15118-53-3

Usage

Uses

Used in Pharmaceutical Industry:
2,2-Dimethyl-4-oxohexanoic acid is utilized as a key intermediate in the synthesis of various drugs and organic chemicals. Its unique chemical properties, including the presence of both carboxylic acid and ketone functional groups, make it an essential component in the development of new pharmaceutical compounds.
Used in Chemical Industry:
In the chemical industry, 2,2-Dimethyl-4-oxohexanoic acid is employed as a versatile building block for the synthesis of a wide range of organic compounds. Its ability to participate in various chemical reactions, such as esterification, amidation, and reduction, allows for the creation of diverse chemical products with different applications.
Used in Synthesis of Fragrances and Flavors:
2,2-Dimethyl-4-oxohexanoic acid is also used as a starting material in the production of fragrances and flavors. Its ability to undergo various chemical transformations enables the creation of unique scent and taste profiles, contributing to the development of novel products in the fragrance and flavor industries.
Used in Research and Development:
Due to its reactivity and functional group diversity, 2,2-Dimethyl-4-oxohexanoic acid is frequently employed in research and development settings. It serves as a model compound for studying various chemical reactions and mechanisms, as well as a precursor for the synthesis of new compounds with potential applications in various fields.

Upstream product

• 89509-76-2 ethyl 2,2-dimethyl-4-oxohexanoate 
• 14307-98-3 5-ethyl-2,2-dimethoxy-3,3-dimethyl-2,3-dihydro-furan 
• 54491-23-5 2,2-dimethyl-4-hydroxyhexanoic acid γ-lactone 
• 17347-61-4 2,2-dimethylsuccinic anhydride 
• 557-20-0 diethylzinc 
• 597-43-3 2,2-dimethylsuccinic acid 

Downstream Products

• 125687-09-4 2,2-Dimethyl-3-(3-methyl-1H-indol-2-yl)-propionic acid 
• 42365-43-5 (4-chlorophenyl)methanamine hydrochloride 
• 125687-06-1 3-(1-(4-chlorobenzyl)-3-methyl-1H-indol-2-yl)-2,2-dimethylpropanoic acid 
• 125687-12-9 4-[(4-Chloro-benzyl)-(4-fluoro-phenyl)-hydrazono]-2,2-dimethyl-hexanoic acid 
• 125687-11-8 C₁₄H₁₃⁽²⁾H₄NO₂ 
• 125687-08-3 C₂₁H₁₈⁽²⁾H₄ClNO₂ 
• 103253-35-6 3-[1-(4-chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid 
• 1427215-02-8 C₂₂H₂₂ClNO₄ 
• 103253-15-2 3-[1-(4-chlorophenylmethyl)-5-fluoro-3-methylindol-2-yl]-2,2-dimethylpropanoic acid 
• 125687-07-2 3-[1-(4-Chloro-benzyl)-3-methyl-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester 
• 862555-24-6 3-[1-(4-chloro-benzyl)-5-(2-fluoro-2'-methyl-biphenyl-4-yl)-3-methyl-1H-indol-2-yl]-2,2-dimethyl-propionic acid methyl ester 

Relevant academic research and scientific papers

Development of potent and selective indomethacin analogues for the inhibition of AKR1C3 (type 5 17β-hydroxysteroid dehydrogenase/prostaglandin F synthase) in castrate-resistant prostate cancer

Castrate-resistant prostate cancer (CRPC) is a fatal, metastatic form of prostate cancer. CRPC is characterized by reactivation of the androgen axis due to changes in androgen receptor signaling and/or adaptive intratumoral androgen biosynthesis. AKR1C3 is upregulated in CRPC where it catalyzes the formation of potent androgens. This makes AKR1C3 a target for the treatment of CRPC. AKR1C3 inhibitors should not inhibit AKR1C1/AKR1C2, which inactivate 5α-dihydrotestosterone. Indomethacin, used to inhibit cyclooxygenase, also inhibits AKR1C3 and displays selectivity over AKR1C1/AKR1C2. Parallel synthetic strategies were used to generate libraries of indomethacin analogues, which exhibit reduced cyclooxygenase inhibitory activity but retain AKR1C3 inhibitory potency and selectivity. The lead compounds inhibited AKR1C3 with nanomolar potency, displayed >100-fold selectivity over AKR1C1/AKR1C2, and blocked testosterone formation in LNCaP-AKR1C3 cells. The AKR1C3·NADP +·2′-des-methyl-indomethacin crystal structure was determined, and it revealed a unique inhibitor binding mode. The compounds reported are promising agents for the development of therapeutics for CRPC.

Highly efficient nickel-catalyzed cross-coupling of succinic and glutaric anhydrides with organozinc reagents

A nickel-catalyzed alkylation of succinic and glutaric anhydrides with alkyl- and arylzinc reagents has been developed. A dramatic olefin effect has been investigated resulting in the identification of several styrene-based promoters which show pronounced enhancements in reaction rate. The substrate scope with respect to electrophilic and nucleophilic coupling partners has been examined and found to be remarkably broad, allowing for rapid introduction of molecular complexity through the use of functionalized coupling partners. Regioselective alkylation of an unsymmetrical succinic anhydride and a profound effect of pendent coordinating olefins on reaction rate suggest a mechanism involving discrete oxidative addition of the nickel complex into the cyclic anhydride followed by a transmetalation event.

An Unusual Fischer Indole Synthesis with 4-Keto Acids: An Indole Incorporating the Terminal Hydrazine Nitrogen

During preparation of a pharmaceutically active, N-benzylated indole derivative from 4-keto acid and N1-benzylated phenylhydrazine precursors, the N-unsubstituted indole analogue arose as a significant byproduct.The proportion of debenzylated indole was greater with α-alkylated rather than straight-chain keto acids and the byproduct was fully suppressed when a keto ester was substituted for the keto acid.The benzylic group was shown to have eliminated as the amine and 15N label incorporation demonstrated terminal phenylhydrazine nitrogen incorporation in the indole byproduct only, an exception to the usual course of the Fischer indolization reaction.A ring-chain equilibration in the ketimino acid intermediate is proposed to account for the competing pathway.