Norbourbonone

Base Information

• Chemical Name: Norbourbonone
• CAS No.: 13844-03-6
• Molecular Formula: C14H22O
• Molecular Weight: 206.328
• Mol file: 13844-03-6.mol

Synonyms:11-Nor-bourbonanon-(1);11-norbourbonan-1-one;(-)-norbourbonene;(3aR,3bS,6S,6aR,6bS)-6-Isopropyl-3b-methyl-octahydro-cyclobutadicyclopenten-1-one;(Nor-bourbonon);(-)-norbourbonone;1-norbourbonanone;2-Methyl-5-isopropyl-tricyclo<5.3.0.0.2,6>decan-8-on;

Chemical Property of Norbourbonone

Chemical Property:

• Melting Point: 24.5-25.5 °C
• Boiling Point: 283.6±8.0 °C(Predicted)
• PSA: 17.07000
• Density: 1.017±0.06 g/cm3(Predicted)
• LogP: 3.28380

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Norbourbonone

There total 1 articles about Norbourbonone 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (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)

Guidance literature:

Multi-step reaction with 10 steps

2: cc HCl / methanol

3: pyridine / methanol

4: 25 percent / Irradiation

5: 95 percent

7: 2.) NaBH₄ / 1.)Pd/C in AcOEt; 2.) MeOH

8: 1.)tosylation 2.) refluxing DME

9: 85 percent / LiAlH₄

10: 1.) LiAlH₄ 2.) p-TsOH / 2.) acetone

With pyridine; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; toluene-4-sulfonic acid; In methanol;

DOI:10.1016/S0040-4039(00)87626-1

Reference yield: 98.0%

(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) + Methyltriphenylphosphonium bromide (1779-49-3) → (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)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; for 20h; Ambient temperature;

Reference yield: 98.0%

(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) → (-)-β-bourbonene (5208-59-3,13828-08-5,68036-15-7,78148-76-2,92998-16-8,119903-95-6,135355-71-4)

Guidance literature:

DOI:10.1016/S0040-4039(00)87626-1

upstream raw materials:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

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

(-)-β-bourbonene

α-bourbonene