α-Bourbonene

Base Information

• Chemical Name: α-Bourbonene
• CAS No.: 5208-58-2
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• Mol file: 5208-58-2.mol

Synonyms:Cyclobuta[1,2:3,4]dicyclopentene,1,2,3,3a,3b,4,6a,6b-octahydro-3a,6-dimethyl-1-(1-methylethyl)-, (1a,3aa,3bb,6ab,6ba)-; Cyclobuta[1,2:3,4]dicyclopentene, 1,2,3,3a,3bb,4,6ab,6ba-octahydro-1a-isopropyl-3aa,6-dimethyl- (7CI,8CI); (?à)-a-Bourbonene; a-Bourbonene

Chemical Property of α-Bourbonene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of α-Bourbonene

There total 6 articles about α-Bourbonene 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:

(1S,3aS,3bR,6aS,6bR)-1-Isopropyl-3a-methyl-6-methylene-decahydro-cyclobutadicyclopentene (5208-59-3,13828-08-5,68036-15-7,78148-76-2,92998-16-8,119903-95-6,135355-71-4) → α-bourbonene (5208-58-2,13828-07-4,14912-45-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) ozone; 2.) zinc, acetic acid / 1.) ethanol, -78 deg C; 2.) ethanol, water, room temp., 2 h

2: 1.) potassium t-butoxide / tetrahydrofuran / 1 h / -70 °C / 1.) -70 deg C, 1 h

3: palladium acetate / acetonitrile / 1 h / 80 °C

4: tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

With potassium tert-butylate; palladium diacetate; ozone; acetic acid; zinc; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1246/bcsj.61.2672

Reference yield:

(1R)-cis-10-isopropyl-7-methyl-cis-1-transoid-1,2-cis-2-tricyclo<5.3.0.02,6>decane-3-one (13844-03-6) → α-bourbonene (5208-58-2,13828-07-4,14912-45-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) potassium t-butoxide / tetrahydrofuran / 1 h / -70 °C / 1.) -70 deg C, 1 h

2: palladium acetate / acetonitrile / 1 h / 80 °C

3: tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

With potassium tert-butylate; palladium diacetate; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1246/bcsj.61.2672

Reference yield:

Carbonic acid allyl ester (3aR,3bS,6S,6aR,6bS)-6-isopropyl-3b-methyl-3,3a,3b,4,5,6,6a,6b-octahydro-cyclobutadicyclopenten-1-yl ester → α-bourbonene (5208-58-2,13828-07-4,14912-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium acetate / acetonitrile / 1 h / 80 °C

2: tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

With palladium diacetate; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1246/bcsj.61.2672

upstream raw materials:

germacrene D

methyllithium

(1S,3aS,3bR,6aS,6bR)-1-Isopropyl-3a-methyl-6-methylene-decahydro-cyclobutadicyclopentene

(1R)-cis-10-isopropyl-7-methyl-cis-1-transoid-1,2-cis-2-tricyclo<5.3.0.0^2,6>decane-3-one

Refernces