Ethyl 3-oxooctanoate

Base Information

• Chemical Name: Ethyl 3-oxooctanoate
• CAS No.: 10488-95-6
• Molecular Formula: C10H18O3
• Molecular Weight: 186.251
• European Community (EC) Number: 895-310-3
• DSSTox Substance ID: DTXSID40404664
• Nikkaji Number: J132.393H
• Wikidata: Q82208950
• Mol file: 10488-95-6.mol

Synonyms:Ethyl 3-oxooctanoate;10488-95-6;3-Oxo-octanoic acid ethyl ester;caprylsaureethylester;3-Oxo-octanoicacidethylester;SCHEMBL2491946;DTXSID40404664;YGRJFGCEOYRREO-UHFFFAOYSA-N;MFCD00048873;CS-0308550;FT-0757530;EN300-124035;F79424

Chemical Property of Ethyl 3-oxooctanoate

Chemical Property:

• Boiling Point: 118-121 °C(Press: 13 Torr)
• PKA: 10.55±0.46(Predicted)
• PSA: 43.37000
• Density: 0.959±0.06 g/cm3(Predicted)
• LogP: 2.08900
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 186.125594432
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

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

Ethyl3-oxooctanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)CC(=O)OCC

Technology Process of Ethyl 3-oxooctanoate

There total 38 articles about Ethyl 3-oxooctanoate 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: 100.0%

1-bromo-butane (109-65-9) + ethyl acetoacetate (141-97-9) → ethyl 3-oxooctanoate (10488-95-6)

Guidance literature:

ethyl acetoacetate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at 0 ℃; for 1h;

1-bromo-butane; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 14h; Further stages.;

DOI:10.1055/s-2006-942536

Reference yield: 95.0%

diazoacetic acid ethyl ester (623-73-4) + hexanal (66-25-1) → ethyl 3-oxooctanoate (10488-95-6)

Guidance literature:

With molybdenium(VI) dioxodichloride; In dichloromethane; at 20 ℃; for 2.5h;

DOI:10.1055/s-2008-1067029

Reference yield: 94.0%

cycl-isopropylidene malonate (2033-24-1) + ethanol (64-17-5) + Hexanoyl chloride (142-61-0) → ethyl 3-oxooctanoate (10488-95-6)

Guidance literature:

cycl-isopropylidene malonate; Hexanoyl chloride; With pyridine; In dichloromethane; at 20 ℃; for 4.5h;

ethanol; for 7h; Heating;

DOI:10.1248/cpb.48.1567

upstream raw materials:

ethyl bromide

ethyl 3-oxo-2-acetylhexanoate

sodium ethanolate

ethanol

Downstream raw materials:

6-pentyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

3-hydroxyoctanoic acid

Ethyl 2-oxobutanoate

3-oxooctanoic acid

Refernces

• 1、 Klosa. "-". . . Retrieved 1956.
• 2、 Kanemitsu, Hironobu,Uehara, Keiji,Fukuzumi, Shunichi,Ogo, Seiji. "Isolation and crystal structures of both enol and keto tautomer intermediates in a hydration of an alkyne-carboxylic acid ester catalyzed by iridium complexes in water". . p. 17141 - 17147. Retrieved 2008.
• 3、 Jeyakumar, Kandasamy,Chand, Dillip Kumar. "Molybdenum(VI) dichloride dioxide catalyzed synthesis of β-keto esters by C-H insertion of ethyl diazoacetate into aldehydes". . p. 1685 - 1687. Retrieved 2008.
• 4、 Nguyen, Van Thi Hong,Bellur, Esen,Appel, Bettina,Langer, Peter. "Synthesis of 4-alkyl- and 4-(ω-chloroalkyl)-3-hydroxy-5- alkylidenebutenolides based on cyclizations of 4-alkyl- and 4-(ω- chloroalkyl)-1,3-bis(trimethylsilyloxy)buta-1,3-dienes with oxalyl chloride". . p. 2865 - 2872. Retrieved 2006.
• 5、 Stout,G.H.,Sears,K.D.. "-". . p. 4185 - 4190. Retrieved 1968.
• 6、 Rahaman, Mizzanoor,Ali, M. Shahnawaz,Jahan, Khorshada,Hinz, Damon,Belayet, Jawad Bin,Majinski, Ryan,Hossain, M. Mahmun. "Synthetic Scope of Br?nsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate". . p. 6138 - 6147. Retrieved 2021/05/06.
• 7、 Ortiz Zacarías, Natalia V.,Van Veldhoven, Jacobus P. D.,Den Hollander, Lisa S.,Dogan, Burak,Openy, Joseph,Hsiao, Ya-Yun,Lenselink, Eelke B.,Heitman, Laura H.,Ijzerman, Adriaan P.. "Synthesis and Pharmacological Evaluation of Triazolopyrimidinone Derivatives as Noncompetitive, Intracellular Antagonists for CC Chemokine Receptors 2 and 5". . p. 11035 - 11053. Retrieved 2019/12/24.