6263-83-8

Usage

Uses

1. Used in Electrochemical Synthesis:
1,5-Diphenyl-1,5-pentanedione is used as a precursor in the electrochemical synthesis of cis-1,2-diphenyl-1,2-cyclopentanediol. 1,5-DIPHENYL-1,5-PENTANEDIONE serves as a key intermediate in the production of this important organic compound, which has various applications in the chemical industry.
2. Used in Pharmaceutical Industry:
1,5-Diphenyl-1,5-pentanedione can be utilized as a building block for the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of novel molecules with potential therapeutic properties.
3. Used in Chemical Research:
As an organic compound with distinct chemical properties, 1,5-diphenyl-1,5-pentanedione can be employed in various research applications to study its reactivity, stability, and potential interactions with other molecules. This can lead to the discovery of new chemical reactions and the development of innovative synthetic methods.
4. Used in Material Science:
1,5-DIPHENYL-1,5-PENTANEDIONE's crystalline nature and unique structure make it a candidate for use in the development of new materials with specific properties, such as improved conductivity, strength, or thermal stability.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 901, 1973 DOI: 10.1021/jo00945a011Tetrahedron Letters, 15, p. 3721, 1974

InChI:InChI=1/C17H16O2/c18-16(14-8-3-1-4-9-14)12-7-13-17(19)15-10-5-2-6-11-15/h1-6,8-11H,7,12-13H2

Upstream product

• 93436-35-2 1,2-diphenyl-cyclopentane 
• 50-00-0 formaldehyd 
• 98-86-2 acetophenone 
• 3506-36-3 3-dimethylaminopropiophenone 
• 2873-74-7 gloutaric dichloride 
• 71-43-2 benzene 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 4747-13-1 α-methoxystyrene 
• 29526-96-3 1-phenylcyclopropan-1-ol 
• 66324-10-5 tert-butyldimethyl(1-phenylvinyloxy)silane 
• 73258-08-9 1,2-diphenylcyclopentene ozonide 
• 133549-24-3 2-(3-benzoylpropyl)-2-phenyl-1,3-dioxolane 
• 68-12-2 N,N-dimethyl-formamide 
• 27905-65-3 2,6-Diphenyl-1,6-heptadiene 

Downstream Products

• 63634-88-8 (1-Hydroxy-5-oxo-1,5-diphenylpentyl)-phosphonige Saeure 
• 62329-00-4 1,5-Diphenyl-5-(dicyanomethylen)-1-pentanon 
• 20030-69-7 1,2-dibenzoyl-cyclopropane 
• 123895-05-6 2-hydroxy-1,5-diphenyl-1,5-pentanedione 
• 123895-07-8 methyl 5-oxo-2,5-diphenylpentanoate 
• 109240-27-9 1,7-Diiodo-2,6-diphenyl-heptane-2,6-diol 
• 126708-35-8 <1-Hydroxy-1,5-diphenyl-5-(trimethylsiloxy)pentamethylene>bisphosphonous Acid 
• 26057-47-6 (E,E)-1,5-diphenyl-1,4-pentadiene 
• 28069-36-5 (E)-1,5-diphenylpent-4-en-1-one 
• 143536-22-5 2,6-diphenyl-2,3-dihydropyran 
• 56568-43-5 1,5-diphenyl-2,4-dibromo-1,5-pentanedione 
• 3558-68-7 2,6-diphenylpyrylium perchlorate 
• 13586-29-3 2,6-diphenylthiopyrilium perchlorate 
• 96282-41-6 2,6-Diphenyl-tetrahydro-selenopyran 

Relevant academic research and scientific papers

Iron-Catalyzed Ring-Opening Reactions of Cyclopropanols with Alkenes and TBHP: Synthesis of 5-Oxo Peroxides

The ring opening of cyclopropanols is rarely used in multicomponent reactions. Herein we report the three-component reaction of cyclopropanols with alkenes and tert-butyl hydroperoxide (TBHP) catalyzed by an iron catalyst. This protocol enables the incorporation of both the β-carbonyl fragment and a peroxy unit across the C=C double bond regioselectively, thus allowing an efficient, facile access to 5-oxo peroxides. Modification of the biologically active molecules and various downstream derivatizations of the peroxides are also demonstrated.

Ruthenium-Catalyzed Alkylation of Cyclopropanols with Sulfoxonium Ylides via C-C Bond Cleavage: Formation of Diverse 1,5-Diketones

A novel ruthenium-catalyzed alkylation of cyclopropanols with sulfoxonium ylides has been developed that affords diverse 1,5-diketones with good efficiency and broad substrate scope. To illustrate the synthetic applications of the obtained 1,5-diketones, aldol and cyclization reactions have been investigated. Preliminary mechanistic studies suggest that this process involves a sequential C C activation and carbene migratory insertion.

