5650-07-7

Usage

InChI:InChI=1/C11H12O/c1-9(2)8-11(12)10-6-4-3-5-7-10/h3-8H,1-2H3

Upstream product

• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 2674-04-6 diphenyl cadmium 
• 71-43-2 benzene 
• 1871-57-4 2-chloromethyl-3-chloroprop-1-ene 
• 98-88-4 benzoyl chloride 
• 29917-94-0 2-methylprop-1-enyllithium 
• 917-64-6 methyl magnesium iodide 
• 185245-65-2 3-methylthio-3-N-piperidino-1-phenyl-2-propen-1-one 
• 20846-00-8 2-nitro-propan-2-ide 
• 28531-58-0 (2-oxo-2-phenylethyl)mercury chloride 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 563-47-3 3-Chloro-2-methylpropene 
• 78-84-2 isobutyraldehyde 
• 98-86-2 acetophenone 

Downstream Products

• 105337-08-4 4-methyl-2-phenylpent-3-en-2-ol 
• 69096-81-7 3-methyl-1,3-ddiphenylbutan-1-one 
• 39533-27-2 4-methyl-6-phenyl-[1,2]oxathiin-2,2-dioxide 
• 582-62-7 3-methyl-1-phenylbutan-1-one 
• 64097-38-7 2,3-dibromo-3-methyl-1-phenylbutan-1-one 
• 38010-47-8 (E)-3-Hydroxy-2,2,3-trimethyl-5-phenyl-pent-4-enenitrile 
• 58006-78-3 4,7-dihydro-7,7-dimethyl-5-phenyl-1,2,4-oxadiazepin-3(2H)-one 
• 50299-81-5 trans-(2,2-dimethyl-3-phenylcyclopropyl)-phenylmethanone 
• 133817-07-9 2,2,3,3-Tetramethyl-5-oxo-5-phenyl-pentanoic acid ethyl ester 
• 89881-67-4 3-dimethyl(phenyl)silyl-3-methyl-1-phenylbutane 
• 96633-35-1 1-p-tolyl-2,3,3-trimethyl-5-phenyl-1,5-pentanedione 
• 64097-37-6 2-Benzoyl-3,7-dimethyl-aziridin 
• 75115-09-2 3-methyl-1-phenyl-2-buten-1-one (E)-oxime 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Diastereo- and Enantioselective Formal [3 + 2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay

We report a stereoselective formal [3 + 2] cycloaddition of cyclopropyl ketones and radical-acceptor alkenes to form polysubstituted cyclopentane derivatives. Catalyzed by a chiral Ti(salen) complex, the cycloaddition occurs via a radical redox-relay mechanism and constructs two C-C bonds and two contiguous stereogenic centers with generally excellent diastereo- and enantioselectivity.

Dimerization of cyclopropyl ketones and crossed reactions of cyclopropyl ketones with enones as an entry to five-membered rings

An unexpected dimerization of cyclopropyl ketones was observed, and analysis of the reaction pathway led to development of a synthetically useful crossed reaction between cyclopropyl ketones and enones to afford densely functionalized cyclopentane product

Alcohol Dehydrogenases and N-Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β-Disubstituted Allylic Alcohols

The combination of gold(I) and enzyme catalysis is used in a two-step approach, including Meyer–Schuster rearrangement of a series of readily available propargylic alcohols followed by stereoselective bioreduction of the corresponding allylic ketone intermediates, to provide optically pure β,β-disubstituted allylic alcohols. This cascade involves a gold N-heterocyclic carbene and an enzyme, demonstrating the compatibility of both catalyst types in aqueous medium under mild reaction conditions. The combination of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2) and a selective alcohol dehydrogenase (ADH-A from Rhodococcus ruber, KRED-P1-A12 or KRED-P3-G09) led to the synthesis of a series of optically active (E)-4-arylpent-3-en-2-ols in good yields (65–86 %). The approach was also extended to various 2-hetarylpent-3-yn-2-ol, hexynol, and butynol derivatives. The use of alcohol dehydrogenases of opposite selectivity led to the production of both allyl alcohol enantiomers (93->99 % ee) for a broad panel of substrates.

Visible Light Mediated Photocatalytic N-Radical Cascade Reactivity of O,δ-Unsaturated N-Arylsulfonylhydrazones: A General Approach to Structurally Diverse Tetrahydropyridazines

Tetrahydropyridazines are of particular interest for their versatility as intermediates in organic synthesis and display pharmacological activity in several domains. Here, we describe the photocatalytic synthesis of different tetrahydropyridazines starting from O,δ-unsaturated N-arylsulfonylhydrazones. Simple structural changes of substrates result into three different pathways beginning from a common N-hydrazonyl radical, which evolves through a domino carboamination/dearomatization, a HAT process, or a photoinduced radical Smiles rearrangement to afford diverse tetrahydropyridazines. All reactions are carried out in very mild conditions, and the quite inexpensive [Ru(bpy)3]Cl2 is used as the catalyst. Preliminary mechanism studies are presented, among them luminescence and electrochemical characterization of the involved species. Computational studies allow to rationalize the mechanism in accord with the experimental findings.

Pd-catalyzed imine-directed intramolecular C–N bond formation through C(sp3)–H activation: An efficient approach to multisubstituted pyrroles

An atom-economic approach to synthesize 1,2,4-trisubstituted pyrroles through palladium-catalyzed imine-directed intramolecular C(sp3)–H amination reaction has been developed. The imine group acts as a directing group as well as an intramolecular nucleophile for the first time in intramolecular C–N bonds formation reactions.

Nickel-Catalyzed Chemoselective Asymmetric Hydrogenation of α,β -Unsaturated Ketoimines: An Efficient Approach to Chiral Allylic Amines

An efficient synthetic route to chiral allylic amines has been developed by nickel/(S,S)-Ph-BPE complex catalyzed chemoselective asymmetric hydrogenation of α,β-unsaturated ketoimines. Varieties of α,β-unsaturated ketoimines have been well tolerated in this transformation to give chiral allylic amines with high yields and excellent ee values (up to 99% yield, up to 99% ee). A gram-scale reaction with 0.2 mol % catalyst loading has also been achieved.

Palladium-Catalyzed Hydrocarbonylative Cyclization of 1,5-Dienes

A novel and atom-economic palladium-catalyzed isomerization-hydrocarbonylative cyclization reaction of 1,5-dienes to 2-alkylidenecyclopentanones has been developed, which provides a rapid and straightforward approach to 2-alkylidenecyclopentanones with high stereoselectivity. The reaction was found to proceed via alkene isomerization and selective hydrocarbonylative cyclization to generate 2-alkylidenecyclopentanones with high selectivity.

Synthesis of Enones and Enals via Dehydrogenation of Saturated Ketones and Aldehydes

A general, efficient and economic palladium-catalyzed dehydrogenation to form enones or enals has been developed. The approach possesses extremely broad substrate scope including various linear or cyclic saturated ketones and aldehydes. The protocol is ligand-free, and molecular oxygen is used as the sole clean oxidant in the reaction. Due to mild reaction conditions, good functional group compatibility, and versatile utilities of enones and enals, the method can be applied in the late-stage synthesis of natural products, pharmaceuticals and fine chemicals. (Figure presented.).

A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis

A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. In contrast to other more common methods for [3+2] cycloaddition, these conditions o

Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones

Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.