40463-09-0

Basic information

• Product Name: 4-methyl-1-phenylpentan-3-one
• Synonyms: 4-methyl-1-phenylpentan-3-one;1-Phenyl-4-methyl-3-pentanone;2-Methyl-5-phenyl-3-pentanone;4-Methyl-1-phenyl-3-pentanone
• CAS NO: 40463-09-0
• Molecular Formula: C₁₂H₁₆O
• Molecular Weight: 176.25484
• EINECS: 254-930-9
• Mol File: 40463-09-0.mol

Chemical Properties

• Boiling Point: 254.8 °C at 760 mmHg
• Flash Point: 101 °C
• Appearance: /
• Density: 0.948 /cm³
• Vapor Pressure: 0.0169mmHg at 25°C
• Refractive Index: 1.496
• CAS DataBase Reference: 4-methyl-1-phenylpentan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-1-phenylpentan-3-one(40463-09-0)
• EPA Substance Registry System: 4-methyl-1-phenylpentan-3-one(40463-09-0)

Safety Data

• Hazardous Substances Data: 40463-09-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H16O/c1-10(2)12(13)9-8-11-6-4-3-5-7-11/h3-7,10H,8-9H2,1-2H3

Upstream product

• 2021-28-5 ethyl dihydrocinnamate 
• 1068-55-9 isopropylmagnesium chloride 
• 3160-32-5 (1E)-4-methyl-1-phenylpent-1-en-3-one 
• 79-31-2 isobutyric Acid 
• 501-52-0 3-Phenylpropionic acid 
• 68426-07-3 (+/-)-1-phenyl-5-methylpentan-3-ol 
• 40463-08-9 2,2-dimethyl-3-(2-phenylethyl)oxirane 
• 3277-89-2 phenethylmagnesium bromide 
• 25179-23-1 lithium dimethylacetate 
• 78-82-0 Isobutyronitrile 
• 90878-19-6 phenethylmagnesium chloride 
• 3160-32-5 4-methyl-1-phenyl-1-penten-3-one 
• 144882-91-7 5-phenyl-2-(p-tolylsulfinyl)-3-pentanone 
• 98611-98-4 N-(3-methylbutan-2-ylidene)-1-phenylmethanamine 

Downstream Products

• 260257-61-2 (RS)-3-hydroxy-3-(2-phenethyl)-4-methylpentanoic acid tert-butyl ester 
• 249728-38-9 4-hydroxy-6-isopropyl-6-phenethyl-5,6-dihydro-pyran-2-one 
• 249728-23-2 ethyl-sulfamic acid 5-tert-butyl-4-(4-hydroxy-6-isopropyl-2-oxo-6-phenethyl-5,6-dihydro-2H-pyran-3-ylsulfanyl)-2-methyl-phenyl ester 
• 260257-60-1 (RS)-3-hydroxy-3-(2-phenethyl)-4-methylpentanoic acid 
• 260257-65-6 (R)-3-hydroxy-3-(2-phenethyl)-4-methylpentanoic acid 
• 260257-62-3 (S)-3-hydroxy-3-(2-phenethyl)-4-methylpentanoic acid 
• 260257-94-1 3-(2-tert-butyl-4-hydroxy-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-6-phenethyl-5,6-dihydro-pyran-2-one 
• 263842-69-9 N-[5-tert-butyl-4-(4-hydroxy-6-isopropyl-2-oxo-6-phenethyl-5,6-dihydro-2H-pyran-3-ylsulfanyl)-2-methyl-phenyl]-methanesulfonamide 
• 263842-98-4 pyridine-3-sulfonic acid 5-tert-butyl-4-(4-hydroxy-6-isopropyl-2-oxo-6-phenethyl-5,6-dihydro-2H-pyran-3-ylsulfanyl)-2-methyl-phenyl ester 
• 263842-97-3 pyridine-2-sulfonic acid 5-tert-butyl-4-(4-hydroxy-6-isopropyl-2-oxo-6-phenethyl-5,6-dihydro-2H-pyran-3-ylsulfanyl)-2-methyl-phenyl ester 
• 263842-74-6 thiophene-2-sulfonic acid [5-tert-butyl-4-(4-hydroxy-6-isopropyl-2-oxo-6-phenethyl-5,6-dihydro-2H-pyran-3-ylsulfanyl)-2-methyl-phenyl]-amide 
• 263842-75-7 pyridine-2-sulfonic acid [5-tert-butyl-4-(4-hydroxy-6-isopropyl-2-oxo-6-phenethyl-5,6-dihydro-2H-pyran-3-ylsulfanyl)-2-methyl-phenyl]-amide 
• 263842-72-4 N-[5-tert-Butyl-4-(4-hydroxy-6-isopropyl-2-oxo-6-phenethyl-5,6-dihydro-2H-pyran-3-ylsulfanyl)-2-methyl-phenyl]-4-cyano-benzenesulfonamide 
• 263842-71-3 N-[5-tert-Butyl-4-(4-hydroxy-6-isopropyl-2-oxo-6-phenethyl-5,6-dihydro-2H-pyran-3-ylsulfanyl)-2-methyl-phenyl]-3-cyano-benzenesulfonamide 

Relevant articles and documents

Catalytic Radical Trifluoromethylalkynylation of Unactivated Alkenes

The trifluoromethylalkynylation of unactivated alkenes with alkynyl sulfones and Togni's reagent was developed. The reaction was catalyzed by 2,4,6-trimethylpyridine, leading to various β-trifluoromethylated alkynes under metal-free conditions with a broad substrate scope and wide functional group compatibility. A mechanism involving catalytic nonchain radical processes is proposed.

