Methyl 5-oxooctadecanoate

Base Information

• Chemical Name: Methyl 5-oxooctadecanoate
• CAS No.: 2380-20-3
• Molecular Formula: C₁₉H₃₆O₃
• Molecular Weight: 312.493
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID80392910
• Nikkaji Number: J206.405G
• Wikidata: Q82191416
• Mol file: 2380-20-3.mol

Synonyms:Methyl 5-oxooctadecanoate;2380-20-3;5-Oxostearic acid methyl ester;methyl 5-oxostearate;Methyl 5-oxo-octadecanoate;METHYL5-OXOOCTADECANOATE;Methyl 5-oxooctadecanoate,99%;SCHEMBL8728909;Methyl 5-oxooctadecanoate, 99%;DTXSID80392910;BVRPGVKJUHZXTH-UHFFFAOYSA-N;AKOS015894366;J-015216

Chemical Property of Methyl 5-oxooctadecanoate

Chemical Property:

• Vapor Pressure: 9.31E-07mmHg at 25°C
• Melting Point: 58-60 °C(lit.)
• Refractive Index: 1.448
• Boiling Point: 404.6°C at 760 mmHg
• Flash Point: >230 °F
• PSA: 43.37000
• Density: 0.911g/cm³
• LogP: 5.59990
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 17
• Exact Mass: 312.26644501
• Heavy Atom Count: 22
• Complexity: 274

Purity/Quality:

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

Methyl 5-oxooctadecanoate 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC(=O)CCCC(=O)OC
• Uses: Methyl 5-oxooctadecanoate may be used in the synthesis of seven-, eight- and nine-membered monocyclic, bicyclic and tricyclic ring systems.

Technology Process of Methyl 5-oxooctadecanoate

There total 5 articles about Methyl 5-oxooctadecanoate 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: 67.0%

1-bromotridecane (765-09-3) + methyl 4-(chlorocarbonyl)butyrate (1501-26-4) → 5-oxostearic acid methyl ester (2380-20-3)

Guidance literature:

1-bromotridecane; With magnesium; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere; Reflux;

methyl 4-(chlorocarbonyl)butyrate; With copper(l) iodide; In tetrahydrofuran; at -78 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.bmc.2013.06.034

Reference yield:

Methyl oleate (112-62-9) → methyl 10-oxooctadecanoate (870-10-0) + methyl 8-ketooctadecanoate (2380-23-6) + 5-oxostearic acid methyl ester (2380-20-3) + methyl 9-oxooctadecanoate (1842-70-2)

Guidance literature:

With oxygen; palladium diacetate; scandium tris(trifluoromethanesulfonate); In water; acetonitrile; at 80 ℃; for 18h; under 15201 Torr; Reagent/catalyst; Solvent; Temperature; Catalytic behavior;

DOI:10.1021/acs.jafc.7b02017

Reference yield:

methyl 4-(chlorocarbonyl)butyrate (1501-26-4) → 5-oxostearic acid methyl ester (2380-20-3)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene / Behandeln des Reaktionsprodukts mit wss.-aethanol. Kalilauge

With benzene;

upstream raw materials:

5-oxo-octadecanoic acid

methyl 4-(chlorocarbonyl)butyrate

methyl 3-oxohexadecanoate

1-bromotridecane

Downstream raw materials:

methyl 4-(3-oxyl-4,4-dimethyl-2-tridecyl-1,3-oxazolidine-2-yl)butanoate

5-oxo-octadecanoic acid

N-benzyl-5-oxooctadecanamide

N-(4-chlorobenzyl)-5-oxooctadecanamide

Refernces

• 1、 Wu, Hui,Kelley, Charles J.,Pino-Figueroa, Alejandro,Vu, Huyen D.,Maher, Timothy J.. "Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition". . p. 5188 - 5197. Retrieved 2013/09/02.