Methyl 3-oxododecanoate

Base Information

• Chemical Name: Methyl 3-oxododecanoate
• CAS No.: 76835-64-8
• Molecular Formula: C13H24 O3
• Molecular Weight: 228.332
• Hs Code.: 2918300090
• European Community (EC) Number: 278-561-8
• DSSTox Substance ID: DTXSID40998154
• Nikkaji Number: J206.342E
• Wikidata: Q82990665
• Mol file: 76835-64-8.mol

Synonyms:Methyl 3-oxododecanoate;76835-64-8;Dodecanoic acid,3-oxo-, methyl ester;EINECS 278-561-8;Dodecanoic acid, 3-oxo-, methyl ester;3-Oxolauric acid methyl ester;SCHEMBL1123527;3-oxododecanoic acid methyl ester;DTXSID40998154;FHTQHJAYSZFNSI-UHFFFAOYSA-N;BDA83564;AKOS028111684;BS-48314;E84274

Chemical Property of Methyl 3-oxododecanoate

Chemical Property:

• Vapor Pressure: 0.00634mmHg at 25°C
• Boiling Point: 271.7°C at 760 mmHg
• Flash Point: 110.4°C
• PSA: 43.37000
• Density: 0.936g/cm³
• LogP: 3.25930
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 228.17254462
• Heavy Atom Count: 16
• Complexity: 199

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-Oxododecanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC(=O)CC(=O)OC
• Uses: Methyl 3-Oxododecanoate is a useful synthetic intermediate. It is used in the tethered Biginelli reaction for enantioselective synthesis of batzelladine alkaloid.

Technology Process of Methyl 3-oxododecanoate

There total 19 articles about Methyl 3-oxododecanoate 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: 90.0%

caprinaldehyde (112-31-2) + methyl diazoacetate (6832-16-2) → methyl 3-oxododecanoate (76835-64-8)

Guidance literature:

With Cu(II)-Mont K 10 clay; In benzene; at 80 ℃; for 2h;

DOI:10.1039/a905028k

Reference yield: 82.0%

1-bromo-octane (111-83-1) + acetoacetic acid methyl ester (105-45-3) → methyl 3-oxododecanoate (76835-64-8)

Guidance literature:

acetoacetic acid methyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃;

With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.166667h;

1-bromo-octane; In tetrahydrofuran; hexane; Further stages.;

DOI:10.1021/ja011599l

Reference yield: 78.0%

monomethyl monopotassium malonate (38330-80-2) + n-decanoyl chloride (112-13-0) → methyl 3-oxododecanoate (76835-64-8)

Guidance literature:

monomethyl monopotassium malonate; With triethylamine; magnesium chloride; In acetonitrile; at 10 - 25 ℃; for 2.5h; Inert atmosphere;

n-decanoyl chloride; With triethylamine; In acetonitrile; at 0 - 25 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.01.031

upstream raw materials:

Ethyl decanoylacetoacetate

sodium methylate

methanol

3-oxo-dodecanoic acid

Downstream raw materials:

3-hydroxydodecanoic acid

methyl (R)-3-hydroxydecanoate

(S)-methyl 3-hydroxydecanoate

β-hydroxydodecanoic acid methyl ester

Refernces

• 1、 -. "COMPOUND FOR USE AGAINST PATHOGENIC NEISSERIA AND HAEMOPHILUS SPECIES AND MORAXELLA CATARRHALIS". . . Retrieved 2019/07/04.
• 2、 Szamosvári, Dávid,B?ttcher, Thomas. "An Unsaturated Quinolone N-Oxide of Pseudomonas aeruginosa Modulates Growth and Virulence of Staphylococcus aureus". supporting information. p. 7271 - 7275. Retrieved 2017/06/13.