2050-07-9

Usage

Uses

Used in Pharmaceutical Industry:
4-methyl-1-phenylpentan-1-one is used as an intermediate in the synthesis of a-Pyrrolidinoisohexanophenone (Hydrochloride) (P841230), which is a phenone derivative. This derivative is utilized for research purposes, particularly in the development of new pharmaceutical compounds and drugs. The compound plays a crucial role in the synthesis process due to its unique structural features and reactivity.
Used in Chemical Research:
In the field of chemical research, 4-methyl-1-phenylpentan-1-one serves as a valuable compound for studying the properties and reactions of ketones, as well as exploring the potential for new chemical reactions and applications. Its unique structure allows researchers to investigate various aspects of organic chemistry, including the effects of substituents on reactivity and the potential for functional group transformations.
Used in Flavor and Fragrance Industry:
Due to its distinct chemical structure, 4-methyl-1-phenylpentan-1-one may also find applications in the flavor and fragrance industry. The compound could be used as a starting material for the synthesis of various aroma compounds or as a component in the creation of complex fragrances. Its unique scent profile and chemical properties make it a potential candidate for use in the development of new and innovative fragrances.

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

Upstream product

• 334992-48-2 isopentylmagnesium iodide 
• 100-47-0 benzonitrile 
• 7316-69-0 1-phenyl-4-methyl-2-penten-1-one 
• 63942-77-8 B-iso-butyl-9-borabicyclo<3.3.1>nonane 
• 70-11-1 α-bromoacetophenone 
• 71-43-2 benzene 
• 1116-40-1 triisobutylamine 
• 98-86-2 acetophenone 
• 6898-82-4 N-isobutylideneisobutylamine 
• 78-83-1 2-methyl-propan-1-ol 
• 98-85-1 1-Phenylethanol 
• 78-77-3 Isobutyl bromide 
• 13466-32-5 acetophenone dimethylhydrazone 
• 6919-61-5 N-methoxy-N-methylbenzamide 

Downstream Products

• 7415-77-2 3-Benzoyl-2-ethoxycarbonyl-5-methyl-hexansaeure-ethylester 
• 81759-40-2 2,2-dimethyl-1-phenyl-1-cyclobutanol 
• 86259-54-3 1-phenyl-1-methoxy-4-methylpentane 
• 98-86-2 acetophenone 
• 169602-00-0 5,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one 
• 115-11-7 isobutene 
• 244091-30-3 Trimethyl-((Z)-4-methyl-1-phenyl-pent-1-enyloxy)-silane 
• 2979-69-3 3,4-dihydro-4,4-dimethyl-1(2H)-naphthalenone 
• 117861-42-4 4-hydroxy-4-methyl-1-phenyl-1-pentanone 
• 1027549-15-0 2-(2-Hydroxy-1,1-dimethyl-ethylamino)-4-methyl-1-phenyl-pentan-1-ol 

Relevant academic research and scientific papers

KOtBu/DMSO Catalytic System for Isomerization of Allylic Alcohols to Ketones

The isomerization of allylic alcohols is an important reaction because it can afford carbonyl compounds in an atom-economical manner. Although base-catalyzed methods are more desirable than those using transition-metal catalysts from both the economic and environmental points of view, these methods have several drawbacks, such as narrow substrate scope and high catalyst loading. This paper reports the development of an efficient KOtBu/DMSO catalytic system suitable for the isomerization of a broad range of allylic alcohols with good yields, to which previously reported systems could not be applied. This catalytic system was successfully applied to a tandem allylic isomerization/electrophilic trapping reaction, thereby highlighting its synthetic utility.

Iron-Catalyzed, Iminyl Radical-Triggered Cascade 1,5-Hydrogen Atom Transfer/(5+2) or (5+1) Annulation: Oxime as a Five-Atom Assembling Unit

By integration of iminyl radical-triggered 1,5-hydrogen atom transfer and (5+2) or (5+1) annulation processes, a series of structurally novel and interesting azepine and spiro-tetrahydropyridine derivatives have been successfully prepared in moderate to good yields. This method utilizes FeCl2 as the catalyst and readily available oximes as five-atom units, while showcasing broad substrate scope and good functional group compatibility. The annulation products can be easily converted into many valuable compounds. Moreover, DFT calculation studies are performed to provide some insights into the possible reaction mechanisms for the (5+2) and (5+1) annulations.

