26516-27-8

Basic information

• Product Name: pentanoic acid,3-methyl-2-oxo-,ethyl ester
• Synonyms: Pentanoic acid, 3-methyl-2-oxo-, ethyl ester;pentanoic acid,3-methyl-2-oxo-,ethyl ester
• CAS NO: 26516-27-8
• Molecular Formula: C8H14 O3
• Molecular Weight: 158.2
• Mol File: 26516-27-8.mol

Chemical Properties

• Boiling Point: 205.2°C at 760 mmHg
• Flash Point: 77.1°C
• Appearance: /
• Density: 0.979g/cm³
• Vapor Pressure: 0.253mmHg at 25°C
• Refractive Index: 1.419
• Solubility: Dichloromethane; Diethyl ether
• CAS DataBase Reference: pentanoic acid,3-methyl-2-oxo-,ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: pentanoic acid,3-methyl-2-oxo-,ethyl ester(26516-27-8)
• EPA Substance Registry System: pentanoic acid,3-methyl-2-oxo-,ethyl ester(26516-27-8)

Safety Data

• Hazardous Substances Data: 26516-27-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Pentanoic acid, 3-methyl-2-oxo-, ethyl ester is used as an intermediate in the synthesis of 3-methyl-2-oxovaleric acid sodium salt (M326420) for its potential therapeutic applications. pentanoic acid,3-methyl-2-oxo-,ethyl ester is an α-ketomonocarboxylic acid that has the ability to trigger insulin release by acting upon receptor sites that are distinct from those occupied by amino acids, making it a valuable component in the development of treatments for diabetes and other related conditions.
Used in Chemical Synthesis:
In the chemical industry, pentanoic acid, 3-methyl-2-oxo-, ethyl ester is utilized as a key intermediate in the synthesis of various organic compounds, including 4-methyl-2-oxovaleric acid, which is an analogue of the essential amino acid isoleucine. This ester's reactivity and functional group make it a versatile building block for creating a wide range of molecules with diverse applications in different industries.

InChI:InChI=1/C8H14O3/c1-4-6(3)7(9)8(10)11-5-2/h6H,4-5H2,1-3H3

Upstream product

• 78-76-2 s-butyl bromide 
• 95-92-1 oxalic acid diethyl ester 
• 201230-82-2 carbon monoxide 
• 920-36-5 (2-methylpropyl)lithium 
• 105-58-8 Diethyl carbonate 
• 87921-33-3 C₄H₉BrCd 
• 623-49-4 ethyl cyanoformate 
• 857975-91-8 ethyl 3-(2-mewthoxyethyl)-3-methylglycidate 
• 671795-46-3 sec-butylmagnesium bromide 

Downstream Products

• 1460-34-0 2-oxo-3(RS)-methylvaleric acid 

Relevant articles and documents

Biocatalytic Construction of Quaternary Centers by Aldol Addition of 3,3-Disubstituted 2-Oxoacid Derivatives to Aldehydes

The congested nature of quaternary carbons hinders their preparation, most notably when stereocontrol is required. Here we report a biocatalytic method for the creation of quaternary carbon centers with broad substrate scope, leading to different compound classes bearing this structural feature. The key step comprises the aldol addition of 3,3-disubstituted 2-oxoacids to aldehydes catalyzed by metal dependent 3-methyl-2-oxobutanoate hydroxymethyltransferase from E. coli (KPHMT) and variants thereof. The 3,3,3-trisubstituted 2-oxoacids thus produced were converted into 2-oxolactones and 3-hydroxy acids and directly to ulosonic acid derivatives, all bearing gem-dialkyl, gem-cycloalkyl, and spirocyclic quaternary centers. In addition, some of these reactions use a single enantiomer from racemic nucleophiles to afford stereopure quaternary carbons. The notable substrate tolerance and stereocontrol of these enzymes are indicative of their potential for the synthesis of structurally intricate molecules.

