(1R)-5-[(1S)-3-Hydroxy-1,5-dimethylhexyl]-2-methylenecyclohexanol

Base Information

• Chemical Name: (1R)-5-[(1S)-3-Hydroxy-1,5-dimethylhexyl]-2-methylenecyclohexanol
• CAS No.: 262290-97-1
• Molecular Formula: C₁₅H₂₈O₂
• Molecular Weight: 240.386
• Mol file: 262290-97-1.mol

Synonyms:

Chemical Property of (1R)-5-[(1S)-3-Hydroxy-1,5-dimethylhexyl]-2-methylenecyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-5-[(1S)-3-Hydroxy-1,5-dimethylhexyl]-2-methylenecyclohexanol

There total 8 articles about (1R)-5-[(1S)-3-Hydroxy-1,5-dimethylhexyl]-2-methylenecyclohexanol 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:

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → (1R)-5-[(1S)-3-Hydroxy-1,5-dimethylhexyl]-2-methylenecyclohexanol (262290-97-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-BuLi; TMEDA / hexane / 20 °C

1.2: hexane / -78 - 0 °C

2.1: activity grade I alumina / diethyl ether / 2 h

3.1: baker's yeast; resin XAD; glucose / H₂O / 96 h / 20 °C / Microbiological reaction

4.1: 93 percent / PCC / CH₂Cl₂ / 1 h / 20 °C

5.1: 80 percent / tetrahydrofuran / 1 h / 0 °C

6.1: MCPBA / CH₂Cl₂ / 1 h / 0 °C

7.1: LDA / tetrahydrofuran / 2 h / Heating

With aluminum oxide; n-butyllithium; baker's yeast; D-glucose; N,N,N,N,-tetramethylethylenediamine; resin XAD; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 1.1: Metallation / 1.2: Formylation / 2.1: Isomerization / 3.1: Reduction / 4.1: Oxidation / 5.1: Grignard reaction / 6.1: Epoxidation / 7.1: Isomerization;

Reference yield:

(R)-3-(4-methyl-cyclohex-3-enyl)-but-3-enal (77614-31-4) → (1R)-5-[(1S)-3-Hydroxy-1,5-dimethylhexyl]-2-methylenecyclohexanol (262290-97-1)

Guidance literature:

Multi-step reaction with 6 steps

1: activity grade I alumina / diethyl ether / 2 h

2: baker's yeast; resin XAD; glucose / H₂O / 96 h / 20 °C / Microbiological reaction

3: 93 percent / PCC / CH₂Cl₂ / 1 h / 20 °C

4: 80 percent / tetrahydrofuran / 1 h / 0 °C

5: MCPBA / CH₂Cl₂ / 1 h / 0 °C

6: LDA / tetrahydrofuran / 2 h / Heating

With aluminum oxide; baker's yeast; D-glucose; resin XAD; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; water; 1: Isomerization / 2: Reduction / 3: Oxidation / 4: Grignard reaction / 5: Epoxidation / 6: Isomerization;

Reference yield:

(S)-3-((R)-4-methylcyclohex-3-en-1-yl)butanal (128300-30-1) → (1R)-5-[(1S)-3-Hydroxy-1,5-dimethylhexyl]-2-methylenecyclohexanol (262290-97-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / tetrahydrofuran / 1 h / 0 °C

2: MCPBA / CH₂Cl₂ / 1 h / 0 °C

3: LDA / tetrahydrofuran / 2 h / Heating

With 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1: Grignard reaction / 2: Epoxidation / 3: Isomerization;

upstream raw materials:

D-limonene

(R)-3-(4-methyl-cyclohex-3-enyl)-but-3-enal

(S)-3-((R)-4-methylcyclohex-3-en-1-yl)butanal

9-Hydroxy-methyl-Δ¹-p-menthen

Downstream raw materials:

(R)-4-((S)-1,5-Dimethyl-3-oxo-hexyl)-cyclohex-1-enecarbaldehyde

(+)-epijuvabione

(+)-Epitodomatuic acid