10413-00-0

Usage

Uses

Used in Pharmaceutical Synthesis:
5-OXO-5-PHENYLVALERONITRILE is used as a precursor in the pharmaceutical industry for the synthesis of various medications. Its role in the creation of active pharmaceutical ingredients is crucial, as it can be transformed into different compounds with therapeutic properties.
Used in Perfume Production:
In the fragrance industry, 5-OXO-5-PHENYLVALERONITRILE is utilized as a precursor to create various scent compounds. Its aromatic characteristics make it valuable in the development of perfumes and other scented products.
Used in Research and Development Laboratories:
5-OXO-5-PHENYLVALERONITRILE is employed as an intermediate in organic synthesis within research and development settings. It is instrumental in the exploration of new chemical reactions and the creation of novel compounds for various applications.

InChI:InChI=1/C11H11NO/c12-9-5-4-8-11(13)10-6-2-1-3-7-10/h1-3,6-7H,4-5,8H2

Upstream product

• 5415-48-5 2-benzoyl-4-cyano-butyric acid ethyl ester 
• 91132-81-9 5-oxo-5-phenyl-valeric acid amide 
• 143-33-9 sodium cyanide 
• 107-13-1 acrylonitrile 
• 98-86-2 acetophenone 
• 5342-96-1 4-benzoyl-4-(2-cyanoethyl)heptanedinitrile 
• 58422-71-2 α-Peracetoxy-α-phenylvaleronitril 
• 6727-73-7 4-iodobutyronitrile 
• 98-88-4 benzoyl chloride 
• 5332-06-9 4-bromobutanenitrile 
• 30077-68-0 ethyl 2-cyano-5-oxo-5-phenylpentanoate 
• 120-92-3 cyclopentanone 
• 70969-99-2 1,1-Ethylenedioxy-4-iodo-1-phenylbutane 
• 1501-04-8 Methyl 4-benzoylbutanoate 

Downstream Products

• 19006-82-7 2-hydroxy-6-phenylpyridine 
• 34502-63-1 6-Phenyl-1,2,3,4-tetrahydropyridin-2-on 
• 3466-80-6 2-phenylpiperidine 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 104850-13-7 5-phenyl-5-semicarbazono-valeronitrile 
• 88687-19-8 5-(4-Methyl-3-nitro-phenyl)-1,3,4,5-tetrahydro-indeno[1,2-b]pyridin-2-one 
• 81152-86-5 5-(2-Trifluoromethyl-phenyl)-1,3,4,5-tetrahydro-indeno[1,2-b]pyridin-2-one 
• 88687-17-6 5-p-Tolyl-1,3,4,5-tetrahydro-indeno[1,2-b]pyridin-2-one 
• 81152-84-3 5-(4-Fluoro-phenyl)-1,3,4,5-tetrahydro-indeno[1,2-b]pyridin-2-one 
• 81152-83-2 5-(4-Chloro-phenyl)-1,3,4,5-tetrahydro-indeno[1,2-b]pyridin-2-one 
• 81152-87-6 5-(4-nitrophenyl)-1,2,3,4-tetrahydro-5H-indeno<1,2-b>pyridin-2-one 
• 81152-82-1 5-Phenyl-1,2,3,4-tetrahydro-5H-indeno<1,2-b>pyridin-2-on 
• 81152-88-7 5-(4-Methoxy-phenyl)-1,3,4,5-tetrahydro-indeno[1,2-b]pyridin-2-one 
• 88687-24-5 5-(2-Fluoro-phenyl)-1,3,4,5-tetrahydro-indeno[1,2-b]pyridin-2-one 

Relevant academic research and scientific papers

Enhanced structural variety of nonplanar N-oxyl radical catalysts and their application to the aerobic oxidation of benzylic C-H bonds

The design and synthesis of structurally variable, nonplanar N-oxyl radical catalysts and their application to the aerobic oxidation, etherification, and acetoamidation of benzylic C-H bonds are described. The catalytic oxidation of C-H bonds represents a powerful tool to synthesize oxygenated functional molecules from simple hydrocarbons in a straightforward way. Electron-deficient N-oxyl radical catalysts, such as phthalimidoyl N-oxyl (PINO) radical, generated from N-hydroxyphthalimide (1), have attracted much attention because of their applications in the oxidation of C-H bonds with high bond dissociation energy (BDE). However, a few sites in 1 are available for structural modifications and improvements of the catalytic performance. By replacing one carbonyl group in 1 with a trifluoromethyl (CF3)-substituted sp3-carbon, we generated an additional tunable site and a nonplanar backbone, while retaining the desirable electron-withdrawing properties and increasing the lipophilicity with respect to 1. We synthesized a variety of N-hydroxy pre catalysts containing such a CF3 moiety, and investigated their utility in the aerobic oxidation of benzylic C-H bonds. Precatalysts with electron-withdrawing substituents, such as trifluoroethoxy and the acetophenone moieties, afforded higher yields than a corresponding methoxy-substituted analogue. The introduction of substituents at the aromatic ring was also effective, as evident from the performance of 7-CF3 and 4,5,6,7-tetrafluoro precatalysts. Especially the combination of trifluoroethoxy- and 4,5,6,7-tetrafluoro substitution afforded a superior performance. These catalyst systems exhibited high functional group tolerance during the aerobic oxidation of C-H bonds, and benzylic etherification and Ritter-type reactions could be carried out at room temperature when a selected precatalyst and N-bromosuccinimide (NBS) were used.

