3-(2,3-epoxy-1-methyl-4-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

Base Information

• Chemical Name: 3-(2,3-epoxy-1-methyl-4-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene
• CAS No.: 114790-57-7
• Molecular Formula: C₁₈H₂₀O₃S
• Molecular Weight: 316.421
• Mol file: 114790-57-7.mol

Synonyms:3-(2,3-epoxy-1-methyl-4-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

Chemical Property of 3-(2,3-epoxy-1-methyl-4-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2,3-epoxy-1-methyl-4-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

There total 5 articles about 3-(2,3-epoxy-1-methyl-4-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene 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:

4-hydroxy-4-methyl-2-cyclopenten-1-one (61882-64-2,95886-59-2,159448-23-4) → 3-(2,3-epoxy-1-methyl-4-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene (114790-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / H₂O₂, 6N NaOH / methanol / 1.) 15-20 deg C, 40 min; 2.) 20-25 deg C, 2.5 h

2: 55 percent / methanesulfonyl chloride, triethylamine / diethyl ether / 1.) 0 deg C, 2.) 25 deg C, 30 min

3: 1.) LDA / 1.) THF, -78, 30 min; 2.) THF, HMPA, -78, 15 min

With sodium hydroxide; dihydrogen peroxide; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; In methanol; diethyl ether;

DOI:10.1021/ja00222a036

Reference yield:

1-methyl-2-cyclopenten-1,4-diol (114790-77-1) → 3-(2,3-epoxy-1-methyl-4-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene (114790-57-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / 3A molecular sieves, pyridinium chlorochromate / CH₂Cl₂ / 3 h / 25 °C

2: 65 percent / H₂O₂, 6N NaOH / methanol / 1.) 15-20 deg C, 40 min; 2.) 20-25 deg C, 2.5 h

3: 55 percent / methanesulfonyl chloride, triethylamine / diethyl ether / 1.) 0 deg C, 2.) 25 deg C, 30 min

4: 1.) LDA / 1.) THF, -78, 30 min; 2.) THF, HMPA, -78, 15 min

With sodium hydroxide; 3 A molecular sieve; dihydrogen peroxide; methanesulfonyl chloride; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/ja00222a036

Reference yield:

2,3-epoxy-4-hydroxy-4-methylcyclopentan-1-one (114790-79-3) → 3-(2,3-epoxy-1-methyl-4-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene (114790-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / methanesulfonyl chloride, triethylamine / diethyl ether / 1.) 0 deg C, 2.) 25 deg C, 30 min

2: 1.) LDA / 1.) THF, -78, 30 min; 2.) THF, HMPA, -78, 15 min

With methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; In diethyl ether;

DOI:10.1021/ja00222a036

upstream raw materials:

(2-Cyclohexenyl)(phenyl)sulfoxid

2,3-epoxy-4-methyl-4-cyclopentenone

4-hydroxy-4-methyl-2-cyclopenten-1-one

1-methyl-2-cyclopenten-1,4-diol