beta-Elemenone

Base Information

• Chemical Name: beta-Elemenone
• CAS No.: 20303-60-0
• Molecular Formula: C15H22O
• Molecular Weight: 218.339
• UNII: 2BH58WTU7X
• DSSTox Substance ID: DTXSID701318217
• Nikkaji Number: J435.957G
• Wikidata: Q67879721
• Metabolomics Workbench ID: 28251
• Mol file: 20303-60-0.mol

Synonyms:beta-Elemenone;20303-60-0;trans-.beta.-Elemenone;(4S)-trans-beta-Elemenone;2BH58WTU7X;beta-Elemenone, (4S)-trans-;ABLPGPHZENVRRH-DZGCQCFKSA-N;CHEBI:169732;DTXSID701318217;LMPR0103080001;Q67879721;(4S,5S)-5-ethenyl-5-methyl-2-propan-2-ylidene-4-prop-1-en-2-ylcyclohexan-1-one;(4S,5S)-5-Ethenyl-5-methyl-4-(1-methylethenyl)-2-(1-methylethylidene)cyclohexanone;Cyclohexanone, 5-ethenyl-5-methyl-4-(1-methylethenyl)-2-(1-methylethylidene)-, (4S,5S)-;Cyclohexanone, 5-ethenyl-5-methyl-4-(1-methylethenyl)-2-(1-methylethylidene)-, (4S-trans)-

Chemical Property of beta-Elemenone

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 369

Purity/Quality:

99% ,98%,Electron Grade , ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C1CC(C(CC1=O)(C)C=C)C(=C)C)C
• Isomeric SMILES: CC(=C1C[C@H]([C@](CC1=O)(C)C=C)C(=C)C)C

Technology Process of beta-Elemenone

There total 18 articles about beta-Elemenone 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: 98.0%

germacrone (6902-91-6) → (4S)-trans-β-elemenone (20303-60-0)

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; In toluene; for 1h; Reflux; Inert atmosphere;

DOI:10.1039/c0ob00467g

Reference yield: 72.0%

(4S,5S)-2-(1-Hydroxy-1-methyl-ethyl)-4-isopropenyl-5-methyl-5-vinyl-cyclohexanone (128261-69-8) → (4S)-trans-β-elemenone (20303-60-0)

Guidance literature:

With pyridine; thionyl chloride; 1. 0 deg C, 2h 2. 5h, RT;

Reference yield:

(1R,5S)-(+)-nopinone (38651-65-9) → (4S)-trans-β-elemenone (20303-60-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 30 min, 0 deg C, 30 min, 2) -78 deg C, 20 min, to r.t., 5 h, r.t., 15 h

2: m-CPBA / CH₂Cl₂ / 1) 0 deg C, 1 h, 2) r.t., 10 h

3: Ac₂O, methanesulfonic acid / CH₂Cl₂ / 1) 0 deg C, 1 h, 2) r.t., 15 h

4: 93 percent / CuBr*Me₂S / tetrahydrofuran / 7 h

5: m-CPBA / CH₂Cl₂ / 1) 0 deg C, 1h, 2) r.t., 10 h

6: Ac₂O, methanesulfonic acid / CH₂Cl₂ / 1) 0 deg C, 1 h, 2) r.t., 15 h

7: 93 percent / m-CPBA / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) r.t., 2 h

8: 1) CuI / 1) THF, -50 deg C, 30 min, 2) -50 deg C, 1.5 h

9: 97 percent / NH₃ (liquid), Li / tetrahydrofuran / 0.5 h

10: 68 percent / BF₃*Et₂O, Zn(OAc)2 / 48 h / Ambient temperature

12: 1) SOCl₂, 2) Al₂O₃ / 1) pyridine, 0 deg C, 2 h, r.t., 2 h, 2) benzene, r.t., 4 h

With aluminum oxide; copper(l) iodide; thionyl chloride; copper(I) bromide dimethylsulfide complex; methanesulfonic acid; boron trifluoride diethyl etherate; zinc diacetate; ammonia; acetic anhydride; lithium; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00025a023

upstream raw materials:

(4S,5S)-2-(1-Hydroxy-1-methyl-ethyl)-4-isopropenyl-5-methyl-5-vinyl-cyclohexanone

(1R,5S)-(+)-nopinone

beta-pinene

(1R,4S,5R)-(+)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one

Downstream raw materials:

(3S,4S)-3-Methyl-4-isopropyl-3-vinyl-1-cyclohexanone

β-elemene

8α-hydroxyelemol

(+)-8α-acetoxyelemol