32123-84-5

Usage

Uses

Used in the Fragrance Industry:
Methyl(α-methylenebenzyl) ketone is used as an odorant for masking, scenting, and odorization of various products, particularly in the fragrance industry. Its aromatic properties make it suitable for enhancing the smell of different items, providing a pleasant and lasting scent.
Used in the Petroleum Industry:
Methyl(α-methylenebenzyl) ketone is also utilized in the petroleum industry as an additive for hydrocarbon oils, fuels, and petroleum products. It serves to improve the odor profile of these products, making them more acceptable to consumers and ensuring a better overall experience during use.

InChI:InChI=1/C10H10O/c1-8(9(2)11)10-6-4-3-5-7-10/h3-7H,1H2,2H3

Upstream product

• 51-80-9 bis-(dimethylamino)methane 
• 43108-63-0 1-phenyl-2-trimethylsiloxy-1-propene 
• 35307-29-0 3-bromo-3-phenylbutan-2-one 
• 50366-70-6 3-phenyl-4-tosyl-2-butanone 
• 18476-73-8 (3-methylbuta-1,3-dien-2-yl)benzene 
• 107454-91-1 1-nitro-2-phenyl-2,3-epoxybutane 
• 873-55-2 sodium benzenesulfonate 
• 119044-24-5 (E)-2-phenyl-3-phenylthio-but-2-ene-1-ol 
• 119044-25-6 Z-2-phenyl-3-phenylthiobut-2-ene-1-ol 
• 103-79-7 1-phenyl-acetone 
• 30354-18-8 N,N-dimethyl(methylene)ammonium chloride 
• 50-00-0 formaldehyd 
• 119044-12-1 (E)-2-phenyl-3-phenylthio-but-2-enal 
• 119044-21-2 (Z)-2-phenyl-3-phenylthio-but-2-enal 

Downstream Products

• 114646-77-4 1-(6-methyl-2,5-diphenyl-3,4-dihydro-2H-pyran-2-yl)ethanone 
• 769-59-5 3-phenyl-butan-2-one 
• 740035-36-3 1-(2-methyl-5-phenyl-isoxazolidin-5-yl)-ethanone 
• 93-58-3 benzoic acid methyl ester 
• 109-87-5 Dimethoxymethane 
• 107-31-3 Methyl formate 
• 79-20-9 acetic acid methyl ester 
• 4461-52-3 methoxymethanol 
• 65-85-0 benzoic acid 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 10027-72-2 methoxymethyl hydroperoxide 
• 107729-24-8 1-Hydroperoxy-1-methoxy-1-phenyl-propan-2-one 
• 116375-60-1 4-(tert-Butyl-hydroxy-amino)-3-phenyl-butan-2-one 
• 75232-78-9 3-phenyl-5,6,7,8-tetrahydronaphthalen-2-ol 

Relevant academic research and scientific papers

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.

Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination

A formal enone α-arylation is described. This metal-free transformation relies on the I(III)-mediated skeletal reorganization of silyl enol ethers and features mild conditions, good yields, and high stereoselectivities for β-substituted enones.

METHOD FOR PREPARING CHLORINATED KETONE COMPOUNDS

PROBLEM TO BE SOLVED: To provide a method for efficiently producing a α-methylene ketone compound, which is widely found in natural products and is known as a biologically active substance, by a method in which an α, α-disubstituted allyl alcohol compound is used as a raw material, and an expensive oxidizing agent such as a heavy metal system is not used and an environmental load is reduced. SOLUTION: An α, α-disubstituted allyl alcohol compound represented by general formula (1) (wherein R1 and R2 each represents an alkyl group, an aromatic hydrocarbon group, or an alicyclic hydrocarbon group; alternatively, R1 and R2 may form together an aliphatic hydrocarbon ring), is oxidized in the presence of tetraalkylammonium hypochlorite to give a chlorinated ketone compound. This chlorinated ketone compound can be made into an α-methylene ketone compound by dehydrochlorination in the presence of a base. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Bromomethyl Silicate: A Robust Methylene Transfer Reagent for Radical-Polar Crossover Cyclopropanation of Alkenes