Visible-Light Decatungstate/Disulfide Dual Catalysis for the Hydro-Functionalization of Styrenes

We describe an efficient photoredox system, relying on decatungstate/disulfide catalysts, for the hydrofunctionalization of styrenes. In this methodology the use of disulfide as a cocatalyst was shown to be crucial for the reaction efficiency. This photoredox system was employed for the hydro-carbamoylation, -acylation, -alkylation, and -silylation of styrenes, giving access to a large variety of useful building blocks and high-value molecules such as amides and unsymmetrical ketones from simple starting materials.

Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide

The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.

Visible-Light-Promoted Catalytic Ring-Opening Isomerization of 1,2-Disubstituted Cyclopropanols to Linear Ketones

Isomerization to linear ketones is a valuable transformation of 1,2-disubstituted cyclopropanols proceeding through radical intermediates. Despite simplicity of this reaction, the known protocol required stoichiometric amounts of both an oxidant and a reducing agent. In this article, we report a catalytic isomerization of 1,2-disubstituted cyclopropanols to linear ketones enabled by the photoredox catalytic system consisting of an acridinium photocatalyst and diphenyl disulfide under irradiation with blue LEDs.

Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N -Iodosuccinimide

Treatment of 2-arylethylmagnesium bromides, prepared from 2-arylethyl bromides and magnesium, with aromatic nitriles, followed by reaction with water and then with N -iodosuccinimide under irradiation with a tungsten lamp, gave the corresponding 2-arylquinolines in good to moderate yields under transition-metal-free conditions. 2-Alkylquinolines could be also obtained in moderate yields by the same procedure with 2-arylethyl bromides, magnesium, aliphatic nitriles bearing a secondary alkyl group, and N -iodosuccinimide.

Conversion of Aldehydes to Branched or Linear Ketones via Regiodivergent Rhodium-Catalyzed Vinyl Bromide Reductive Coupling-Redox Isomerization Mediated by Formate

A regiodivergent catalytic method for direct conversion of aldehydes to branched or linear alkyl ketones is described. Rhodium complexes modified by PtBu2Me catalyze formate-mediated aldehyde-vinyl bromide reductive coupling-redox isomerization to form branched ketones. Use of the less strongly coordinating ligand, PPh3, promotes vinyl-to allylrhodium isomerization en route to linear ketones. This method bypasses the 3-step sequence often used to convert aldehydes to ketones involving the addition of pre-metalated reagents to Weinreb or morpholine amides.

Enamines as Surrogates of Alkyl Carbanions for the Direct Conversion of Secondary Amides to α-Branched Ketones

A direct transformation of secondary amides into α-branched ketones with enamines as soft alkylation reagents was developed. In this reaction, enamines serve as surrogates of alkyl carbanions, rather than the conventional enolates equivalents in the Stork's reactions, which allowed for the easy introduction of alkyl groups with electrophilic functional groups. In the presence of 4 ? molecular sieves, the method can be extended to the one-pot coupling of secondary amides with aldehydes to yield ketones. (Figure presented.).

Radical-Based C?C Bond-Forming Processes Enabled by the Photoexcitation of 4-Alkyl-1,4-dihydropyridines

We report herein that 4-alkyl-1,4-dihydropyridines (alkyl-DHPs) can directly reach an electronically excited state upon light absorption and trigger the generation of C(sp3)-centered radicals without the need for an external photocatalyst. Selective excitation with a violet-light-emitting diode turns alkyl-DHPs into strong reducing agents that can activate reagents through single-electron transfer manifolds while undergoing homolytic cleavage to generate radicals. We used this photochemical dual-reactivity profile to trigger radical-based carbon–carbon bond-forming processes, including nickel-catalyzed cross-coupling reactions.

Alkylation of Ketones Catalyzed by Bifunctional Iron Complexes: From Mechanistic Understanding to Application

Cyclopentadienone iron dicarbonyl complexes were applied in the alkylation of ketones with various aliphatic and aromatic ketones and alcohols via the borrowing hydrogen strategy in mild reaction conditions. DFT calculations and experimental works highlight the role of the transition metal Lewis pairs and the base. These iron complexes demonstrated a broad applicability in mild conditions and extended the scope of substrates.

Method for synthesizing alpha-alkyl ketone

The invention discloses a method for synthesizing alpha-alkyl ketone, and especially includes the following steps of: in a reaction vessel, adding secondary alcohol, a transition metal catalyst, and a solvent tertiary amyl alcohol; and heating and refluxing a reaction mixture in an oil bath for several hours, cooling the mixture to a room temperature; then adding primary alcohol and alkali, heating and refluxing the reaction mixture for several hours, and then obtaining a target compound through column separation. The method for synthesizing the alpha-alkyl ketone starts from the primary alcohol and the secondary alcohol. With the participation of the transition metal catalyst, the alpha-alkyl ketone is generated through a serial secondary alcohol non-acceptor dehydrogenation oxidation reaction/alpha-alkylation reaction of ketone. The reaction shows three obvious advantages that 1) non-toxic alcohols are used as the starting materials; 2) only hydrogen and water are generated in the reaction without environmental hazards; 3) atomic economy is high in the reaction; and 4) only 0.1 equivalents of carbonate is needed for the reaction, and the reaction only takes 3-6 hours. Therefore, the reaction meets the requirements of green chemistry and has broad development prospects.