2-Cyclohexen-1-ol, 4-[(1E,3R)-3-hydroxy-1-butenyl]-3,5,5-trimethyl-, (1R,4R)-

Base Information

• Chemical Name: 2-Cyclohexen-1-ol, 4-[(1E,3R)-3-hydroxy-1-butenyl]-3,5,5-trimethyl-, (1R,4R)-
• CAS No.: 68831-82-3
• Molecular Formula: C13H22O2
• Molecular Weight: 210.316
• Mol file: 68831-82-3.mol

Synonyms:

Chemical Property of 2-Cyclohexen-1-ol, 4-[(1E,3R)-3-hydroxy-1-butenyl]-3,5,5-trimethyl-, (1R,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Cyclohexen-1-ol, 4-[(1E,3R)-3-hydroxy-1-butenyl]-3,5,5-trimethyl-, (1R,4R)-

There total 12 articles about 2-Cyclohexen-1-ol, 4-[(1E,3R)-3-hydroxy-1-butenyl]-3,5,5-trimethyl-, (1R,4R)- 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: 77.0%

C19H36O2Si (1354005-97-2) → (3R,6R,7E,9R)-3,9-dihydroxy-4,7-megastigmadiene (68831-82-3)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 40 ℃; for 4h;

DOI:10.1016/j.tetlet.2011.10.151

Reference yield:

C21H30O3 → (3R,6R,7E,9R)-3,9-dihydroxy-4,7-megastigmadiene (68831-82-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C

2.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 6 h / -40 °C

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / 4 h / 40 °C

3.2: 12 h / -78 - 0 °C

4.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 20 °C

5.1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine / water; acetonitrile / 1.5 h / 80 °C

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / pH 7 / aq. phosphate buffer

7.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 4 h / 40 °C

With pyridine; 2,6-dimethylpyridine; borane-THF; palladium diacetate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; water; acetonitrile; 5.1: Heck reaction;

DOI:10.1016/j.tetlet.2011.10.151

Reference yield:

C16H24O3 (1354005-88-1) → (3R,6R,7E,9R)-3,9-dihydroxy-4,7-megastigmadiene (68831-82-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: mercury(II) diacetate / 36 h / Reflux

2.1: methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide) / dichloromethane / 0.25 h / -78 °C

3.1: n-butyllithium / tetrahydrofuran

3.2: 2 h / -78 °C

4.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C

5.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 6 h / -40 °C

6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / 4 h / 40 °C

6.2: 12 h / -78 - 0 °C

7.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 20 °C

8.1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine / water; acetonitrile / 1.5 h / 80 °C

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / pH 7 / aq. phosphate buffer

10.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 4 h / 40 °C

With pyridine; 2,6-dimethylpyridine; n-butyllithium; borane-THF; mercury(II) diacetate; palladium diacetate; Dess-Martin periodane; pyridine hydrogenfluoride; methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide); triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; water; acetonitrile; 2.1: Claisen rearrangement / 8.1: Heck reaction;

DOI:10.1016/j.tetlet.2011.10.151

upstream raw materials:

(6R,7E,9R)-9-Hydroxy-megastigma-4,7-dien-3-ons

C₂₇H₄₄O₃Si

C₁₆H₂₄O₃

C₁₉H₃₆O₂Si