A general protocol for visible-light-induced cyclopropanation of alkenes was developed with bromomethyl silicate as a methylene transfer reagent, offering a robust tool for accessing highly valuable cyclopropanes. In addition to α-aryl or methyl-substituted Michael acceptors and styrene derivatives, the unactivated 1,1-dialkyl ethylenes were also shown to be viable substrates. Apart from realizing the cyclopropanation of terminal alkenes, the methyl transfer reaction has been further demonstrated to be amenable to the internal olefins. The photocatalytic cyclopropanation of 1,3-bis(1-arylethenyl)benzenes was also achieved, giving polycyclopropane derivatives in excellent yields. With late-stage cyclopropanation as the key strategy, the synthetic utility of this transformation was also demonstrated by the total synthesis of LG100268.

Enantioselective Bromolactonization of Trisubstituted Olefinic Acids Catalyzed by Chiral Pyridyl Phosphoramides

Enantioselective bromolactonization of trisubstituted olefinic acids producing synthetically useful chiral lactones with two contiguous asymmetric centers has remained mainly unexplored except for the 6-exo cyclization mode. In this work, the 5-exo- and 6

Enantioselective synthesis of β-substituted chiral allylic amines: Via Rh-catalyzed asymmetric hydrogenation

An asymmetric mono-hydrogenation of 2-acetamido-1,3-dienes catalyzed by a Rh-DuanPhos complex has been developed. This approach provides easy access to chiral allylic amines with excellent enantioselectivities and high regioselectivities. The products are valuable chiral building blocks for pharmaceuticals.

Ene di- and trimerization of 1-methyl-2-phenylcyclopropene

1,2-Disubstituted cyclopropene, 1-methyl-2-phenylcyclopropene (18), was generated by bromo-lithium exchange of 1-bromo-2-phenylcyclopropene followed by treatment with methyl iodide. Compound 18 was oxidized by oxygen to give the α,β-unsaturated carbonyl product 25 and diketone 27 and the tautomeric, β-hydroxyl-α,β-unsaturated ketone 28. However, compound 28 reacted further with the cyclopropene 18 in a retro-Claisen-like reaction to generate adduct 26. Furthermore, compound 18 underwent ene dimerization in neat condition to form the endo-dimer 40 and exo-dimer 41 followed by oxidization with oxygen to give aldehyde 39. It is noteworthy that the endo-dimer 40 and exo-dimer 41 could be trapped with thiophenol to give adduct 42 and 43. In addition, the ene reaction of exo-dimer 41 with monomer 18 gave an exo-exo ene trimer 46 through an exo-transition state which was also trapped by thiophenol to give adducts 44 and 45.

Metal-free, one-pot, sequential protocol for transforming ,-epoxy ketones to -hydroxy ketones and -methylene ketones

A new sequential, one-pot protocol for transforming 1,3-disubstituted 2,3-epoxy ketones to β;-hydroxy ketones and α-methylene ketones has been developed. Reaction of epoxy ketones with boron trifluoride etherate (BF3·OEt2) generates the cationic intermediates by regioselective epoxide ring opening and an acyl shift. Then, a treatment of these cations with 2-aryl-1,3-dimethylbenzimidazolines (DMBIH) results in formation of 1,2-disubstituted 3-hydroxy ketones. DMBIH serves as a hydride donor in the second step of this process. Finally, the β;-hydroxy ketones can be converted to 1,2-disubstituted 2-methylene ketones by treatment with methanesulfonic acid or a combination of methanesulfonyl chloride and triethylamine. Importantly, the sequential steps involved in formation of the α-methylene ketone products can be carried out in one pot.

Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation

α,β-Unsaturated oxime pivalates are proposed to undergo reversible C(sp2)-H insertion with cationic Rh(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to convert these molecules into piperidines, which are important structural components of numerous pharmaceuticals.

Nonenzymatic kinetic resolution of α-aryl substituted allylic alcohols catalyzed by acyl transfer catalyst Np-PIQ

Chiral α-aryl substituted allylic alcohols are important versatile synthetic intermediates. We report here an effective nonenzymatic kinetic resolution of racemic α-aryl substituted allylic alcohols by introducing different aryl groups with acyl transfer