Methyl 3-methylidene-4-oxopentanoate

Base Information

• Chemical Name: Methyl 3-methylidene-4-oxopentanoate
• CAS No.: 6277-50-5
• Molecular Formula: C7H10O3
• Molecular Weight: 142.1525
• NSC Number: 34812
• DSSTox Substance ID: DTXSID40284004
• Nikkaji Number: J693.470F
• Wikidata: Q82018786
• Mol file: 6277-50-5.mol

Synonyms:methyl 3-methylidene-4-oxopentanoate;6277-50-5;NSC34812;SCHEMBL10239632;DTXSID40284004;NSC-34812

Chemical Property of Methyl 3-methylidene-4-oxopentanoate

Chemical Property:

• Vapor Pressure: 0.0959mmHg at 25°C
• Boiling Point: 223.5°C at 760 mmHg
• Flash Point: 91.4°C
• Density: 1.018g/cm³
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 142.062994177
• Heavy Atom Count: 10
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(=C)CC(=O)OC

Technology Process of Methyl 3-methylidene-4-oxopentanoate

There total 9 articles about Methyl 3-methylidene-4-oxopentanoate 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: 78.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + methyl 3-acetyl-4-oxopentanoate (39265-95-7) → methyl 3-methylene-4-oxopentanoate (6277-50-5)

Guidance literature:

With potassium carbonate; In water; Ambient temperature;

DOI:10.1080/00397919508011455

Reference yield: 76.0%

2,5-dihydro-5-hydroxy-4,5-dimethyl-2-oxo-3-furancarboxylic acid methyl ester (60971-98-4) → methyl 3-methylene-4-oxopentanoate (6277-50-5)

Guidance literature:

at 140 ℃;

DOI:10.1021/ja00527a046

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + levulinic acid methyl ester (624-45-3) → 4-oxo-hex-5-enoic acid methyl ester (23684-13-1) + methyl 3-methylene-4-oxopentanoate (6277-50-5) + methyl 3-methylene-4-oxohex-5-enoate

Guidance literature:

With hydrogenchloride; 3-amino propanoic acid; In water; dimethyl sulfoxide; at 100 ℃; for 5h; Overall yield = 42 percent;

upstream raw materials:

2,5-dihydro-5-hydroxy-4,5-dimethyl-2-oxo-3-furancarboxylic acid methyl ester

formaldehyd

methyl 3-acetyl-4-oxopentanoate

2,5-dihydro-5-hydroxy-4,5-dimethyl-2-oxo-3-furancarboxylic acid

Downstream raw materials:

methyl 4-oxo-3-(phenylthiomethyl)pentanoate

Refernces

• 1、 Hu, Xun,Jiang, Shengjuan,Wu, Liping,Wang, Shuai,Li, Chun-Zhu. "One-pot conversion of biomass-derived xylose and furfural into levulinate esters via acid catalysis". . p. 2938 - 2941. Retrieved 2017/03/15.
• 2、 Schultz, Arthur G.,Godfrey, Jollie D.. "An Annelation Approach to the Synthesis of Eudesmane and Elemane Sesquiterpene Lactones. Total Synthesis of dl-Dihydrocallitrisin, dl-7,8-Epialantolactone, dl-7,8-Epiisoalantolactone, and dl-Atractylon". . p. 2414 - 2428. Retrieved 2007/10/02.