19447-06-4

Upstream product

• 608-28-6 2,6-dimethyliodobenzene 
• 2142-76-9 2',6'-dimethylacetophenone 
• 75-07-0 acetaldehyde 
• 21450-64-6 (2,6-dimethylphenyl)magnesium bromide 
• 917-64-6 methyl magnesium iodide 
• 1123-56-4 2,6-dimethylbenzaldehyde 
• 576-22-7 2-Bromo-m-xylene 
• 87-62-7 2,6-dimethylaniline 
• 75-21-8 oxirane 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 55968-40-6 1-chloro-1-(2,6-dimethylphenyl)ethane 
• 19447-08-6 α,2,6-Trimethyl-3-brom-benzylalkohol 
• 25140-35-6 meso-2,3-Bis-(2,6-dimethyl-phenyl)-butan 
• 25140-35-6 C₂₀H₂₆ 
• 719304-89-9 (S)-1-(2,6-dimethylphenyl)ethan-1-ol 
• 719304-89-9 (R)-1-(2,6-dimethylphenyl)ethanol 
• 190374-00-6 2-(1,2-dibromoethyl)-1,3-dimethylbenzene 
• 292820-32-7 1-(2,6-dimethylphenyl)ethyl bromide 
• 719304-89-9 (+)-1-(2,6-dimethylphenyl)ethanol 
• 459451-20-8 5-(2-Piperidinyl-ethyl)-2-methyl-1H-indole-3-carboxylic 1-(2,6-dimethylphenyl)-ethyl ester 
• 2142-76-9 2',6'-dimethylacetophenone 
• 2039-90-9 2,6-dimethylstyrene 

Relevant academic research and scientific papers

Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts

A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.

Selective C-alkylation Between Alcohols Catalyzed by N-Heterocyclic Carbene Molybdenum

The first implementation of a molybdenum complex with an easily accessible bis-N-heterocyclic carbene ligand to catalyze β-alkylation of secondary alcohols via borrowing-hydrogen (BH) strategy using alcohols as alkylating agents is reported. Remarkably high activity, excellent selectivity, and broad substrate scope compatibility with advantages of catalyst usage low to 0.5 mol%, a catalytic amount of NaOH as the base, and H2O as the by-product are demonstrated in this green and step-economical protocol. Mechanistic studies indicate a plausible outer-sphere mechanism in which the alcohol dehydrogenation is the rate-determining step.

Catalytic hydrogenation of carbonyl and nitro compounds using an [: N, O] -chelate half-sandwich ruthenium catalyst

A series of N,O-chelate half-sandwich ruthenium complexes for both carbonyl and nitro compound hydrogenation have been synthesized based on β-ketoamino ligands. All complexes exhibited high activity for the catalytic hydrogenation of a series of ketones and nitroarenes with molecular H2 as the reducing reagent in aqueous medium. Consequently, the catalytic system showed the catalytic TON values of 950 for 1-phenylethanol in acetophenone hydrogenation and 1960 for 1-chloro-4-nitrobenzene in p-chloroaniline hydrogenation. Good catalytic activity was displayed for various kinds of substrates with either electron-donating or electron-withdrawing groups. The neutral ruthenium complexes 1-4 were fully characterized using NMR, IR, and elemental analysis. Molecular structures of complexes 2 and 4 were further confirmed using single-crystal X-ray diffraction analysis.

Half-sandwich ruthenium-based versatile catalyst for both alcohol oxidation and catalytic hydrogenation of carbonyl compounds in aqueous media

A series of half-sandwich ruthenium-based catalysts for both alcohol oxidation and carbonyl compounds hydrogenation have been synthesized through metal-induced C–H bond activation based on benzothiazole ligands. The neutral ruthenium complexes 1–4 were fully characterized by UV–vis, NMR, IR, and elemental analysis. Molecular structures of complexes 1 and 3 were further confirmed by X-ray diffraction analysis. All complexes exhibited high activity for the catalytic oxidation of a variety of alcohols with tBuOOH as oxidants to give carbonyl compounds with high yields in water. Moreover, these half-sandwich complexes also showed high efficiency for the catalytic hydrogenation of carbonyl compounds in a methanol–water mixture. The catalyst could be reused for at least five cycles without any loss of activity. The catalytic system also worked well for various kinds of substrates with either electron-donating or electron-withdrawing groups.

