Methyl 4-oxocycloheptanecarboxylate

Base Information

• Chemical Name: Methyl 4-oxocycloheptanecarboxylate
• CAS No.: 17607-00-0
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.208
• Hs Code.: 2918300090
• European Community (EC) Number: 802-245-6
• DSSTox Substance ID: DTXSID10455729
• Mol file: 17607-00-0.mol

Synonyms:METHYL 4-OXOCYCLOHEPTANECARBOXYLATE;17607-00-0;Methyl 4-oxocycloheptane-1-carboxylate;4-Oxo-cycloheptanecarboxylic acid methyl ester;Cycloheptanecarboxylic acid, 4-oxo-, methyl ester;SCHEMBL9633492;DTXSID10455729;MFCD11053676;AKOS006306087;SB34298;METHYL4-OXOCYCLOHEPTANECARBOXYLATE;AS-37974;CS-0340929;EN300-6486626

Chemical Property of Methyl 4-oxocycloheptanecarboxylate

Chemical Property:

• PSA: 43.37000
• LogP: 1.30880
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 170.094294304
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl4-oxocycloheptanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCCC(=O)CC1

Technology Process of Methyl 4-oxocycloheptanecarboxylate

There total 8 articles about Methyl 4-oxocycloheptanecarboxylate 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: 94.0%

methyl 5-oxobicyclo<4.1.0>heptane-1-carboxylate (154184-57-3) → methyl 4-oxocycloheptane-1-carboxylate (17607-00-0)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; methanol; for 0.0333333h; Ambient temperature;

DOI:10.1016/S0040-4039(98)01749-3

Reference yield: 82.0%

ethene (74-85-1) + methyl 2-oxocyclopentane-1-carboxylate (10472-24-9,265317-94-0) → methyl 4-oxocycloheptane-1-carboxylate (17607-00-0)

Guidance literature:

With fac-iridium(III) tris(1-(4-trifluoromethylphenyl)-3-methylbenzimidazolin-2-ylidene); triethylamine; In toluene; at 20 ℃; for 48h; under 1500.15 Torr; Reagent/catalyst; Pressure; Solvent; Catalytic behavior; Schlenk technique; Irradiation;

DOI:10.1002/anie.202112695

Reference yield: 45.0%

methyl cycloheptanecarboxylate (60433-00-3) → methyl 4-oxocycloheptane-1-carboxylate (17607-00-0) + methyl 3-oxocycloheptane-1-carboxylate (37746-13-7)

Guidance literature:

With [Fe^II(N,N'-(bis(2-pyridylmethyl)-(S,S)-2,2'-bipyrrolidine))(CH₃CN)₂](SbF₆)₂; dihydrogen peroxide; acetic acid; In acetonitrile; at 25 ℃; for 0.5h; regioselective reaction;

DOI:10.1126/science.1183602

upstream raw materials:

methyl 5-oxobicyclo<4.1.0>heptane-1-carboxylate

3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

methyl cyclohex-1-ene-1-carboxylate

3-hydroxy-1-cyclohexenecarboxylic acid methyl ester

Refernces

• 1、 Lee, Phil Ho,Lee, Jukyoung. "SmI2-induced ring expansion reactions of alkyl (n+1)- oxobicyclo[n.1.0]alkane-1-carboxylates". . p. 7889 - 7892. Retrieved 1998.
• 2、 Chen, Mark S.,White, M. Christina. "Combined effects on selectivity in Fe-catalyzed methylene oxidation". scheme or table. p. 533 - 571. Retrieved 2010/10/05.