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

Base Information

• Chemical Name: Ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate
• CAS No.: 487-51-4
• Molecular Formula: C10H14 O3
• Molecular Weight: 182.219
• Hs Code.: 2918300090
• European Community (EC) Number: 207-657-4
• NSC Number: 60294
• UNII: 5QME6N6BKP
• DSSTox Substance ID: DTXSID801029631
• Nikkaji Number: J11.631I
• Wikipedia: Hagemann%27s_ester,Hagemann's_ester
• Wikidata: Q5638586
• ChEMBL ID: CHEMBL84047
• Mol file: 487-51-4.mol

Synonyms:487-51-4;Ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate;4-Carbethoxy-3-methyl-2-cyclohexen-1-one;Hagemann's ester;Ethyl 2-methyl-4-oxo-2-cyclohexenecarboxylate;ethyl 2-methyl-4-oxocyclohex-2-ene-1-carboxylate;2-Cyclohexene-1-carboxylic acid, 2-methyl-4-oxo-, ethyl ester;Ethyl 2-methyl-4-oxo-2-cyclohexencarboxylate;5QME6N6BKP;CHEMBL84047;Ethyl 2-methyl-4-oxo-2-cyclohexene-1-carboxylate;EINECS 207-657-4;MFCD00001582;NSC-60294;Hagemann-Ester;NSC60294;4-Carbethoxy-3-methyl-2-cyclohexene-1-one;UNII-5QME6N6BKP;SCHEMBL1141761;DTXSID801029631;BCP09240;BDBM50078829;NSC 60294;AKOS015915880;AS-19704;SY144002;CS-0151639;Ethyl2-methyl-4-oxocyclohex-2-enecarboxylate;FT-0721738;2-Cyclohexene-1-carboxylic acid, ethyl ester;EN300-115192;Q5638586;4-ETHOXYCARBONYL-3-METHYL-2-CYCLOHEXEN-1-ONE;Ethyl 2-methyl-4-oxo-2-cyclohexene-1-carboxylate #;2-Methyl-4-oxo-cyclohex-2-enecarboxylic acid ethyl ester;2-METHYL-4-OXO-2-CYCLOHEXENE-1-CARBOXYLIC ACID ETHYL ESTER;Ethyl 2-methyl-4-oxo-2-cyclohexenecarboxylate, 90%, technical grade

Chemical Property of Ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate

Chemical Property:

• Vapor Pressure: 0.0063mmHg at 25°C
• Refractive Index: n20/D 1.488(lit.)
• Boiling Point: 271.8°Cat760mmHg
• Flash Point: 115.6°C
• Density: 1.082g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 182.094294304
• Heavy Atom Count: 13
• Complexity: 253

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Carbethoxy-3-methyl-2-cyclohexen-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-42/43
• Safety Statements: 23-24/25-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)C1CCC(=O)C=C1C

Technology Process of Ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate

There total 15 articles about Ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate 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%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + ethyl acetoacetate (141-97-9) → 4-carbethoxy-3-methyl-2-cyclohexen-1-one (487-51-4)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; Heating;

DOI:10.1021/jo0623639

Reference yield: 86.0%

4-carbethoxy-3-methyl-2-cyclohexen-1-one oxime → 4-carbethoxy-3-methyl-2-cyclohexen-1-one (487-51-4)

Guidance literature:

With dihydrogen peroxide; tripropylammonium fluorochromate (VI); In acetone; at 0 - 10 ℃; for 8h;

DOI:10.1081/SCC-100104075

Reference yield:

ethyl acetoacetate (141-97-9) → 4-carbethoxy-3-methyl-2-cyclohexen-1-one (487-51-4)

Guidance literature:

With piperidine; formaldehyd; Erwaermen des Reaktionsprodukts mit aethanol. Natriumaethylat und danach mit wss. Essigsaeure behandeln;

DOI:10.1021/jo01215a008 DOI:10.1021/ja01244a040

upstream raw materials:

piperidine

formaldehyd

ethyl acetoacetate

diiodomethane

Downstream raw materials:

2,3-dimethylcyclohex-2-en-1-one

ethyl 2,3-dimethyl-4-oxocyclohex-2-enecarboxylate

ethyl 3-ethyl-2-methyl-4-oxocyclohex-2-enecarboxylate

3-(2-methyl-6-oxo-cyclohex-1-enyl)-propionic acid

Refernces

• 1、 Lv, Shao-Dong,Tian, Tian,Zhang, Liu-Qiang,Xu, Si-Yu,Zhao, Dong-Hai,Wang, Jun-Jie,Fu, Jian-Guo,Li, Yi-Ming,Feng, Chen-Guo. "Total synthesis of (±)-Scrodentoid A". . . Retrieved 2019/11/26.
• 2、 Ramachary, Dhevalapally B.,Ramakumar, Kinthada,Narayana, Vidadala V.. "Organocatalytic cascade reactions based on push-pull dienamine platform: Synthesis of highly substituted anilines". . p. 1458 - 1463. Retrieved 2007/10/03.