40180-70-9

Usage

Preparation

Preparation from 5-acetyl-4-methyl-3-cyclohexenone by aromatization promoted, ? by cupric bromide with lithium bromide in refluxing acetonitrile (80%) ; ? by 10% Pd/C in refluxing xylene (50%).

InChI:InChI=1/C9H10O2/c1-6-3-4-8(11)5-9(6)7(2)10/h3-5,11H,1-2H3

Upstream product

• 578-22-3 2-methyl-5-hydroxybenzoic acid 
• 917-54-4 methyllithium 
• 534-22-5 2-methylfuran 
• 1423-60-5 methyl ethynyl ketone 
• 140-39-6 1-acetoxy-4-methylbenzene 
• 106-44-5 p-cresol 
• 1202-08-0 2-methyl-5-isopropylacetophenone 
• 40180-68-5 1-[5-(1-Hydroperoxy-1-methyl-ethyl)-2-methyl-phenyl]-ethanone 
• 145300-01-2 5-acetyl-4-methyl-3-cyclohexenone 

Downstream Products

• 1192215-70-5 2-bromo-1-(5-hydroxy-2-methylphenyl)ethanone 

Relevant academic research and scientific papers

Substrate substitution effects in the Fries rearrangement of aryl esters over zeolite catalysts

The catalytic transformation of aryl esters to hydroxyacetophenones via Fries rearrangement over solid acids is of interest to avoid the use of corrosive and toxic Lewis and Br?nsted acids traditionally applied. Microporous zeolites are known to catalyze the reaction of simple substrates such as phenyl acetate, but their application to substituted derivatives has received limited attention. To refine structure-activity relationships, here we examine the impact of various parameters including the solvent polarity, water content, acidic properties, and framework type on the reaction scheme in the Fries rearrangement of p-tolyl acetate over common solid acids. The results confirm the importance of providing a high concentration of accessible Br?nsted acid sites, with beta zeolites exhibiting the best performance. Extension of the substrate scope by substituting methyl groups in multiple positions identifies a framework-dependent effect on the rearrangement chemistry and highlights the potential for the transformation of dimethylphenyl acetates. Kinetic studies show that the major competitive path of cleavage of the ester C-O bond usually occurs in parallel to the Fries rearrangement. The possibility of sequentially acylating the resulting phenol depends on the substrate and reaction conditions.

METHOD TO PREPARE PHENOLICS FROM BIOMASS

The present invention is directed to a method for preparing a final phenolic product from biomass comprising the steps of providing a furanic compound obtainable from biomass; reacting the furanic compound with a dienophile to obtain a phenolic compound; reacting the phenolic compound further to obtain the final phenolic product.

Structure-based optimization of potent and selective inhibitors of the tyrosine kinase erythropoietin producing human hepatocellular carcinoma receptor B4 (EphB4)

The tyrosine kinase EphB4 is an attractive target for drug design because of its recognized role in cancer-related angiogenesis. Recently, a series of commercially available xanthine derivatives were identified as micromolar inhibitors of EphB4 by high-throughput fragment-based docking into the ATP-binding site of the kinase domain. Here, we have exploited the binding mode obtained by automatic docking for the optimization of these EphB4 inhibitors by chemical synthesis. Addition of only two heavy atoms, methyl and hydroxyl groups, to compound 4 has yielded the single-digit nanomolar inhibitor 66, with a remarkable improvement of the ligand efficiency from 0.26 to 0.37 kcal/(mol per non-hydrogen atom). Compound 66 shows very high affinity for a few other tyrosine kinases with threonine as gatekeeper residue (Abl, Lck, and Src). On the other hand, it is selective against kinases with a larger gatekeeper. A 45 ns molecular dynamics (MD) simulation of the complex of EphB4 and compound 66 provides further validation of the binding mode obtained by fragment-based docking. 2009 American Chemical Society.