Cobalt-Catalyzed Aerobic Oxidative Cleavage of Alkyl Aldehydes: Synthesis of Ketones, Esters, Amides, and α-Ketoamides

A widely applicable approach was developed to synthesize ketones, esters, amides via the oxidative C?C bond cleavage of readily available alkyl aldehydes. Green and abundant molecular oxygen (O2) was used as the oxidant, and base metals (cobalt and copper) were used as the catalysts. This strategy can be extended to the one-pot synthesis of ketones from primary alcohols and α-ketoamides from aldehydes.

Visible-light-promoted site-specific and diverse functionalization of a c(sp3)-c(sp3) bond adjacent to an arene

We report here a strategy for inert C-C bond functionalization. Site-specific cleavage and functionalization of a saturated C(sp3)-C(sp3) bond via a visible-light-induced radical process have been achieved. The general features of this reaction are as follows. (1) Both linear and cyclic C(sp3)-C(sp3) bonds with a vicinal arene can be specifically functionalized. (2) One carbon is converted into a ketone, and another can be tunably converted into nitrile, peroxide, or halide. (3) The typical conditions include 1.0 mol % of Ru(bpy)3Cl2, 1.0 or 5.0 equiv of Zhdankin reagent, white CFL (24 W), open flask, and room temperature. These reactions offer powerful tools to modify carbon skeletons that are intractable by conventional methods. Good selectivity and functional group tolerance, together with mild and open air conditions, make these transformations valuable and attractive.

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.

Palladium-Catalyzed Cascade Reactions of I-Ketonitriles with Arylboronic Acids: Synthesis of Pyridines

This study presents the first example of the Pd-catalyzed cascade reactions of 5-oxohexanenitrile with arylboronic acids, affording important synthon 2-methylpyridines that can be further translated through C(sp3)-H functionalization to construct pyridine derivatives. Furthermore, this chemistry allows 5-oxo-5-Arylpentanenitrile to react with arylboronic acids to provide unsymmetrical 2,6-diarylpyridines. This protocol paves the way for the practical and atom economical syntheses of valuable pyridines with broad functional groups in moderate to excellent yields under mild conditions.

Photoinduced C—C Bond Cleavage and Oxidation of Cycloketoxime Esters

A novel structural reorganization of cycloketoxime esters beyond the traditional Beckmann rearrangement process has been established to build cyano-containing ketones in the presence of photocatalyst. This novel transformation is remarkable with selective C—C bond cleavage and an oxidation process enabled by DMSO used as the solvent, oxidant, and oxygen source avoiding acid, base and toxic cyanide salts as the cyano source. Further applications in late-stage modification of complex and chiral molecules have also been reported.

Nickel-Catalyzed Reductive Electrophilic Ring Opening of Cycloketone Oxime Esters with Aroyl Chlorides

By merging cross-electrophile coupling and C-C bond cleavage, we developed a Ni-catalyzed electrophilic ring opening of cycloketone oxime esters with aromatic acid chlorides in assistance of Mn as reductant. Notably, complete regioselectivity can be achieved in this C-C bond cleavage reaction, providing an efficient access to a variety of cyanoketones under cyanide-free conditions. A radical reaction pathway was proposed on the basis of the results of the mechanistic probing experiments.

C-C Bond-Forming Strategy by Manganese-Catalyzed Oxidative Ring-Opening Cyanation and Ethynylation of Cyclobutanol Derivatives

A novel C-C bond-forming strategy employing manganese-catalyzed ring-opening of cyclobutanol substrates, followed by cyanation or ethynylation, is described. A cyano C1 unit and ethynyl C2 unit are regiospecifically introduced to the γ-position of ketones at room temperature, providing a mild yet powerful method for production of elusive aliphatic nitriles and alkynes. All transformations described are based on a common sequence: 1) oxidative ring-opening of cyclobutanol substrates by C-C bond cleavage; 2) radical addition to triple bonds bearing an arylsulfonyl group; and 3) radical-mediated C-S bond cleavage.

Enantioselective titanium(III)-catalyzed reductive cyclization of ketonitriles

Reduction, please! The title reaction affords ?-hydroxyketones, a common structural motif in biologically active natural products, in good yields and high enantioselectivities at room temperature. The commercially available ansa-titanocene 1 was found to be an efficient catalyst for this process, which presumably proceeds by addition of a ketyl radical to a nitrile.

Direct and selective benzylic oxidation of alkylarenes via C-H abstraction using alkali metal bromides

A direct benzylic oxidation of alkylarenes via C-H bond abstraction was developed using alkali metal bromides and oxidants under mild conditions. This reaction proceeded with excellent selectivity by thermal oxidation or photooxidation to provide a broad range of carbonyl compounds containing electron-deficient aryl carbonyl compounds in high yields.