Methyl 5-diazo-4-oxopentanoate

Base Information

• Chemical Name: Methyl 5-diazo-4-oxopentanoate
• CAS No.: 7770-06-1
• Molecular Formula: C6H9N2O3+
• Molecular Weight: 157.1467
• NSC Number: 39481
• DSSTox Substance ID: DTXSID80998916
• Nikkaji Number: J1.867.091G
• Wikidata: Q82991721
• Mol file: 7770-06-1.mol

Synonyms:7770-06-1;methyl 5-diazo-4-oxopentanoate;DTXSID80998916;NSC39481;NSC-39481;4-Oxo-5-diazovaleric acid methyl ester

Chemical Property of Methyl 5-diazo-4-oxopentanoate

Chemical Property:

• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 156.05349212
• Heavy Atom Count: 11
• Complexity: 206

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC(=O)C=[N+]=[N-]

Technology Process of Methyl 5-diazo-4-oxopentanoate

There total 5 articles about Methyl 5-diazo-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: 90.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + succinic acid monomethylester chloride (1490-25-1) → methyl 5-diazo-4-oxopentanoate (7770-06-1)

Guidance literature:

at 0 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(02)02810-1

Reference yield: 80.0%

diazomethyl-trimethyl-silane (18107-18-1) + succinic acid monomethylester chloride (1490-25-1) → methyl 5-diazo-4-oxopentanoate (7770-06-1)

Guidance literature:

In diethyl ether; acetonitrile; at 25 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jacs.6b01428

Reference yield: 30.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + succinic acid anhydride (108-30-5) → methyl 5-diazo-4-oxopentanoate (7770-06-1)

Guidance literature:

In diethyl ether; at 0 - 5 ℃; for 480h;

upstream raw materials:

diazomethane

succinic acid monomethylester chloride

succinic acid anhydride

methyl hydrogen succinate

Downstream raw materials:

methyl 5-bromo-4-oxopentanoate

5-{(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-3,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrol-2-ylsulfanyl}-4-oxo-pentanoic acid methyl ester

5-{(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-3,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrol-2-ylsulfanyl}-4-oxo-pentanoic acid methyl ester

(S)-1-cyclohexylallyl acetate