Ruthenium-catalyzed room-temperature coupling of α-keto sulfoxonium ylides and cyclopropanols for δ-diketone synthesis

Previous transition metal-catalyzed synthesis processes of δ-diketones are plagued by the high cost of the rhodium catalyst and harsh reaction conditions. Herein a low-cost, room temperature ruthenium catalytic method is developed based on the coupling of α-keto sulfoxonium ylides with cyclopropanols. The mild protocol features a broad substrate scope (47 examples) and a high product yield (up to 99%). Mechanistic studies argue against a radical pathway and support a cyclopropanol ring opening, sulfoxonium ylide-derived carbenoid formation, migratory insertion C-C bond formation pathway.

Palladium mediated one-pot synthesis of 3-aryl-cyclohexenones and 1,5-diketones from allyl alcohols and aryl ketones

One-pot synthesis of Robinson annulated 3-aryl-cyclohexenones from allyl alcohols and ketones using palladium is reported. Long chain aliphatic or aryl substitutions at the C1 position of allyl alcohol result in the formation of 1,5-diketone products. This simple one-pot method avoids the use of highly electrophilic vinyl ketones.

Ruthenium-catalyzed alkylation reaction of cyclopropanol and sulfur ylide for synthesis of 1, 5-diketone compounds

The invention relates to a ruthenium-catalyzed alkylation reaction of cyclopropanol and sulfur ylide, and a series of 1, 5-diketone compounds can be synthesized by the method. According to the method,cyclopropanol is catalyzed by ruthenium to generate beta-carbon elimination ring opening, and safe, stable and easy-to-prepare sulfur ylide is used as a carbene precursor, so that the method has goodapplicability in the field of construction of 1, 5-diketone.

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.

Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds

Visible light-induced organic reactions are important chemical transformations in organic chemistry, and their efficiency highly depends on suitable photocatalysts. However, the commonly used photocatalysts are precious transition-metal complexes and elaborate organic dyes, which hamper large-scale production due to high cost. Here, for the first time, we report a novel strategy: light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds, allowing high-value-added aromatic ketones and carboxylic acids to be easily prepared in high-to-excellent yields using readily available alkyl arenes, methyl arenes and aldehydes as materials. The mechanistic investigations showed that the treatment of inexpensive and readily available sodium trifluoromethanesulfinate with oxygen under irradiation of light could in situ form a pentacoordinate sulfide intermediate as an efficient photosensitizer. The method represents a highly efficient, economical and environmentally friendly strategy, and the light and oxygen-enabled sodium trifluoromethanesulfinate photocatalytic system represents a breakthrough in photochemistry. This journal is

Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles

The first example of the Pd-catalyzed addition of organoboron reagents to dinitriles, as an efficient means of preparing 2,5-diarylpyrroles and 2,6-diarylpyridines, has been discussed here. Furthermore, the highly selective carbopalladation of dinitriles with organoboron reagents to give long-chain ketonitriles has been developed as well. Based on the broad scope of substrates, excellent functional group tolerance, and use of commercially available substrates, the Pd-catalyzed addition reaction of arylboronic acid and dinitriles is expected to be significant in future synthetic procedures.

Photoredox-Catalyzed Decarboxylative Alkylation of Silyl Enol Ethers to Synthesize Functionalized Aryl Alkyl Ketones

Photoredox-catalyzed decarboxylative alkylation of silyl enol ethers has been developed. Diverse functionalized aryl alkyl ketones were afforded in modest to good yields using N-(acyloxy)phthalimide as an easy access alkyl radical source under mild and operationally simple conditions. The excellent performance of drug molecules such as fenbufen and indomethacin and naturally occurring carboxylic acids such as stearic acid and dehydrocholic acid further demonstrated the practicability of the reaction.

Synthetic studies on a series of functionalized pyrylium salts, 4-chloro- and 4-bromophosphinines

A series of new pyrylium salts that bear sulfonate and phosphonate groups were obtained from the reactions between 2,6-diphenyl-4H-pyran-4-one, sulfonic anhydride, and chlorophosphates, and analyzed spectroscopically. Furthermore, treatment of 2,6-diphenyl-4H-pyran-4-one with phosphoryl chloride or bromide afforded the corresponding 4-chloro- and 4-bromopyrylium tetrafluoroborates in good yield. Subsequently, the synthesis of the corresponding 4-chloro- and 4-bromophosphinines was accomplished by treating the respective chloro- and bromopyrylium tetrafluoroborates with tris(trimethylsilyl)phosphine.