1501-05-9

Usage

Uses

Used in Organic Synthesis:
4-Benzoylbutyric acid is used as a key intermediate for the synthesis of various organic compounds, contributing to the development of new chemical entities and materials.
Used in Pharmaceutical Industry:
4-Benzoylbutyric acid is utilized as a building block in the production of pharmaceuticals, playing a crucial role in the development of new drugs and medications.
Used in Agrochemicals:
4-Benzoylbutyric acid is employed as a vital component in the formulation of agrochemicals, such as pesticides and fertilizers, to enhance crop protection and yield.
Used in Dyestuff Industry:
4-Benzoylbutyric acid is used as a starting material for the production of dyes and pigments, contributing to the creation of vibrant colors and shades in various applications.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 5273, 1951 DOI: 10.1021/ja01155a078

Upstream product

• 5205-39-0 ethyl glutaroyl chloride 
• 108-55-4 glutaric anhydride, 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 34502-63-1 6-Phenyl-1,2,3,4-tetrahydropyridin-2-on 
• 57-57-8 β-Propiolactone 
• 93-91-4 1-phenylbutan-1,3-dione 
• 100388-04-3 2-(3-bromo-propyl)-2-phenyl-[1,3]dioxolane 
• 10487-96-4 1-phenylcyclopentanol 
• 825-54-7 cyclopent-1-en-1-ylbenzene 
• 3350-92-3 5-phenylpent-4-ynoic acid 
• 75424-63-4 5-oxo-5-phenylpentanal 
• 322764-79-4 5-hydroxy-5-phenyl-valeraldehyde 
• 64-19-7 acetic acid 

Downstream Products

• 1501-04-8 Methyl 4-benzoylbutanoate 
• 73172-56-2 ethyl 4-benzoylbutanoate 
• 34502-63-1 6-Phenyl-1,2,3,4-tetrahydropyridin-2-on 
• 10413-17-9 6-phenyltetrahydropyran-2-one 
• 2270-20-4 5-Phenylpentanoic acid 
• 14293-04-0 5-hydroxyimino-5-phenylpentanoic acid 
• 39826-14-7 4-bromo-5-oxo-5-phenyl-pentanoic acid 
• 7088-09-7 8a-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 
• 30788-21-7 3.7-Diketo-2-methyl-7-phenyl-heptansaeure-ethylester 
• 61797-68-0 5-Oxo-5-phenyl-pentanoic acid cyclohexyl-{2-[cyclohexyl-(5-oxo-5-phenyl-pentanoyl)-amino]-ethyl}-amide 
• 2952-86-5 8a-phenyl-hexahydro-thiazolo[3,2-a]pyridin-5-one 
• 7088-10-0 9a-phenyl-hexahydro-pyrido[2,1-b][1,3]oxazin-6-one 
• 90991-26-7 5-(3-nitrophenyl)-5-oxopentanoic acid 
• 91247-40-4 5-amino-5-phenylpentanoic acid 

Relevant academic research and scientific papers

The [2+2] photocycloaddition of uracil derivatives with ethylene as a general route to cis-cyclobutane β-amino acids

A three-step procedure, based on the [2+2]-photochemical reaction of uracils with ethylene followed by controlled degradation of the heterocyclic ring, has been developed for the synthesis of a range of C1 - and C2-substituted cis-cyclobutane β-amino acids, in good overall yield. Georg Thieme Verlag Stuttgart.

Ultrasound-promoted Friedel-Crafts acylation of arenes and cyclic anhydrides catalyzed by ionic liquid of [bmim]Br/AlCl3

A simple and efficient method of Friedel-Crafts acylation of arenes with succinic anhydride, phthalic anhydride and glutaric anhydride under the action of 1-butyl-3-ethylimidazolium ([bmim]Br/AlCl3 ([bmim]+) cation (ionic liquid) and ultrasound irradiation is presented. Thy purity of products was tested by GC-MS and their structures evaluated by IR and 1H NMR spectroscopy.

A general and versatile synthesis of 4- and 5-oxoacids

The condensation of Grignard reagents with succinic or glutaric anhydrides in presence of a catalytic amount of CuI is a good way for the preparation of 4- or 5-oxoacids.

