6303-82-8

Usage

Structure

Diketone It contains two carbonyl functional groups (C=O) within its molecular structure.

Appearance

Yellowish crystalline solid The compound has a yellowish hue and a solid, crystalline form.

Odor

Sweet, fruity 1-Phenylhexane-1,5-dione has a pleasant, sweet, and fruity smell.

Usage

Reagent in organic synthesis and pharmaceutical manufacturing It is commonly used in the synthesis of other organic compounds and in the production of pharmaceuticals.

Usage

Flavoring agent in the food industry 1-Phenylhexane-1,5-dione is used to add flavor to various food products.

Safety

Potential skin irritant The compound may cause skin irritation and should be handled with care.

Upstream product

• 5978-08-5 1-chloro-4-(1,3-dioxolane)-n-pentane 
• 6907-73-9 N-(α-methylbenzylidene)isopropylamine 
• 78-94-4 methyl vinyl ketone 
• 98-86-2 acetophenone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 67935-23-3 trans-3-methoxybut-2-en-1-ol 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 29526-96-3 1-phenylcyclopropan-1-ol 
• 4747-13-1 α-methoxystyrene 
• 22524-25-0 1-phenylhex-5-en-1-one 
• 62248-76-4 6-phenyl-5-hexyn-2-one 
• 53857-10-6 4-(2-methyl-[1,3]dioxolan-2-yl)-1-phenyl-butan-1-one 
• 88072-88-2 2-Nitro-1-phenyl-hexane-1,5-dione 
• 291525-41-2 1-phenyl-2-trifluoroacetyl-1,5-hexanedione 

Downstream Products

• 4810-10-0 1-(2-methylcyclopent-1-enyl)benzene 
• 10345-87-6 3-phenylcyclohex-2-enone 
• 25444-79-5 3-hydroxy-3-phenylcyclohexanone 
• 719272-47-6 trans-1-methyl-2-phenylcyclopentane-1,2-diol 
• 719272-47-6 cis-1-methyl-2-phenylcyclopentane-1,2-diol 
• 46181-30-0 6-methyl-2-phenylpyridine 
• 1393343-68-4 (2S)-2-methyl-6-phenyl-2,3,4,5-tetrahydropyridine 
• 1393343-69-5 (2R)-2-methyl-6-phenyl-2,3,4,5-tetrahydropyridine 
• 214267-62-6 (2R,6R)-(+)-2-methyl-6-phenylpiperidine 
• 20795-53-3 3-phenylcyclohexanone 
• 1186225-45-5 (S)-3-hydroxy-3-phenylcyclohexan-1-one 
• 25444-79-5 3-Hydroxy-3-phenylcyclohexanon 

Relevant academic research and scientific papers

Ir(NHC)-Catalyzed Synthesis of β-Alkylated Alcohols via Borrowing Hydrogen Strategy: Influence of Bimetallic Structure

Multi N-heterocyclic carbene(NHC)-modified iridium catalysts were employed in the β-alkylation of alcohols; dimerization of primary alcohols (Guerbet reaction), cross-coupling of secondary and primary alcohols, and intramolecular cyclization of alcohols. Mechanistic studies of Guerbet reaction, including kinetic experiments, mass analysis, and density functional theory (DFT) calculation, were employed to explain the fast reaction promoted by bimetallic catalysts, and the dramatic reactivity increase of monometallic catalysts at the late stage of the reaction. (Figure presented.).

Oxidative Cleavage of Alkenes by O2with a Non-Heme Manganese Catalyst

The oxidative cleavage of C═C double bonds with molecular oxygen to produce carbonyl compounds is an important transformation in chemical and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C═C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atmospheric pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asymmetric, mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.

Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis

Here we report the first example of alkyne trifunctionalization through simultaneous construction of C-C, C-O, and C-N bonds via gold catalysis. With the assistance of a γ-keto directing group, sequential gold-catalyzed alkyne hydration, vinyl-gold nucleophilic addition, and gold(III) reductive elimination were achieved in one pot. Diazonium salts were identified as both electrophiles (N source) and oxidants (C source). Vinyl-gold(III) intermediates were revealed as effective nucleophiles toward diazonium, facilitating nucleophilic addition and reductive elimination with high efficiency. The rather comprehensive reaction sequence was achieved with excellent yields (up to 95%) and broad scope (>50 examples) under mild conditions (room temperature or 40 °C).

Regioselective Crossed Aldol Reactions under Mild Conditions via Synergistic Gold-Iron Catalysis

