Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethylidene)-, (4aR-trans)-

Base Information

• Chemical Name: Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethylidene)-, (4aR-trans)-
• CAS No.: 6813-21-4
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• Nikkaji Number: J109.968J
• Wikidata: Q105309251
• Metabolomics Workbench ID: 163675
• Mol file: 6813-21-4.mol

Synonyms:Eudesma-3,7(11)-diene;Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethylidene)-, (4aR-trans)-;3,7(11)-Selinadiene;Selina-3,7(11)-diene;WNRBYZQFEBIUGD-LSDHHAIUSA-N;4a,8-Dimethyl-2-(1-methylethylidene)-1,2,3,4,4a,5,6,8a-octahydronaphthalene-, (4aR-trans)-;(4aR,8aR)-5,8a-dimethyl-3-propan-2-ylidene-1,2,4,4a,7,8-hexahydronaphthalene

Chemical Property of Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethylidene)-, (4aR-trans)-

Chemical Property:

• Vapor Pressure: 0.0119mmHg at 25°C
• Boiling Point: 269.6±10.0 °C(Predicted)
• Density: 0.902±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C, Light sensitive
• Solubility.: Chloroform (Slightly), Hexane (Slightly)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 315

Purity/Quality:

Selina-3,7(11)-diene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CCCC2(C1CC(=C(C)C)CC2)C
• Isomeric SMILES: CC1=CCC[C@]2([C@H]1CC(=C(C)C)CC2)C
• Uses: Selina-3,7(11)-diene is an essential oil component, shown to have antioxidant and antimicrobial properties.

Technology Process of Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethylidene)-, (4aR-trans)-

There total 11 articles about Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethylidene)-, (4aR-trans)- 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: 75.0%

3,9-dimethyl-6-isopropylidene-1,3,9-decatriene (122040-87-3) → selina-3,7(11)-diene (6813-21-4,58893-87-1,68926-80-7)

Guidance literature:

In toluene; at 190 ℃; for 110h;

DOI:10.1016/S0040-4020(01)81307-7

Reference yield:

germacrene B (15423-57-1,17091-09-7,32663-54-0,69460-23-7,69609-32-1) → (4aR,8aS)-4a-methyl-1-methylene-7-(propan-2-ylidene)decahydronaphthalene (515-17-3) + (4aR,8aR)-5,8a-dimethyl-3-propan-2-ylidene-1,2,4,4a,7,8-hexahydronaphthalene (58893-87-1,68926-80-7,6813-21-4)

Guidance literature:

With hydrogenchloride; In solid; at 185 ℃; for 5h; Product distribution;

DOI:10.1016/0031-9422(80)83195-5

Reference yield:

1-bromo-2-bromomethyl-3-methyl-but-2-ene (26430-96-6) → selina-3,7(11)-diene (6813-21-4,58893-87-1,68926-80-7)

Guidance literature:

Multi-step reaction with 3 steps

2: 97 percent / hexane / Heating

3: toluene / 110 h / 190 °C

In hexane; toluene;

DOI:10.1039/c39880001188

upstream raw materials:

2-(4-nitro-benzoyloxy)-2-((1R)-4c-methyl-4t-vinyl-3c-isopropenyl-cyclohexyl-(r))-propane

germacrene B

carbon tetrabromide

lithium dimethylcuprate