27547-08-6

Usage

InChI:InChI=1/C16H13ClO3/c1-19-13-8-4-10(5-9-13)14(18)16-15(20-16)11-2-6-12(17)7-3-11/h2-9,15-16H,1H3

Upstream product

• 6552-68-7 4'-methoxy-4-chlorochalcone 
• 6552-68-7 4-chloro-4'-methoxy-chalcone 
• 1073-67-2 4-vinylbenzyl chloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 52578-07-1 2-p-Chlorphenyl-3-p-anisyl-3-oxopropanal 
• 125968-58-3 2-hydrazino-4-(p-methoxyphenyl)-6-(p-chlorophenyl)pyrimidine 
• 52578-11-7 2-(4-chlorophenyl)-1-(4-methoxyphenyl)ethanone 

Relevant academic research and scientific papers

Oxidative coupling of alkenes with aldehydes and hydroperoxides: One-pot synthesis of 2,3-epoxy Ketones

A new transition metal-free oxidative coupling of unactivated terminal alkenes with aldehydes and hydroperoxides in the presence of 10 mol% potassium tert-butanolate (t-BuOK) is described thereby realizing trifunctionalization of alkenes toward 2,3-epoxy ketones. This method is applicable to a wide range of aldehydes, including aryl and alkyl aldehydes, with excellent functional group tolerance, and provides for the one-step assembly of 2,3-epoxy ketones.

Visible-Light-Promoted Photoredox Syntheses of α,β-Epoxy Ketones from Styrenes and Benzaldehydes under Alkaline Conditions

A range of styrenes and benzaldehydes were smoothly combined to form α,β-epoxy ketones under the synergistic actions of photocatalyst Ru(bpy)3Cl2, tert-butyl hydroperoxide (t-BuOOH), cesium carbonate (Cs2CO3), and visible light irradiation. The process likely proceeds through visible-light-enabled photocatalytic generations of acyl radicals as key intermediates.

One-pot synthesis of chalcone epoxides - A green chemistry strategy

Waste minimization is a very important aspect of an environmentally benign protocol. A one-pot consecutive process has been developed for chalcone epoxide synthesis that allows compounds to be prepared without having to isolate and purify the intermediates. The strategy utilizes consecutive Claisen Schmidt condensation and epoxidation reactions to prepare chalcone epoxides from substituted benzaldehydes and acetophenones in good yields.

Ring opening of α,β-epoxy phenyl ketones with eerie ammonium nitrate (CAN) and potassium bromide

Ring-opening reaction of α,β-epoxy phenyl ketones was achieved cooperatively using cerium ammonium nitrate (CAN) and potassium bromide. The reaction occurred regioselectively at the β-C to afford syn-β-bromo-α-hydroxyl ketones as main outcomes.

Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)- 3(trifluoromethyl)-1h-pyrazol-1-yl]benzenesulfonamide (sc-58635, celecoxib)

A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC- 236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of 1i (4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-y1]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.