PROCESS FOR PREPARING SUBSTITUTED 2-ARYLETHANOLS

The invention relates to a process for preparing substituted 2-arylethanols of the formula (I) by reacting Grignard compounds of the formula (II) in the presence of a copper compound with ethylene oxide. Moreover, the invention relates to novel substituted 2-arylethanols of the formula (I).

Optimization of inhibitors of the tyrosine kinase EphB4. 2. Cellular potency improvement and binding mode validation by X-ray crystallography

Inhibition of the tyrosine kinase erythropoietin-producing human hepatocellular carcinoma receptor B4 (EphB4) is an effective strategy for the treatment of solid tumors. We have previously reported a low nanomolar ATP-competitive inhibitor of EphB4 discovered in silico by fragment-based high-throughput docking combined with explicit solvent molecular dynamics simulations. Here we present a second generation of EphB4 inhibitors that show high inhibitory potency in both enzymatic and cell-based assays while preserving the appealing selectivity profile exhibited by the parent compound. In addition, respectable levels of antiproliferative activity for these compounds have been obtained. Finally, the binding mode predicted by docking and molecular dynamics simulations is validated by solving the crystal structures of three members of this chemical class in complex with the EphA3 tyrosine kinase whose ATP-binding site is essentially identical to that of EphB4.

Metal triflate-catalyzed cationic benzylation and allylation of 1,3-dicarbonyl compounds

(Chemical Equation Presented) The rare earth metal and hafnium triflate-catalyzed secondary benzylation and allylation of 1,3-diketones, ketoesters, and ketoamides are described. The procedure was carried out under non-anhydrous conditions. Various 1-phenylethyl cations were generated from substituted 1-phenylethanols using 0.5 mol % of the metal triflates in CH 3NO2. The cations reacted with 1,3-diketones and ketoesters to give benzylated products in high yields. Following the GC analysis, the reaction conditions were easily optimized by the selection of catalysts based on the Lewis acidity of the triflates and reaction temperature. A tertiary-alkylated diketone and a corresponding ketoester were also benzylated to afford products with a quaternary carbon atom in 57-84% yield. The ketoamide reactions required stronger Lewis acids than those used in the diketone and ketoester reactions. The reactions of benzylic alcohols possessing various substituents on the aromatic ring and dibenzoylmethane (2b) as a diketone were examined in the presence of Hf(OTf)4. Electron-rich benzylic alcohols reacted with 2b in 86-96% yield, and electron-deficient alcohol gave the desired product in 79-65% yield. Despite possessing a strong electron-withdrawing group, the reaction of 1-(4-nitrophenyl)ethanol gave the corresponding product in 61% yield. It was also possible to use allylic alcohols directly for the allylation of diketone 2b. The catalyst can be recovered by water extraction and reused up to five times.

Relationship between the structure and enantioselectivity in the asymmetric reduction of 2′,6′-disubstituted acetophenones with DIP-Chloride. An ab initio study

Using computational and chemical studies, a relationship between the % ee achieved and the dihedral angles between the plane of the aromatic ring and the plane containing the carbonyl group has been established for asymmetric reductions with B-chlorodiisopinocampheylborane.

Axially chiral analogues of 4-(dimethylamino)pyridine: Novel catalysts for nonenzymatic enantioselective acylations

A concise seven-step synthesis of atropisomeric 3-aryl analogues of DMAP from 4-pyridone 8 has been developed. A representative compound of this class, biaryl (±)-15, has been resolved using CSP HPLC and shown to be an efficient nucleophilic catalyst for kinetic resolution of a series of secondary alcohols on both an analytical and preparative scale (stereoselectivity factors, s = 8.9-29).