Synthesis of α-Diketones by Direct, Low-temperature, in Situ Nucleophilic Acylation of Esters by Acyllithium Reagents

Addition of n-, sec-, or tert-butyllithium to a CO-saturated solution of an ester, R'CO2R'' in a solvent system of 4:4:1 (by volume) THF/Et2O/pentane at -110 deg C (or at -135 deg C in 3:1 (by volume) Me2O/THF), followed by hydrolysis with saturated aqueous NH4Cl, results in the formation of α-diketones, BuC(O)C(O)R', yellow liquids, in good yield.Similar reactions with diethyl succinate gave in one instance both t-BuC(O)C(O)CH2CH2CO2Et and t-BuC(O)C(O)CH2CH2C(O)C(O)Bu-t.The monoacylation product of dimethyl oxalate, t-BuC(O)C(O)CO2Me, readily formed a crystalline hydrate, t-BuC(O)C(OH)2CO2Me.

Studies on Conjugated Nitriles. IV. Reaction of Ethyl Cyanoformate with Organomagnesium, -zinc, and - cadmium Reagents, and Phosphonium Ylide

The reaction of ethyl cyanoformate (1a) with phenylcadmium bromide (3a) gave ethyl benzoate (4), ethyl 2-phenyl-2-oxoacetate (5a), and 2-ethoxycarbonyl-2,4-diphenyl-3-imidazoline-5-one (6).In the presence of zinc chloride, the addition of 3a to the cyano group of 1a occured to give only 5a.The similar reaction of 1a with other organocadmium reagents (3b-f) in the presence of zinc chloride gave the corresponding α-ketoesters (5b-f) in moderate yields.The reactions of 1a with other organometallic reagents, e.g. phenylmagnesium (2a), -zinc (8) and -mercuric bromide (9) in the presence or in the absence of zinc chloride were examined.Furthermore, the addition of phosphonium ylide 13a to the cyano group of 1a in the presence of stannic chloride occured exclusively to give the phosphonium salt 14.The results are discussed in terms of the hard and soft acids and bases (HSAB) principle.Keywords - ethyl cyanoformate; benzoyl cyanide; organocadmium reagent; organozinc reagent; phosphonium ylide; cyano group addition; α-ketoester; α-dehydroamino ester; Lewis acid

Synthesis of piperazine-2,5-diones related to bicyclomycin: 1,4-dibenzyl-3-hydroxy-3-piperazine-2,5-dione. 2. Route via cyclic intermediates

1,4-Dibenzyl-3-hydroxy-3-piperazine-2,5-dione (43),which incorporates several of the structural features of the antibiotic bicyclomycin, has been synthesized via a reaction sequence involving early construction of the piperazine-2,5-dione ring.In model studies 3-isopropylidenepiperazine-2,5-dione was di-N-benzylated and epoxidized to give 4,7-dibenzyl-2,2-dimethyl-1-oxa-4,7-diazaspirooctane-5,8-dione (10).The opening of the epoxide ring of 10 by several reagents was investigated and it was found that treatment with magnesium isopropylcyclohexylamide (MICA) gives 1,4-dibenzyl-3-hydroxy-3-(1-methylethenyl)piperazine-2,5-dione (23).Treatment of ethyl 3-(2-methoxyethyl)-3-methyl-glycidate (28) with p-toluenesulfonic acid followed by hydrogenation and oxidation gives ethyl 5-methoxy-3-methyl-2-oxopentanoate, which on reaction with chloroacetamide and sulfuric acid followed by treatment of the resulting enamide with ammonia gives (Z)- and (E)-3-(4-methoxybut-2-ylidene)piperazine-2,5-dione.Di-N-benzylation of these followed by epoxidation gives (Z)- and (E)-4,7-dibenzyl-2-(2-methoxyethyl)-2-methyl-1-oxa-4,7-diazaspirooctane-5,8-dione (41 and 42).Treatment of 41 with MICA converts it to compound 43.Chromatography of 43 on silica converts it in part to N-benzyl-N-(2-benzylamino-2-oxoethyl)-3-(2-methoxyethyl)-2-oxo-3-butenamide, which on treatment with MICA regenerates 43.

Approaches to the Synthesis of Bicyclomycin

3-Acetoxy-1,4-dibenzyl-3-(3-methoxy-1-methylenepropyl)piperazine-2,5-dione (4) has been synthesized both via cyclization of N-benzyl-N-(N-benzylcarbamoylmethyl)-5-methoxy-3-methylene-2-oxopentanamide (10) and via cleavage of the epoxide ring of 4,7-dibenz