Copper-Catalyzed Oxidative Fragmentation of Alkynes with NFSI Provides Aryl Ketones

A copper-catalyzed oxidative cleavage reaction of alkynes using NFSI and TBHP was described. Various terminal and internal alkyne substrates were employed to render quick access to aryl ketone products in moderate to good yields. NFSI not only functioned as N-centered radical precursors but also engaged in the aryl group migration. Mechanistic studies also suggested the important role of water in the title reactions.

Mn-Enabled Radical-Based Alkyl-Alkyl Cross-Coupling Reaction from 4-Alkyl-1,4-dihydropyridines

Highly efficient alkylation of β-chloro ketones and their derivatives was achieved by means of domino dehydrochlorination/Mn-enabled radical-based alkyl-alkyl cross-coupling reaction. In situ-generated α,β-unsaturated ketones and their analogues were identified as the reaction intermediates. Known bioactive compounds, such as melperone and azaperone, could be easily prepared from β-chloropropiophenone in two steps.

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates

Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.

Iron-Catalyzed Synthesis of Dihydronaphthalenones from Aromatic Oxime Esters

Herein, a convenient procedure on iron-catalyzed radical-mediated synthesis of dihydronaphthalenones from oxime esters has been developed. By using iron salt as a green and inexpensive catalyst, various α-aryl oxime esters were transformed into the corresponding dihydronaphthalenones in moderate to good yields with high chemo-selectivities. The reaction proceeds via 1,5-hydrogen atom transfer and then intramolecular radical cyclization sequence. (Figure presented.).

Iron-Catalysed Remote C(sp3)?H Azidation of O-Acyl Oximes and N-Acyloxy Imidates Enabled by 1,5-Hydrogen Atom Transfer of Iminyl and Imidate Radicals: Synthesis of γ-Azido Ketones and β-Azido Alcohols

In the presence of a catalytic amount of iron(III) acetylacetonate [Fe(acac)3], the reaction of structurally diverse ketoxime esters with trimethylsilyl azide (TMSN3) afforded γ-azido ketones in good to excellent yields. This unprecedented distal γ-C(sp3)?H bond azidation reaction went through a sequence of reductive generation of an iminyl radical, 1,5-hydrogen atom transfer (1,5-HAT) and iron-mediated redox azido transfer to the translocated carbon radical. TMSN3 served not only as a nitrogen source to functionalise the unactivated C(sp3)?H bond, but also as a reductant to generate the catalytically active FeII species in situ. Based on the same principle, a novel β-C(sp3)?H functionalisation of alcohols via N-acyloxy imidates was subsequently realised, leading, after hydrolysis of the resulting ester, to β-azido alcohols, which are important building blocks in organic and medicinal chemistry.

Regioselective Vinylation of Remote Unactivated C(sp3)?H Bonds: Access to Complex Fluoroalkylated Alkenes

Regioselective incorporation of a particular functional group into aliphatic sites by direct activation of unreactive C?H bonds is of great synthetic value. Despite advances in radical-mediated functionalization of C(sp3)?H bonds by a hydrogen-atom transfer process, the site-selective vinylation of remote C(sp3)?H bonds still remains underexplored. Reported herein is a new protocol for the regioselective vinylation of unactivated C(sp3)?H bonds. The remote C(sp3)?H activation is promoted by a C-centered radical instead of the commonly used N and O radicals. The reaction possesses high product diversity and synthetic efficiency, furnishing a plethora of synthetically valuable E alkenes bearing tri-/di-/mono-fluoromethyl and perfluoroalkyl groups.

Iminyl Radical-Triggered Intermolecular Distal C(sp3)-H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade

An efficient iron-catalyzed intermolecular remote C(sp3)-H heteroarylation of alkyl ketones has been developed via an iminyl radical-triggered 1,5-hydrogen-atom transfer (HAT) cascade. This protocol was amenable to a wide variety of alkyl ketones and heteroaryls, thus providing a straightforward method for the late-stage functionalization of alkylketones and heteroaryls.

Carbonylation of tertiary carbon radicals: synthesis of lactams

Herein, we disclose an interesting iron-catalyzed approach for the carbonylation of a tertiary carbon radical. The tertiary carbon radical generated from a 1,5-hydrogen atom transfer can be captured by CO gas smoothly. Various six-membered lactams were constructed chemo-selectively in high yields.