25870-62-6

Usage

Synthesis Reference(s)

Tetrahedron Letters, 7, p. 5669, 1966 DOI: 10.1016/0005-2760(66)90119-6

InChI:InChI=1/C12H16O/c1-2-3-9-12(13)10-11-7-5-4-6-8-11/h4-8H,2-3,9-10H2,1H3

Upstream product

• 141765-79-9 α-Pentanoyl-α-phenyl-acetonitril 
• 110-59-8 pentanonitrile 
• 6921-34-2 benzylmagnesium chloride 
• 103-82-2 phenylacetic acid 
• 109-52-4 valeric acid 
• 2726-81-0 benzyltri-n-butylphosphonium iodide 
• 22535-03-1 phenylacetyl bromide 
• 1119-90-0 di-n-butylzinc 
• 3431-67-2 di-n-butylcadmium 
• 56651-44-6 1,1-bis-phenylsulfanyl-pentane 
• 1694-84-4 tribenzylborane 
• 2168-93-6 butyl sulfoxide 
• 101-97-3 Ethyl 2-phenylethanoate 
• 693-03-8 n-butyl magnesium bromide 

Downstream Products

• 41718-52-9 4-phenylnonan-5-one 
• 626-97-1 pentamide 
• 77989-13-0 3-n-butyl-4-phenyl-1,2,5-thiadiazole 
• 84735-50-2 1,2-diphenyl-2-hexanol 
• 641144-58-3 2-benzyl-2-trimethylsilanyloxy-hexanenitrile 
• 641144-59-4 2-benzyl-2-hydroxyhexanenitrile 

Relevant academic research and scientific papers

Spectroscopic identification of the nickel acylate complex

NMR and IR spectral data of the pentanoyl nickelate complex are presented and are consistent with a mononuclear nickel complex. This nickel acylate complex is thermally stable in THF at ambient temperature (+20°C) for prolonged periods (24 h) but decomposes rapidly in air.

Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents

An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.

Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides

Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.

C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis

Catalyst controlled site-selective C-H functionalization is a challenging but powerful tool in organic synthesis. Polarity-matched and sterically controlled hydrogen atom transfer (HAT) provides an excellent opportunity for site-selective functionalization. As such, the dual Ni/photoredox system was successfully employed to generate acyl radicals from aldehydes via selective formyl C-H activation and subsequently cross-coupled to generate ketones, a ubiquitous structural motif present in the vast majority of natural and bioactive molecules. However, only a handful of examples that are constrained to the use of aryl halides are developed. Given the wide availability of amines, we developed a cross-coupling reaction via C-N bond cleavage using the economic nickel and TBADT catalyst for the first time. A range of alkyl and aryl aldehydes were cross-coupled with benzylic and allylic pyridinium salts to afford ketones with a broad spectrum of functional group tolerance. High regioselectivity toward formyl C-H bonds even in the presence of α-methylene carbonyl or α-amino/oxy methylene was obtained.

A simple synthesis of ketone from carboxylic acid using tosyl chloride as an activator

An effective process for the conversion of carboxylic acid to ketone has been discovered. In this process, carboxylic acid has been activated using p-toluene sulphonyl group. Under the optimized condition, aromatic, aliphatic heteroaromatic carboxylic acids have been proved to be good substrates for this methodology. The byproduct of this reaction can be removed very easily during work up process. Also, one equivalent of organometallic reagent is sufficient to complete this transformation.

Simple one pot synthesis of ketone from carboxylic acid using DCC as an activator

Simple one pot procedure for the conversion of carboxylic acid to ketone is described. Various carboxylic acids were converted to the corresponding ketones in excellent manner in presence of N,N′-dicyclohexylcarbodiimide (DCC) and organometallic reagents. Aromatic, heteroaromatic and aliphatic acids were converted to the corresponding ketones smoothly under the optimum conditions using organolithium reagents. In this process, desired products have been isolated from the crude reaction mixtures in moderate yields during the purification process.

Rational Design of a Metallocatalytic Cavitand for Regioselective Hydration of Specific Alkynes

The synthesis of a functionalized supramolecular cavitand with inwardly oriented AuI and P=O moieties was explored, including its catalytic proclivity in the selective hydration of internal alkynes. The cavitand works as a supramolecular flask device: AuI coordinates to the triple bond, the P=O moiety connects with a H2O molecule, and the cavity favors folding of a single alkynyl side chain. Several tests of different substrate patterns indicated that the cavity was substrate specific, similar to enzymatic catalysis.

Synthesizing method of alpha-arone or alpha-hetero-arone

The invention discloses a synthesizing method of alpha-arone or alpha-hetero-arone and belongs to the technical field of metal organic catalyzing. The synthesizing method has the advantages that a terminal alkynyl compound, oxynitride and a proton supply agent is catalyzed by univalence metal salt to obtain N-O pyridine oxynitride enol salt, purification and separation are not needed, and the N-Opyridine oxynitride enol salt is allowed to have reaction with arene and hetero-arene in a one-pot manner to obtain the alpha-arone or alpha-hetero-arone; the method is high in functional group tolerance, wide in substrate application range, high in yield, simple and easy to operate and easy in final product separation and purification.

Regioselective Arene and Heteroarene Functionalization: N-Alkenoxypyridinium Salts as Electrophilic Alkylating Agents for the Synthesis of α-Aryl/α-Heteroaryl Ketones

A direct regioselective functionalization of arenes and heteroarenes using N-alkenoxypyridinium salts as electrophilic alkylating agents for the synthesis of α-aryl/heteroaryl ketones has been developed. The method generates alkylating agents from alkynes and N-pyridine oxide followed by site-selective electrophilic substitution with a broad range of arenes and heteroarenes including benzene derivates, phenols, ethers, indoles, pyrroles, furans, and thiophenes in one pot. Kinetic isotope effect measurements and DFT studies reveal that this reaction likely proceeds through a carbon-cation intermediate.

Internal Alkyne Regio- and Chemoselectivity using a Zwitterionic N-Heterocyclic Carbene Gold Catalyst in a Silver-Free Alkyne Hydration Reaction

An alkyne hydration of terminal and internal alkynes is reported using a zwitterionic N-heterocyclic carbene gold catalyst [(BNHC)Au(SMe2)] in the absence of silver and Br?nsted acid additives. The hydration demonstrates good regioselectivity in alkyne hydration and chemoselectivity for internal alkynes vs. terminal. In addition, (BNHC)Au(SMe2) performs a propargyl alcohol hydration to predominantly form α-hydroxymethyl ketone over the more common Meyer–Schuster rearrangement product. While complex (BNHC)Au(SMe2) is active without silver additives, addition of silver hexafluoroantimonate (AgSbF6) increases reaction rate and decreases selectivity for internal alkyne hydration over terminal substrates. To the best of our knowledge, the rate enhancement of (BNHC)Au(SMe2) by AgSbF6is the first such demonstration of a silver effect for a “halide-free” Au catalyst. (Figure presented.).