Wine lactone

Base Information

• Chemical Name: Wine lactone
• CAS No.: 57743-63-2
• Molecular Formula: C10H14O2
• Molecular Weight: 166.22
• European Community (EC) Number: 611-573-7
• DSSTox Substance ID: DTXSID90886239
• Nikkaji Number: J892.295K
• Wikipedia: Wine_lactone
• Wikidata: Q106654061
• Metabolomics Workbench ID: 43987
• Mol file: 57743-63-2.mol

Synonyms:Wine lactone;57743-63-2;3,6-Dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one;2(3H)-Benzofuranone, 3a,4,5,7a-tetrahydro-3,6-dimethyl-;3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-1-benzofuran-2-one;MFCD08437481;3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-one;p-Menth-1-en-9,3-olide;SCHEMBL2004584;3a,4,5,7a-tetrahydro-3,6-dimethyl- 2(3H)-benzofuranone;DTXSID90886239;NQWBFQXRASPNLB-UHFFFAOYSA-N;AKOS006290101;BS-50262;SY281098;CS-0152878;F10704;Q424963;3a,4,5,7a-tetrahydro-3,6-dimethyl-2(3H)-benzofuranone;tetrahydro-3,6-dimethyl-2(3H)-benzofuranone, 3a,4,5,7a;3a,4,5,7a-tetrahydro-3,6-dimethyl-2(3H)-benzo[b]furanone;3,6-Dimethyl-3alpha,4,5,7alpha-tetrahydro-1-benzofuran-2(3H)-one;2-(2-HYDROXY-4-METHYL-3-CYCLOHEXENYL)PROPIONIC ACID GAMMA-LACTONE;2-(2-HYDROXY-4-METHYL-3-CYCLOHEXENYL)PROPIONICACIDGAMMA-LACTONE;wine lactone (3a,4,5,7a-Tetrahydro-3,6-dimethyl-2(3H)-benzofuranone)

Chemical Property of Wine lactone

Chemical Property:

• PSA: 26.30000
• LogP: 1.90420
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 166.099379685
• Heavy Atom Count: 12
• Complexity: 242

Purity/Quality:

98.5% ^*data from raw suppliers

3,6-Dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CCC(=CC2OC1=O)C

Technology Process of Wine lactone

There total 3 articles about Wine lactone 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:

C10H14O3 (1415228-03-3) → epi-wine lactone (57743-63-2) + (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (3R,3aR,7aS)-3,6-dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one (182699-78-1)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; formic acid; ((R,R)-Ts-DENEB)RuCl; In methanol; at 60 ℃; for 20h; Reagent/catalyst;

Reference yield:

6-(1'-methylcarbonyl-ethyl)-3-methyl-2-cyclohexenone (83037-73-4) → epi-wine lactone (57743-63-2) + (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (3R,3aR,7aS)-3,6-dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one (182699-78-1)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; formic acid; ((R,R)-Ts-DENEB)RuCl; In methanol; at 60 ℃; for 70h; Reagent/catalyst;

Reference yield:

methyl 3-(methoxycarbonyl)-2-methyl-4-oxopentanoate (35493-66-4) → epi-wine lactone (57743-63-2) + (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (3R,3aR,7aS)-3,6-dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one (182699-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hydroxide / dimethyl sulfoxide / 0.5 h / 40 °C

1.2: 3 h / 40 °C

2.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; ((R,R)-Ts-DENEB)RuCl / methanol / 70 h / 60 °C

With 1,4-diaza-bicyclo[2.2.2]octane; formic acid; ((R,R)-Ts-DENEB)RuCl; potassium hydroxide; In methanol; dimethyl sulfoxide;

upstream raw materials:

methyl 3-(methoxycarbonyl)-2-methyl-4-oxopentanoate

C₁₀H₁₄O₃

6-(1'-methylcarbonyl-ethyl)-3-methyl-2-cyclohexenone

Refernces