17952-96-4

Usage

Uses

Used in Organic Synthesis:
3,5-diphenyl-4H-pyrazol-4-one 1,2-dioxide is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structure allows for versatile chemical reactions and modifications, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3,5-diphenyl-4H-pyrazol-4-one 1,2-dioxide is used as a starting material for the development of new pharmaceutical drugs. Its structural features and potential biological activities make it an attractive candidate for the design and synthesis of novel therapeutic agents.
Used in Antioxidant Applications:
3,5-diphenyl-4H-pyrazol-4-one 1,2-dioxide is used as an antioxidant agent to protect cells and tissues from oxidative damage caused by reactive oxygen species. Its antioxidant properties can be harnessed in the development of nutraceuticals, cosmeceuticals, and pharmaceuticals to promote health and prevent various diseases associated with oxidative stress.
Used in Antimicrobial Applications:
3,5-diphenyl-4H-pyrazol-4-one 1,2-dioxide is also used as an antimicrobial agent to combat bacterial and fungal infections. Its antimicrobial properties can be utilized in the development of new antibiotics, antifungal agents, and disinfectants to address the growing concerns of antibiotic resistance and the need for novel antimicrobial therapies.
Used in Pharmaceutical Drug Development:
3,5-diphenyl-4H-pyrazol-4-one 1,2-dioxide serves as a promising scaffold for the development of new pharmaceutical drugs. Its unique structure and potential biological activities make it a valuable template for the design and synthesis of innovative therapeutic agents targeting various diseases and conditions.

Upstream product

• 21067-42-5 1,3-diphenyl-2-propen-1-one oxime 

Downstream Products

• 144951-17-7 C₂₅H₁₈N₂O₄ 
• 34765-45-2 1-methyl-3,5-diphenyl-4-acetoxypyrazole 
• 35228-99-0 3,5-diphenyl-1-methyl-4-pyrazolol 
• 49661-64-5 dimethyl (1-methyl-3,5-diphenyl-4-pyrazolyl)phosphate 
• 26732-97-8 4-oxo-6-oxy-3a,5-diphenyl-2,3,3a,4-tetrahydro-pyrazolo[1,5-b]isoxazole-2-carboxylic acid methyl ester 
• 26732-98-9 2-butoxy-6-oxy-3a,5-diphenyl-3,3a-dihydro-2H-pyrazolo[1,5-b]isoxazol-4-one 
• 71964-79-9 7a-morpholin-4-yl-1-oxy-2,3a-diphenyl-3b,4,5,6,7,7a-hexahydro-3aH-benzo[d]pyrazolo[1,5-b]isoxazol-3-one 
• 71964-78-8 1-oxy-2,3a-diphenyl-7a-piperidin-1-yl-3b,4,5,6,7,7a-hexahydro-3aH-benzo[d]pyrazolo[1,5-b]isoxazol-3-one 
• 71964-81-3 1-oxy-2,3a-diphenyl-7a-pyrrolidin-1-yl-3b,4,5,6,7,7a-hexahydro-3aH-benzo[d]pyrazolo[1,5-b]isoxazol-3-one 

Relevant academic research and scientific papers

Stereochemical Effects in the Nitrosation of Some α,β-Unsaturated Ketoximes. Formation of 1-Hydroxypyrazole 2-Oxides and 4-Oximino-4,5-dihydroisoxazoles

Several α,β-unsaturated ketoximes R1CH=CHC(=NOH)R2 were nitrosated using butyl nitrite in aqueous ethanol in the presence of copper(II) sulfate and pyridine.The product distribution varied depending on whether the oxime hydroxyl group was syn or anti with respect to the carbon-carbon double bond.The anti-oximes gave the copper complexes of 1-hydroxypyrazole 2-oxides in high yields.The isomeric syn-oximes gave lower yields of the pyrazole complexes along with 4-oximino-4,5-dihydroisoxazole derivatives.For the syn-oximes where R1 is phenyl and R2 is either methyl or ethyl, conversion of the oximes to the parent ketones was also observed.The results may be explained by processes involving N-nitrosonitrone intermediates.

Nitrosation of Methyl and Phenyl Styryl Ketoximes Under Oxygen. Formation of 4-Nitro-1-hydroxypyrazole 2-Oxides and 3,5-Diphenyl-4-nitrato-4,5-dihydroisoxazole

The nitrosation of the oximes of 4-phenyl-3-buten-2-one and 1,3-diphenyl-2-propen-1-one under oxygen has been reinvestigated.In addition to 4-oxo- and 4-oximino-4H-pyrazole 1,2-dioxides previously reported, the reactions give 4-nitro-1-hydroxypyrazole 2-oxides.In the case of 1,3-diphenyl-2-propen-1-one oxime the nitrosation reaction also gives 3,5-diphenyl-4-nitrato-4,5-dihydroisoxazole.Evidence is presented suggesting that the nitrate ester is formed through the rearrangement of a peroxynitrite intermediate.

Preparation of 4-Bromo-1-hydroxypyrazole 2-Oxides by Nitrosation of α-Bromo-α,β-unsaturated Ketoximes

Nitrosation of the oximes of 3-bromo-3-penten-2-one, 3-bromo-4-phenyl-3-buten-2-one, and 2-bromo-1,3-diphenyl-2-propen-1-one using sodium nitrite in acetic acid gave low yields of 4-pyrazolone 1,2-dioxides.Nitrosation using butyl nitrite in the presence of copper(II) sulfate and pyridine in aqueous ethanol produced insoluble copper complexes from which 3,5-dimethyl-, 3-methyl-5-phenyl-, and 3,5-diphenyl-4-bromo-1-hydroxypyrazole 2-oxides could be liberated by treatment with dilute potassium hydroxide, filtration, and acidification of the filtrate.High yields wereobtained with the first two oximes, but, presumably due to unfavorable stereochemistry of the oxime, the diphenyl derivative gave a lower yield of the complex, accompanied by 4-bromo- and 4-nitro-3,5-diphenylisoxazole and 4-oximino-3,5-diphenyl-4,5-dihydroisoxazole.