Ethyl 5-oxohexanoate

Base Information

• Chemical Name: Ethyl 5-oxohexanoate
• CAS No.: 13984-57-1
• Molecular Formula: C8H14 O3
• Molecular Weight: 158.197
• Hs Code.: 2918300090
• European Community (EC) Number: 237-776-7
• UNII: DJ9EME6QBQ
• DSSTox Substance ID: DTXSID6065688
• Nikkaji Number: J129.278A
• Wikidata: Q81992325
• Mol file: 13984-57-1.mol

Synonyms:Ethyl 5-oxohexanoate;Ethyl 4-acetylbutyrate;13984-57-1;Hexanoic acid, 5-oxo-, ethyl ester;5-Oxohexanoic acid ethyl ester;DJ9EME6QBQ;EINECS 237-776-7;MFCD00009213;Ethyl 4-acetylbutanoate;UNII-DJ9EME6QBQ;ethyl 4-acetyl-butanoate;ETHYL4-ACETYLBUTYRATE;SCHEMBL723390;Ethyl 4-acetylbutyrate, 98%;5-oxo-hexanoic acid ethyl ester;DTXSID6065688;MGPSIDGTLFKDEY-UHFFFAOYSA-;BBL027744;STL373437;AKOS015915557;CS-W010896;AS-44005;SY033235;FT-0626069;EN300-105271;A885944;J-800372;BKN

Chemical Property of Ethyl 5-oxohexanoate

Chemical Property:

• Vapor Pressure: 0.103mmHg at 25°C
• Refractive Index: n20/D 1.427(lit.)
• Boiling Point: 222.1°Cat760mmHg
• Flash Point: 69.4°C
• PSA: 43.37000
• Density: 0.981g/cm³
• LogP: 1.30880
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 140

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-OxohexanoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CCCC(=O)C
• Uses: 5-Oxohexanoic Acid Ethyl Ester is a useful synthetic intermediate. It is used to prepare tyrosine-derived RGD peptidomimetics containing oligoethylene glycol (OEG) spacers. It is also used to synthesize constrained glycyl amides derived from RGD tripeptide as nonpeptide αvβ3 antagonists.

Technology Process of Ethyl 5-oxohexanoate

There total 25 articles about Ethyl 5-oxohexanoate 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: 94.0%

5-hydroxy-hex-2-enoic acid ethyl ester (75958-92-8) → ethyl 5-oxohexanoate (13984-57-1)

Guidance literature:

With [Pd(dtbpe)MeCl]; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; cyclohexene; In 1,2-dichloro-ethane; at 120 ℃; for 18h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;

DOI:10.1021/jacs.6b06390

Reference yield: 93.0%

methyl vinyl ketone (78-94-4,25038-87-3) + 1-ethoxyacetylene (927-80-0) → ethyl 5-oxohexanoate (13984-57-1)

Guidance literature:

With 9-iodo-9-borabicyclo{3.3.1}nonane; In pentane; at -78 - 25 ℃; for 2.5h; Mechanism; further reactants, further products;

Reference yield: 80.0%

ethyl glutaroyl chloride (5205-39-0) + methylmagnesium bromide (75-16-1) → ethyl 5-oxohexanoate (13984-57-1)

Guidance literature:

methylmagnesium bromide; With tributylphosphine; In tetrahydrofuran; at 20 ℃;

ethyl glutaroyl chloride; In tetrahydrofuran; at -40 ℃; for 0.333333h;

DOI:10.1248/cpb.48.1196

upstream raw materials:

diethyl 2-acetylglutarate

ethanol

ethyl 2-(2-cyanoethyl)-3-oxobutanoate

2-acetyl-glutaric acid-5-ethyl ester-1-tert-butyl ester

Downstream raw materials:

1,3-cylohexanedione

(+/-)-5-hydroxy-5-phenyl-hexanoic acid

Ethyl 5-hydroxyhexanoate

hexane-1,5-diol

Refernces

• 1、 Fernandes,Rocha,Mai,Mota, Claudio J.A.,Teixeira Da Silva. "Levulinic acid esterification with ethanol to ethyl levulinate production over solid acid catalysts". . p. 199 - 204. Retrieved 2012.
• 2、 Kulkarni,Sebastian. "An efficient synthesis of τ/δ keto esters". . p. 581 - 586. Retrieved 1991.
• 3、 Bennett, Elliot L.,Brookfield, Adam,Guan, Renpeng,Huang, Zhiliang,Mcinnes, Eric J. L.,Robertson, Craig M.,Shanmugam, Muralidharan,Xiao, Jianliang. "Oxidative Cleavage of Alkenes by O2with a Non-Heme Manganese Catalyst". supporting information. p. 10005 - 10013. Retrieved 2021/07/19.
• 4、 Fernandes, Rodney A.,Ramakrishna, Gujjula V.,Bethi, Venkati. "MnO2as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins". . p. 6115 - 6125. Retrieved 2020/10/27.