(S)-6-((R)-3-hydroxy-4-methylpent-4-enyl)-3-methoxy-6-methylcyclohex-2-enone

Base Information

• Chemical Name: (S)-6-((R)-3-hydroxy-4-methylpent-4-enyl)-3-methoxy-6-methylcyclohex-2-enone
• CAS No.: 1412281-19-6
• Molecular Formula: C₁₄H₂₂O₃
• Molecular Weight: 238.327
• Mol file: 1412281-19-6.mol

Synonyms:(S)-6-((R)-3-hydroxy-4-methylpent-4-enyl)-3-methoxy-6-methylcyclohex-2-enone

Chemical Property of (S)-6-((R)-3-hydroxy-4-methylpent-4-enyl)-3-methoxy-6-methylcyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6-((R)-3-hydroxy-4-methylpent-4-enyl)-3-methoxy-6-methylcyclohex-2-enone

There total 3 articles about (S)-6-((R)-3-hydroxy-4-methylpent-4-enyl)-3-methoxy-6-methylcyclohex-2-enone 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:

C13H20O3 (1412280-81-9) + methyl iodide (74-88-4) → (S)-6-((R)-3-hydroxy-4-methylpent-4-enyl)-3-methoxy-6-methylcyclohex-2-enone (1412281-19-6) + (R)-6-((R)-3-hydroxy-4-methylpent-4-enyl)-3-methoxy-6-methylcyclohex-2-enone (1412280-84-2)

Guidance literature:

C₁₃H₂₀O₃; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 ℃; for 0.583333h;

methyl iodide; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 - 0 ℃; for 2h;

DOI:10.1039/c2ob26532j

Reference yield:

6-[3'-hydroxy-4'-methylpent-4'-en-1'-yl]-3-methoxycyclohex-2-en-1-one (1312767-99-9) → (S)-6-((R)-3-hydroxy-4-methylpent-4-enyl)-3-methoxy-6-methylcyclohex-2-enone (1412281-19-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

2.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / dichloromethane; toluene / 10.75 h / -78 - -70 °C

3.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.58 h / -78 °C

3.2: 2 h / -78 - 0 °C

With dimethylsulfide borane complex; Dess-Martin periodane; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane; ethylbenzene; toluene;

DOI:10.1039/c2ob26532j

Reference yield:

3-methoxy-6-(4-methyl-3-oxopent-4-enyl)cyclohex-2-enone (1412280-60-4) → (S)-6-((R)-3-hydroxy-4-methylpent-4-enyl)-3-methoxy-6-methylcyclohex-2-enone (1412281-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / dichloromethane; toluene / 10.75 h / -78 - -70 °C

2.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.58 h / -78 °C

2.2: 2 h / -78 - 0 °C

With dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane; ethylbenzene; toluene;

DOI:10.1039/c2ob26532j

upstream raw materials:

6-[3'-hydroxy-4'-methylpent-4'-en-1'-yl]-3-methoxycyclohex-2-en-1-one

3-methoxy-6-(4-methyl-3-oxopent-4-enyl)cyclohex-2-enone

C₁₃H₂₀O₃

methyl iodide

Downstream raw materials:

3-(4-methoxy-1-methyl-2-oxocyclohex-3-enyl)-propionaldehyde

(S)-6-(3-hydroxypropyl)-3-methoxy-6-methylcyclohex-2-enone