Methyl 1-methyl-4-oxocyclohex-2-ene-1-carboxylate

Base Information

• Chemical Name: Methyl 1-methyl-4-oxocyclohex-2-ene-1-carboxylate
• CAS No.: 1523-89-3
• Molecular Formula: C9H12O3
• Molecular Weight: 168.192
• DSSTox Substance ID: DTXSID40502659
• Nikkaji Number: J1.455.137I
• Mol file: 1523-89-3.mol

Synonyms:methyl 1-methyl-4-oxocyclohex-2-ene-1-carboxylate;1523-89-3;Methyl 1-methyl-4-oxo-2-cyclohexenecarboxylate;SCHEMBL11083110;DTXSID40502659;SVRHDMOUJKJELT-UHFFFAOYSA-N;methyl 1-methyl-4-oxo-2-cyclohexene-1-carboxylate

Chemical Property of Methyl 1-methyl-4-oxocyclohex-2-ene-1-carboxylate

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 168.078644241
• Heavy Atom Count: 12
• Complexity: 242

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC(=O)C=C1)C(=O)OC

Technology Process of Methyl 1-methyl-4-oxocyclohex-2-ene-1-carboxylate

There total 9 articles about Methyl 1-methyl-4-oxocyclohex-2-ene-1-carboxylate 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: 95.1%

4-carbomethoxy-3-methoxy-4-methyl-1-<(trimethylsilyl)oxy>cyclohex-1-ene (127131-75-3,127131-76-4) → methyl 1-methyl-4-oxo-2-cyclohexene-1-carboxylate (1523-89-3)

Guidance literature:

With 2,3,5-trimethyl-pyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetone; at -78 ℃; for 0.0833333h;

DOI:10.1021/jo00298a066

Reference yield: 68.0%

1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene (59414-23-2) + methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7) → methyl 1-methyl-4-oxo-2-cyclohexene-1-carboxylate (1523-89-3)

Guidance literature:

In toluene; at 130 ℃; for 16h;

Reference yield:

methyl 2-methyl-3-oxopropanoate (51673-64-4) + methyl vinyl ketone (78-94-4,25038-87-3) → methyl 1-methyl-4-oxo-2-cyclohexene-1-carboxylate (1523-89-3)

Guidance literature:

Multistep reaction; (i) KOtBu, (ii) piperidine acetate, AcOH;

upstream raw materials:

methyl 2-methyl-3-oxopropanoate

methyl vinyl ketone

danishefsky's diene

methacrylic acid methyl ester

Downstream raw materials:

methyl 1-methyl-4-oxo-1-cyclohexanecarboxylate

C₁₁H₁₆O₃

C₉H₁₁IO₃