beta-Bergamotene

Base Information

• Chemical Name: beta-Bergamotene
• CAS No.: 6895-56-3
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.3511
• European Community (EC) Number: 881-679-8
• UNII: 2H330CKD1Z
• Mol file: 6895-56-3.mol

Synonyms:.beta.-Bergamotene;(E)-.beta.-Bergamotene;DGZBGCMPRYFWFF-ZYOSVBKOSA-N;6895-56-3;NORPINANE, 6-METHYL-2-METHYLENE-6-(4-METHYL-3-PENTENYL)-;BICYCLO(3.1.1)HEPTANE, 6-METHYL-2-METHYLENE-6-(4-METHYL-3-PENTEN-1-YL)-

Chemical Property of beta-Bergamotene

Chemical Property:

• Vapor Pressure: 0.0202mmHg at 25°C
• Boiling Point: 260.1°C at 760 mmHg
• Flash Point: 100.8°C
• Density: 0.89g/cm³
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 293

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC1(C2CCC(=C)C1C2)C)C
• Isomeric SMILES: CC(=CCCC1([C@H]2CCC(=C)[C@@H]1C2)C)C

Technology Process of beta-Bergamotene

There total 33 articles about beta-Bergamotene 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: 52.0%

[(1S,5R,7R)-7-Methyl-2-methylene-7-(4-methyl-pent-3-enyl)-bicyclo[3.1.1]hept-(6E)-ylidene]-hydrazine → β-trans-bergamotene (6895-56-3,15438-93-4,15438-94-5,35334-59-9,55123-21-2,97232-39-8) + (1R*,5R*,6S*)-2,6-dimethyl-6-(4-methyl-3-pentenyl)bicyclo[3.1.1]hept-2-ene

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; at 85 ℃; for 15h;

DOI:10.1271/bbb.66.1415

Reference yield:

C22H32N2O2S → β-trans-bergamotene (6895-56-3,15438-93-4,15438-94-5,35334-59-9,55123-21-2,97232-39-8)

Guidance literature:

With sodium acetate; In acetic acid;

DOI:10.1021/ja00754a055

Reference yield:

trans-6-Methyl-6-(3-oxopropyl)-bicyclo<3.1.1>heptan-3-on (35315-92-5) → β-trans-bergamotene (6895-56-3,15438-93-4,15438-94-5,35334-59-9,55123-21-2,97232-39-8)

Guidance literature:

Multi-step reaction with 8 steps

1: (i) nBuLi, (ii) /BRN= 6775450/

2: NaH / 1,2-dimethoxy-ethane

3: NaH / tetrahydrofuran; hexamethylphosphoric acid triamide

4: (i) NaBH₄, (ii) aq. HCl

5: NaBH₄

6: PBr₃ / diethyl ether

7: NaH / dimethylsulfoxide

8: NaOAc*3H₂O / acetic acid

With sodium tetrahydroborate; sodium acetate; phosphorus tribromide; sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; acetic acid; dimethyl sulfoxide;

DOI:10.1021/ja00754a055

upstream raw materials:

(+/-)-1-oxo-β-trans-bergamotene

E,E and Z,E-farnesic acid

(2E,6E)-3,7,11-Trimethyl-dodeca-2,6,10-trienoyl chloride

trans geranyl acetone