Methyl 3-oxohept-6-ynoate

Base Information

• Chemical Name: Methyl 3-oxohept-6-ynoate
• CAS No.: 100330-50-5
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• DSSTox Substance ID: DTXSID50438470
• Nikkaji Number: J731.272E
• Wikidata: Q82254224
• Mol file: 100330-50-5.mol

Synonyms:Methyl 3-oxohept-6-ynoate;100330-50-5;6-Heptynoic acid, 3-oxo-, methyl ester;Methyl 3-Oxo-6-heptynoate;Methyl3-oxohept-6-ynoate;SCHEMBL12561231;DTXSID50438470;BCP18059;3-Oxo-6-heptynoic acid methyl ester;MFCD24688654;AS-63834;SY103833;CS-0038476;FT-0726590;EN300-333538;N11412

Chemical Property of Methyl 3-oxohept-6-ynoate

Chemical Property:

• Boiling Point: 231.1±15.0 °C(Predicted)
• PKA: 10.27±0.46(Predicted)
• PSA: 43.37000
• Density: 1.063±0.06 g/cm3(Predicted)
• LogP: 0.53200
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 197

Purity/Quality:

99%, ^*data from raw suppliers

Methyl 3-oxohept-6-ynoate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(=O)CCC#C

Technology Process of Methyl 3-oxohept-6-ynoate

There total 6 articles about Methyl 3-oxohept-6-ynoate 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: 82.0%

4-pentynoic acid (6089-09-4) + monomethyl monopotassium malonate (38330-80-2) → 3-oxo-hept-6-ynoic acid methyl ester (100330-50-5)

Guidance literature:

monomethyl monopotassium malonate; With magnesium chloride; In tetrahydrofuran; at 50 ℃; for 4h;

4-pentynoic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 5 - 20 ℃; for 1h;

DOI:10.1055/s-0031-1291145

Reference yield: 76.0%

acetoacetic acid methyl ester (105-45-3) + propargyl bromide (106-96-7) → 3-oxo-hept-6-ynoic acid methyl ester (100330-50-5)

Guidance literature:

acetoacetic acid methyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.166667h; Inert atmosphere;

With n-butyllithium; In tetrahydrofuran; for 0.5h; Inert atmosphere; Cooling;

propargyl bromide; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere; Cooling;

DOI:10.1039/C7CC00103G

Reference yield: 56.0%

3-Bromo-but-1-yne (113647-42-0,18668-72-9) + acetoacetic acid methyl ester (105-45-3) → 3-oxo-hept-6-ynoic acid methyl ester (100330-50-5)

Guidance literature:

acetoacetic acid methyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.166667h; Inert atmosphere;

With n-butyllithium; In tetrahydrofuran; for 0.5h; Inert atmosphere; Cooling;

3-Bromo-but-1-yne; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere; Cooling;

DOI:10.1039/C7CC00103G

upstream raw materials:

acetoacetic acid methyl ester

propargyl bromide

methanol

4-pentynoic acid

Downstream raw materials:

3,6,8-Trioxo-8-phenyl-octanoic acid methyl ester

7-(4-Acetyl-phenyl)-3-oxo-hept-6-ynoic acid methyl ester