Methyl 2-acetyl-5-oxohexanoate

Base Information

• Chemical Name: Methyl 2-acetyl-5-oxohexanoate
• CAS No.: 35490-04-1
• Molecular Formula: C9H14 O4
• Molecular Weight: 186.208
• Hs Code.: 2918300090
• European Community (EC) Number: 252-592-7
• DSSTox Substance ID: DTXSID40956895
• Nikkaji Number: J260.634H
• Mol file: 35490-04-1.mol

Synonyms:Methyl 2-acetyl-5-oxohexanoate;35490-04-1;EINECS 252-592-7;SCHEMBL3752221;DTXSID40956895;AKOS006328340;2-Acetyl-5-oxohexanoic acid methyl ester

Chemical Property of Methyl 2-acetyl-5-oxohexanoate

Chemical Property:

• Vapor Pressure: 0.00237mmHg at 25°C
• Boiling Point: 288.2°Cat760mmHg
• Flash Point: 124.4°C
• PSA: 60.44000
• Density: 1.062g/cm³
• LogP: 0.73380
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 186.08920892
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

98%Min ^*data from raw suppliers

2-Acetyl-5-oxo-hexanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CCC(C(=O)C)C(=O)OC
• Uses: 2-Acetyl-5-oxo-hexanoic Acid Methyl Ester is an intermediate in the synthesis of Methyl 5-Methyl-1-(1-phenylpropan-2-yl)-1H-pyrrole-2-carboxylate (M338390), which is an impurity of the drug Amphetamine (A634248).

Technology Process of Methyl 2-acetyl-5-oxohexanoate

There total 2 articles about Methyl 2-acetyl-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: 98.0%

2-hydroxy-3-butene (598-32-3) + acetoacetic acid methyl ester (105-45-3) → 2-acetyl-5-oxo-hexanoic acid methyl ester (35490-04-1)

Guidance literature:

With oxygen; In tetrahydrofuran; at 30 ℃; for 20h; under 760.051 Torr;

DOI:10.1021/ja110142y

Reference yield: 95.0%

methyl vinyl ketone (78-94-4,25038-87-3) + acetoacetic acid methyl ester (105-45-3) → 2-acetyl-5-oxo-hexanoic acid methyl ester (35490-04-1)

Guidance literature:

bis(acetylacetonate)nickel(II); at 40 ℃; for 48h;

DOI:10.1021/jo051192p

Reference yield: 85.0%

nitrostyrene (5153-67-3) + 2-acetyl-5-oxo-hexanoic acid methyl ester (35490-04-1) → methyl (1R,2R,3S,4R)-1-acetyl-4-hydroxy-4-methyl-3-nitro-2-phenyl-cyclohexanecarboxylate (1033363-22-2)

Guidance literature:

With (R)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanamine; In diethyl ether; at 23 ℃; for 16h; optical yield given as %ee; stereoselective reaction;

DOI:10.1021/ol8007183

upstream raw materials:

methyl vinyl ketone

acetoacetic acid methyl ester

2-hydroxy-3-butene

Downstream raw materials:

4-Methyl-2-oxo-cyclohex-3-enecarboxylic acid methyl ester

methyl 2-methyl-4-oxocyclohex-2-enecarboxylate

(3S,8aR)-5,8a-dimethyl-3-phenyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridine-6-carboxylic acid methyl ester

methyl (1R,2R,3S,4R)-1-acetyl-4-hydroxy-4-methyl-3-nitro-2-phenyl-cyclohexanecarboxylate

Refernces

• 1、 Bittner, Bozena,Koppe, Karsten,Frank, Walter,Ignat'Ev, Nikolai. "Michael addition catalyzed by difluorotris(pentafluoroethyl)phosphorane". supporting information. p. 22 - 27. Retrieved 2015/12/30.
• 2、 Mekonnen, Alemayehu,Carlson, Rolf. "Lewis acid catalyzed conjugate addition and the formation of heterocycles using Michael acceptors under solvent-free conditions". . p. 2005 - 2013. Retrieved 2007/10/03.