(2S,5R)-5-Isopropenyl-2-methyl-2-((E)-4-oxo-pent-2-enyl)-cyclohexanone

Base Information

• Chemical Name: (2S,5R)-5-Isopropenyl-2-methyl-2-((E)-4-oxo-pent-2-enyl)-cyclohexanone
• CAS No.: 354580-10-2
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.338
• Mol file: 354580-10-2.mol

Synonyms:(2S,5R)-5-Isopropenyl-2-methyl-2-((E)-4-oxo-pent-2-enyl)-cyclohexanone

Chemical Property of (2S,5R)-5-Isopropenyl-2-methyl-2-((E)-4-oxo-pent-2-enyl)-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-5-Isopropenyl-2-methyl-2-((E)-4-oxo-pent-2-enyl)-cyclohexanone

There total 4 articles about (2S,5R)-5-Isopropenyl-2-methyl-2-((E)-4-oxo-pent-2-enyl)-cyclohexanone 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: 91.0%

(E)-5-((6S,9R)-9-Isopropenyl-6-methyl-1,4-dioxa-spiro[4.5]dec-6-yl)-pent-3-en-2-one (354580-09-9) → (2S,5R)-5-Isopropenyl-2-methyl-2-((E)-4-oxo-pent-2-enyl)-cyclohexanone (354580-10-2)

Guidance literature:

With sulfuric acid; silica gel; In dichloromethane;

DOI:10.1016/S0040-4039(01)00638-4

Reference yield:

(R)-2-(2-Benzenesulfonyl-ethyl)-5-isopropenyl-2-methyl-cyclohexanone → (2S,5R)-5-Isopropenyl-2-methyl-2-((E)-4-oxo-pent-2-enyl)-cyclohexanone (354580-10-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: benzene / Heating

2.1: n-BuLi; HMPA / tetrahydrofuran / -78 °C

2.3: aq. H₂SO₄ / 20 °C

3.1: 81 percent / triethylamine / CH₂Cl₂

4.1: 91 percent / aq. H₂SO₄; SiO₂ / CH₂Cl₂

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sulfuric acid; silica gel; triethylamine; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0040-4039(01)00638-4

Reference yield:

(R)-6-(2-Benzenesulfonyl-ethyl)-9-isopropenyl-6-methyl-1,4-dioxa-spiro[4.5]decane → (2S,5R)-5-Isopropenyl-2-methyl-2-((E)-4-oxo-pent-2-enyl)-cyclohexanone (354580-10-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi; HMPA / tetrahydrofuran / -78 °C

1.3: aq. H₂SO₄ / 20 °C

2.1: 81 percent / triethylamine / CH₂Cl₂

3.1: 91 percent / aq. H₂SO₄; SiO₂ / CH₂Cl₂

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sulfuric acid; silica gel; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)00638-4

upstream raw materials:

(E)-5-((6S,9R)-9-Isopropenyl-6-methyl-1,4-dioxa-spiro[4.5]dec-6-yl)-pent-3-en-2-one

4-Benzenesulfonyl-5-((R)-9-isopropenyl-6-methyl-1,4-dioxa-spiro[4.5]dec-6-yl)-pentan-2-one