosine kinase inhibitions

The reaction of dimedone with arylaldehydes gave the benzylidene derivatives 3a-c, the latter underwent a series of heterocyclization reactions to give fused thiophene, pyrazole isoxazole and pyridazine derivatives. The synthesized compounds were evaluated against different kinds of cancer cell lines together tyrosine kinases and Pim-1 kinase inhibitions. All the synthesized compounds were assessed for the inhibitory activities against A549 (non-small cell lung cancer), H460 (human lung cancer), HT-29 (human colon cancer) and MKN-45 (human gastric cancer) cancer cell lines together with foretinib as the positive control by a MTT assay. The promising compounds were 3c, 5b, 5e, 5f, 7c, 7f, 9c, 11b, 12c, 12d, 13b, 13d, 14b, 16c and 16d among the tested compounds. On the other hand, compounds 5b, 5e, 5f, 7c, 11b, 12c, 12d, 13d, 14b, 16c and 16d were the most effective inhibitors against tyrosine kinases and compounds 5b, 11b, 12d, 13d, 14b and 16c were the most potent against Pim-1 kinase.