A synergistic gold-iron (Au-Fe) catalytic system was developed for sequential alkyne hydration and vinyl Au addition to aldehydes or ketones. Fe(acac)3 was identified as an essential co-catalyst in preventing vinyl Au protodeauration and facilitating nucleophilic additions. Effective C–C bond formation was achieved under mild conditions (room temperature) with excellent regioselectivity and high efficiency (1% [Au], up to 95% yields). The intramolecular reaction was also achieved, giving successful macrocyclization (16–31 ring sizes) with excellent yields (up to 90%, gram scale) without extended dilution (0.2 M), which highlights the great potential of this new crossed aldol strategy in challenging target molecule synthesis. Effective construction of the C–C bond is one of the most important tasks in organic synthesis. Whereas aldol condensation is a classic C–C bond-forming transformation, it requires other chemical promoters, such as strong base and reactive acidic catalysts. As a result, the overall transformation is limited in terms of ideal atom economy and environmentally friendly operation. With the discovery of a gold-iron (Au-Fe) synergistic catalysis system, here we describe a new approach to facilitating alkyne hydration and sequential vinyl Au addition to carbonyls. This approach gives the C–C bond-forming products in excellent yields, wide substrate scope, and great functional-group compatibility under mild conditions. This protocol can also be applied to macrocyclization without extended dilution. This C–C bond-forming strategy could facilitate challenging molecule synthesis in chemical, biological, and medicinal research. We report a synergistic gold-iron (Au-Fe) catalytic system to access vinyl Au reactivity by avoiding frequently occurring protodeauration. Fe(acac)3 was identified as an essential co-catalyst, facilitating vinyl Au addition to aldehydes. A broad substrate scope was obtained under mild conditions (room temperature) with excellent regioselectivity and high efficiency (1% [Au], up to 95% yields). This protocol offers a practical solution for achieving macrocyclization (16–31 ring sizes, up to 90%, gram scale) without extended dilution, highlighting the synthetic utility in complex molecular synthesis.

Photo-mediated [1, 3]-Carbonyl shift of β-Ketocarbonyls

An organic amine mediated photolytic [1,3]-benzoyl migration of β-benzoyl carbonyl compounds was reported. This migration was achieved by Norrish-Yang cyclization and retro-aldol reaction under black light (365 nm) or visible light irradiation. This photolytic protocol provides an alternative approach to the synthesis of 1,5-dicarbonyl compounds. By chiral primary amine catalysis, a kinetic resolution was also developed to afford enantioenriched 1,5-dicarbonyls.

Nonclassical Mechanism in the Cyclodehydration of Diols Catalyzed by a Bifunctional Iridium Complex

1,4- and 1,5-diols undergo cyclodehydration upon treatment with cationic N-heterocyclic carbene (NHC)–IrIII complexes to give tetrahydrofurans and tetrahydropyrans, respectively. The mechanism was investigated, and a metal-hydride-driven pathway was proposed for all substrates, except for very electron-rich ones. This contrasts with the well-established classical pathways that involve nucleophilic substitution.

Cyclopentane Formation from Flexible Precursors Using Samarium(II) Reagents

Three efficient methods for five-membered ring carbocycle synthesis have been developed from simple starting materials using samarium(II) reagents. A Reformatsky aldol reaction proceeded efficiently with samarium(II) iodide using lithium bromide as an additive. A new intramolecular alkylation of a samarium enolate was realized with a pendant sulfonate ester leaving group. Pinacol cyclization of a simple diketone was also demonstrated giving a diol product in high stereoselectivity. A promising lead result has been established demonstrating enantioselectivity in a chiral ligand controlled Reformatsky aldol reaction.

Synthesis of Benzofurans from Ketones and 1,4-Benzoquinones

Benzofuran derivatives can be synthesized through the sequential Michael addition and cyclization of 1,3-dicarbonyl compounds with 1,4-benzoquinones. However, ketones are rarely used in this reaction because of their low nucleophilicities. In this study, this problem was solved by utilizing triethyl orthoformate, which enabled the formation of a vinyl ethyl ether as an additive. As a result, the nucleophilicity of ketones increased. Many important 5-hydroxybenzofuran derivatives, which were not readily available by synthesis in the past, were also prepared via these newly established reactions. (Figure presented.) .

Bimetallic nanosized solids with acid and redox properties for catalytic activation of C-C and C-H bonds

A new approach is presented to form self-supported bimetallic nanosized solids with acid and redox catalytic properties. They are water-, air- and H2-stable, and are able to activate demanding C-C and C-H reactions. A detailed mechanistic study on the formation of the Ag-Fe bimetallic system shows that a rapid redox-coupled sequence between Ag+, O2 (air) and Fe2+ occurs, giving monodisperse Ag nanoparticles supported by O-bridged diatomic Fe3+ triflimides. The system can be expanded to Ag nanoparticles embedded within a matrix of Cu2+, Bi3+ and Yb3+ triflimide.

Palladium-Catalyzed Long-Range Deconjugative Isomerization of Highly Substituted α,β-Unsaturated Carbonyl Compounds

The long-range deconjugative isomerization of a broad range of α,β-unsaturated amides, esters, and ketones by an in situ generated palladium hydride catalyst is described. This redox-economical process is triggered by a hydrometalation event and is thermodynamically driven by the refunctionalization of a primary or a secondary alcohol into an aldehyde or a ketone. Di-, tri-, and tetrasubstituted carbon-carbon double bonds react with similar efficiency; the system is tolerant toward a variety of functional groups, and olefin migration can be sustained over 30 carbon atoms. The refunctionalized products are usually isolated in good to excellent yield. Mechanistic investigations are in support of a chain-walking process consisting of repeated migratory insertions and β-H eliminations. The bidirectionality of the isomerization reaction was established by isotopic labeling experiments using a substrate with a double bond isolated from both terminal functions. The palladium hydride was also found to be directly involved in the product-forming tautomerization step. The ambiphilic character of the in situ generated [Pd-H] was demonstrated using isomeric trisubstituted α,β-unsaturated esters. Finally, the high levels of enantioselectivity obtained in the isomerization of a small set of α-substituted α,β-unsaturated ketones augur well for the successful development of an enantioselective version of this unconventional isomerization.