99059-05-9

Upstream product

• 66581-99-5 2-hydroxy-5-cyanomethylphenylethan-2-one 
• 30787-43-0 5'-(chloromethyl)-2'-hydroxyacetophenone 
• 118-93-4 o-hydroxyacetophenone 
• 1292299-20-7 2-acetyl-4-(2-diazoacetyl)phenyl acetate 
• 1292299-21-8 1-(3-acetyl-4-hydroxyphenyl)-2-diazoethanone 
• 1292298-94-2 2-(3-acetyl-4-hydroxyphenyl)-2-oxoethyl diethyl phosphate 
• 16357-40-7 3-acetyl-4-hydroxybenzoic acid 
• 70829-27-5 4-acetoxy-3-acetylbenzoic acid 
• 99-96-7 4-hydroxy-benzoic acid 

Downstream Products

• 109697-13-4 [4-hydroxy-3-(3,4-methylenedioxy-trans-cinnamoyl)-phenyl]-acetic acid 
• 101451-67-6 (3-trans-cinnamoyl-4-hydroxy-phenyl)-acetic acid 
• 101451-72-3 (4-oxo-2-phenyl-chroman-6-yl)-acetic acid 
• 368879-02-1 [3-bromo-4-hydroxy-5-(3-phenyl-propionyl)-phenyl]-acetic acid 
• 101451-67-6 {4-Hydroxy-3-[(E)-(3-phenyl-acryloyl)]-phenyl}-acetic acid 

Relevant academic research and scientific papers

Flavone acetic acid derivatives, pharmaceutical composition thereof as well as preparation methods and applications of flavone acetic acid derivatives and pharmaceutical composition

The invention belongs to the field of medication chemistry, and relates to flavone acetic acid derivatives, pharmaceutical composition thereof as well as preparation methods and applications of the flavone acetic acid derivatives and the pharmaceutical co

2-Diazo-1-(4-hydroxyphenyl)ethanone: A versatile photochemical and synthetic reagent

α-Diazo arylketones are well-known substrates for Wolff rearrangement to phenylacetic acids through a ketene intermediate by either thermal or photochemical activation. Likewise, α-substituted p-hydroxyphenacyl (pHP) esters are substrates for photo-Favorskii rearrangements to phenylacetic acids by a different pathway that purportedly involves a cyclopropanone intermediate. In this paper, we show that the photolysis of a series of α-diazo-p- hydroxyacetophenones and p-hydroxyphenacyl (pHP) α-esters both generate the identical rearranged phenylacetates as major products. Since α-diazo-p-hydroxyacetophenone (1a, pHP N2) contains all the necessary functionalities for either Wolff or Favorskii rearrangement, we were prompted to probe this intriguing mechanistic dichotomy under conditions favorable to the photo-Favorskii rearrangement, i.e., photolysis in hydroxylic media. An investigation of the mechanism for conversion of 1a to p-hydroxyphenyl acetic acid (4a) using time-resolved infrared (TRIR) spectroscopy clearly demonstrates the formation of a ketene intermediate that is subsequently trapped by solvent or nucleophiles. The photoreaction of 1a is quenched by oxygen and sensitized by triplet sensitizers and the quantum yields for 1a-c range from 0.19 to a robust 0.25. The lifetime of the triplet, determined by Stern-Volmer quenching, is 31 ns with a rate for appearance of 4a of k = 7.1 × 10 6 s-1 in aq. acetonitrile (1:1 v:v). These studies establish that the primary rearrangement pathway for 1a involves ketene formation in accordance with the photo-Wolff rearrangement. Furthermore we have also demonstrated the synthetic utility of 1a as an esterification and etherification reagent with a variety of substituted α-diazo-p- hydroxyacetophenones, using them as synthons for efficiently coupling it to acids and phenols to produce pHP protect substrates. The Royal Society of Chemistry and Owner Societies.

P-Hydroxyphenacyl photoremovable protecting groups Robust photochemistry despite substituent diversity

A broadly based investigation of the effects of a diverse array of substituents on the photochemical rearrangement of p-hydroxyphenacyl esters has demonstrated that common substituents such as F, MeO, CN, CO2R, CONH2, and CH3 have little effect on the rate and quantum efficiencies for the photo-Favorskii rearrangement and the release of the acid leaving group or on the lifetimes of the reactive triplet state. A decrease in the quantum yields across all substituents was observed for the release and rearrangement when the photolyses were carried out in buffered aqueous media at pHs that exceeded the ground-state pKa of the chromophore where the conjugate base is the predominant form. Otherwise, substituents have only a very modest effect on the photoreaction of these robust chromophores.