73252-30-9

Upstream product

• 2528-61-2 Heptanoic acid chloride 
• 108-88-3 toluene 
• 67132-63-2 Se-methyl heptaneselenoate 
• 111098-80-7 bis(benzotriazolo)(4-methylphenyl)methane 
• 258864-54-9 trihexyl(tetradecyl)phosphonium chloride 
• 17264-54-9 sodium p-methylbenzoate 
• 111-14-8 oenanthic acid 
• 328-51-8 2-oxooctanoic acid 
• 624-31-7 4-tolyl iodide 
• 874-60-2 4-methyl-benzoyl chloride 
• 614-54-0 1-phenylheptan-1-ol 
• 71434-32-7 1-(p-tolyl)heptan-1-ol 
• 111-25-1 1-bromo-hexane 
• 592-41-6 1-hexene 

Downstream Products

• 92330-55-7 p-Methyl-α-hexyl-benzylamin 
• 92377-94-1 2-methyl-1-(4-methylphenyl)cyclohexene 

Relevant academic research and scientific papers

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids

The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate scope is observed with respect to both the oxo acid and arene coupling partners. This mild decarboxylative arylation can also be utilized to efficiently access medicinal agents, as demonstrated by the rapid synthesis of fenofibrate. The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate scope is observed with respect to both the oxo acid and arene coupling partners.

Chemoselective oxidation by electronically tuned nitroxyl radical catalysts

Electronic tuning: Nitroxyl radical 1 is shown to be an efficient catalyst for the oxidation of secondary alcohols, and promotes oxidation through an oxoammonium species which is highly reactive because of the adjacent electron-withdrawing ester groups. Chemoselective oxidation of benzylic alcohols in the presence of aliphatic alcohols is observed and is proposed to proceed by a rate-determining hydride transfer. Copyright

Friedel-crafts acylation of arenes with carboxylic acids using polystyrene-supported aluminum triflate

Cross-linked polystyrene-supported aluminum triflate (Ps-Al(OTf) 3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for the acylation of aromatic compounds. The catalyst can be easily prepared from cheap starting materials, is stable (as a bench top catalyst) and is reusable.

Friedel-Crafts acylation of arenes with carboxylic acids using silica gel supported AlCl3

Aromatic compounds react smoothly with carboxylic acids in the presence of silica gel supported aluminium trichloride to afford the corresponding ketones with high regioselectivity in high to excellent yields. The catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency. tuebitak.

Reactivity of trihexyl(tetradecyl)phosphonium chloride, a room-temperature phosphonium ionic liquid

Trihexyl(tetradecyl)phosphonium chloride 1, a room-temperature ionic liquid, readily undergoes deuterium isotope exchange reaction in deuterated solvents. Under basic conditions, ionic liquid 1 was reactive and 50% deuterium exchanged on all four P-CH2 methylene groups in 9 h at ambient temperature, 30 min at 50 °C, or 12 min at 65 °C. In addition, ionic liquid 1 reacted with sodium salts of substituted benzoates apparently through the direct SN2 carboxylate alkylation to form esters 2 and the resulting esters further converted, via Wittig reaction, to finally afford aryl ketones 4.

NOVEL METHODS FOR THE TREATMENT OF INFLAMMATORY DISEASES

Methods of inhibiting the cytokine or biological activity of Macrophage Migration Inhibitory Factor (MIF) comprising contacting MIF with a compound of formula (I) are provided. The invention also relates to methods of treating diseases or conditions where MIF cytokine or biological activity is implicated comprising administration of compounds of formula (I), either alone or as a part of combination therapy. Novel compounds of formula (I) are also provided for.

Direct conversion of benzyl alcohol to ketone by polymer-supported Rh catalyst

Benzyl alcohol reacted with 1-alkene to give the corresponding ketone by in situ generated polystyrene-based rhodium catalyst. The catalytic activity of this polymer-supported rhodium catalyst has not been reduced after reusing it four times.

The Chemistry of N-Substituted Benzotriazoles. Part 6. A New Synthetic Route to Aromatic Ketones

Lithiation of p-bis(benzotriazol-1-yl)methyltoluene (4) gives the carbanion (5) which affords substitution products with many electrophiles.Acidic hydrolysis of the lithiation products affords the corresponding aromatic ketones in good yield.The syntheses of simple ketones, of diketones, and of α-hydroxy ketones are described.

DIMETHYLALUMINIUM METHANESELENOLATE - A USEFUL REAGENT FOR THE PREPARATION OF SELENOESTERS. A NEW FRIEDEL-CRAFTS ACYLATION PROCEDURE PROMOTED BY Cu(I)

The preparation of a new aluminium reagent, dimethylaluminium methaneselenolate (Me2AlSeMe) is described.The reactivity of this aluminium reagent toward a variety of organic substrates has been studied.Me2AlSeMe will convert O-alkyl esters to selenoesters in high yield.These selenoesters function as extremely reactive acyl transfer agents and are converted to acids, esters, and amides on reaction with water, alcohols or amines in the presence of a selenophilic metal cation.The selenoesters will, moreover, acylate reactive arenes and heterocyclic compounds when cuprous triflate is employed as the selenophilic metal cation.This latter transformation constitutes a new transition metal promoted variant of the Friedel-Crafts acylation reaction.