Bicyclo[2.2.1]heptan-2-one, 5-(acetyloxy)-4,7,7-trimethyl-, (1S,4S,5R)-

Base Information

• Chemical Name: Bicyclo[2.2.1]heptan-2-one, 5-(acetyloxy)-4,7,7-trimethyl-, (1S,4S,5R)-
• CAS No.: 10293-01-3
• Molecular Formula: C12H18O3
• Molecular Weight: 210.273
• Mol file: 10293-01-3.mol

Synonyms:

Chemical Property of Bicyclo[2.2.1]heptan-2-one, 5-(acetyloxy)-4,7,7-trimethyl-, (1S,4S,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[2.2.1]heptan-2-one, 5-(acetyloxy)-4,7,7-trimethyl-, (1S,4S,5R)-

There total 2 articles about Bicyclo[2.2.1]heptan-2-one, 5-(acetyloxy)-4,7,7-trimethyl-, (1S,4S,5R)- 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: 19.0%

bornyl acetate (5655-61-8) → (1S)-camphor (464-48-2,68546-28-1) + (1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-dione (2758-63-6) + 5-oxobornyl acetate (10293-01-3)

Guidance literature:

With ruthenium trichloride; sodium periodate; acetic acid; In water; acetonitrile; at 60 ℃; for 45h;

DOI:10.1016/j.tetlet.2011.06.076

Reference yield:

→ 5-Oxobornylacetat (10293-01-3,28070-36-2,55658-18-9,70630-05-6,71424-72-1,73650-99-4,91839-99-5)

Guidance literature:

(+)-Bornylacetat, CrO3, (CH3CO)2O, Eg., Na-Acetat, 80grad;

Reference yield:

5-oxobornyl acetate (10293-01-3) → (S,S)-2,5-bis(4-fluorophenyl)-1,7,7-trimethylbicyclo[2.2.1]hepta-2,5-diene (1346758-73-3)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium hydroxide / ethanol / 11 h / 20 °C / Inert atmosphere

2: pyridinium chlorochromate / dichloromethane / 13 h / 20 °C / Inert atmosphere

3: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; water; toluene / 1.5 h / Inert atmosphere; Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hexamethylsilazane; sodium carbonate; pyridinium chlorochromate; potassium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; 4: Suzuki coupling;

DOI:10.1002/chem.201102073

upstream raw materials:

bornyl acetate

Downstream raw materials:

2α,5β-dihydroxybornane

(S,S)-2,5-bis(4-fluorophenyl)-1,7,7-trimethylbicyclo[2.2.1]hepta-2,5-diene

(S,S)-2,5-bis(4-chlorophenyl)-1,7,7-trimethylbicyclo[2.2.1]hepta-2,5-diene

(S,S)-1,7,7-trimethyl-2,5-di-p-tolylbicyclo[2.2.1]hepta-2,5-diene