Three-component, one-pot synthesis of benzo[6,7]cyclohepta[1,2-b]pyridine derivatives under catalyst free conditions and evaluation of their anti-inflammatory activity

An efficient three-component protocol is described for the synthesis of benzo[6,7]cyclohepta[1,2-b]pyridine derivatives using β-chloroacroleins, 1,3-dicarbonyls and ammonium acetate under catalyst free conditions by using ethanol as reaction media. The mild reaction conditions, operational simplicity and high yields are the advantages of this protocol and the broad scope of this one-pot reaction makes this procedure promising for practical usages. All the final compounds were screened for anti-inflammatory activity. Among the compounds tested, the compounds 5a, 5b, 5c, 5d, 5f, and 5k exhibited significant inhibition of IL-1β and MCP-1 secretion as a measure of anti-inflammatory activity.

Design, synthesis and in vitro anti-tuberculosis activity of benzo[6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole derivatives

A series of novel benzo[6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole hybrids (7a–j & 8a–j) have been designed and synthesized in excellent yields by Huisgen's [3+2] cyclo addition reaction of 3-(azidomethyl)-2-methyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine (5) with various alkynes 6 in presence of copper sulphate and sodium ascorbate and their structures were confirmed by IR, 1H NMR, 13C NMR and HRMS. The newly synthesized compounds 7a–j & 8a–j were evaluated for their in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC 27294). Among the compounds tested, the compounds 7i and 8g displayed most potent activity with MIC value of 1.56 μg/mL with low cytotoxicity.

Visible Light-Driven, Copper-Catalyzed Aerobic Oxidative Cleavage of Cycloalkanones

A visible light-driven, copper-catalyzed aerobic oxidative cleavage of cycloalkanones has been presented. A variety of cycloalkanones with varying ring sizes and various α-substituents reacted well to give the distal keto acids or dicarboxylic acids with moderate to good yields.

Nitroxyl Catalysts for Six-Membered Ring Bromolactonization and Intermolecular Bromoesterification of Alkenes with Carboxylic Acids

We developed a nitroxyl-catalyzed bromoesterification of alkenes with bromo reagents, which includes a six-membered ring bromolactonization of alkenyl carboxylic acids catalyzed by AZADO as the nitroxyl radical catalyst, and an intermolecular bromoesterification of alkenes with carboxylic acids using NMO as the N-oxide catalyst. We also accomplished a remote diastereoselective bromohydroxylation via an AZADO-catalyzed six-membered ring bromolactonization and a subsequent ring cleavage reaction with alkylamines to furnish ?-bromo-δ-hydroxy amides with high diastereoselectivity.

Iridium-Catalyzed Asymmetric Hydrogenation of ?- A nd ?-Ketoacids for Enantioselective Synthesis of ?- A nd ?-Lactones

A highly efficient asymmetric hydrogenation of ?- A nd ?-ketoacids was developed by using a chiral spiro iridium catalyst (S)-1a, affording the optically active ?- A nd ?-hydroxy acids/lactones in high yields with excellent enantioselectivities (up to >99% ee) and turnover numbers (TON up to 100000). This protocol provides an efficient and practical method for enantioselective synthesis of Ezetimibe.

Asymmetric hydrogenation reaction γ - or δ - ketonato compound (by machine translation)

The invention relates to the field, of organic chemistry, specifically γ - or δ - keto acid compound asymmetric hydrogenation reaction, reaction formula as follows : Wherein R is H,C. 1 - C6 An alkyl or halogen, is R 1 - 5 in number of substituents . wherein n is 1 or 2;Cat. is a chiral spiro pyrimidyl phosphine ligand iridium complex . and γ - or δ - keto acid compound is subjected to an internal esterification reaction to further prepare a lactone compound. (by machine translation)

Design, synthesis, and evaluation of compounds capable of reducing Pseudomonas aeruginosa virulence

Anti-virulence approaches in the treatment of Pseudomonas aeruginosa (PA)-induced infections have shown clinical potential in multiple in vitro and in vivo studies. However, development of these compounds is limited by several factors, including the lack of molecules capable of penetrating the membrane of gram-negative organisms. Here, we report the identification of novel structurally diverse compounds that inhibit PqsR and LasR-based signaling and diminish virulence factor production and biofilm growth in two clinically relevant strains of P. aeruginosa. It is the first report where potential anti-virulent agents were evaluated for inhibition of several virulence factors of PA. Finally, co-treatment with these inhibitors significantly reduced the production of virulence factors induced by the presence of sub-inhibitory levels of ciprofloxacin. Further, we have analyzed the drug-likeness profile of designed compounds using quantitative estimates of drug-likeness (QED) and confirmed their potential as hit molecules for further development.