Ethyl 5-oxopentanoate

Base Information

• Chemical Name: Ethyl 5-oxopentanoate
• CAS No.: 22668-36-6
• Molecular Formula: C7H12O3
• Molecular Weight: 144.17
• DSSTox Substance ID: DTXSID30456475
• Nikkaji Number: J1.311.178B
• Wikidata: Q82278988
• Mol file: 22668-36-6.mol

Synonyms:ethyl 5-oxopentanoate;22668-36-6;Pentanoic acid, 5-oxo-, ethyl ester;5-oxoPentanoic acid ethyl ester;4-carbethoxybutanal;SCHEMBL3964566;Pentanoicacid,5-oxo-,ethylester;5-oxo-pentanoic acid ethyl ester;DTXSID30456475;WUPBOSISFPJABC-UHFFFAOYSA-N;MFCD12025145;AM85359;FT-0696256;EN300-97497;N10598

Chemical Property of Ethyl 5-oxopentanoate

Chemical Property:

• PSA: 43.37000
• Density: 0.995g/ml
• LogP: 0.91870
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 144.078644241
• Heavy Atom Count: 10
• Complexity: 109

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CCCC=O

Technology Process of Ethyl 5-oxopentanoate

There total 18 articles about Ethyl 5-oxopentanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-<(Naphthalen-2-ylthio)carbonyl>butylcarboxylic acid ethyl ester → ethyl 5-oxopentanoate (22668-36-6)

Guidance literature:

With cyclohexa-1,4-diene; In benzene; for 110h; Irradiation;

DOI:10.1021/jo00088a053

Reference yield: 82.0%

ethyl-δ-hydroxyvalerate (13107-53-4) → ethyl 5-oxopentanoate (22668-36-6)

Guidance literature:

ethyl-δ-hydroxyvalerate; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 21 ℃; for 1h; Inert atmosphere;

DOI:10.1039/c7ob02406a

Reference yield: 72.0%

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → ethyl 5-oxopentanoate (22668-36-6)

Guidance literature:

With sulfuric acid; sodium hydrogencarbonate; pyridinium chlorochromate; In ethanol; dichloromethane; pentane;

upstream raw materials:

ethyl glutaroyl chloride

1,3-Dioxolan-2-buttersaeure-ethylester

ethyl 3-butenoate

carbon monoxide

Downstream raw materials:

ethyl 7-oxo-6-phenylthio-5-octenoate

(3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine

(3R,8aR)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

(3S,8aR)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Refernces

The total synthesis of antrimycin D(v); II: Synthesis of tetrahydropyridazinecarboxylic acid and its incorporation into peptides

10.1055/s-1993-25947

The study focuses on the synthesis of tetrahydropyridazinecarboxylic acid and its integration into peptides. The researchers used various chemicals, including di- and tripeptides containing (R, S)-tetrahydropyridazine-3-carboxylic acids, which were synthesized via protected y-formyl-a-hydrazinobutyric acids. These acids were obtained from acetals of ethyl 7-formylbutyrate or ethyl y-formyl-α-oxobutyrate. The study also involved the synthesis of non-proteinogenic amino acids such as (hydroxymethyl)serine, dehydrovaline, dehydroisoleucine, (S,S)-α,β-diaminobutyric acid, and (S)-tetrahydropyridazinecarboxylic acid. The researchers explored two approaches to synthesize tetrahydropyridazinecarboxylic acid, one involving the reduction of tert-butoxycarbonyl-hydrazones and the other using the acetal of ethyl 5-oxopentanoate. The study aimed to overcome difficulties encountered in the synthesis of peptides containing tetrahydropyridazinecarboxylic acid and to provide detailed experimental procedures for the synthesis of antrimycin D.