15764-04-2

Basic information

• Product Name: (4R-cis)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethylidene)naphthalen-2(3H)-one
• Synonyms: alpha-Vetivone; (4R-cis)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethylidene)naphthalen-2(3H)-one; 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethylidene)-, (4R,4aS)-; 4,4a-dimethyl-6-(propan-2-ylidene)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one; (4R,4aS)-4,4a-dimethyl-6-(propan-2-ylidene)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
• CAS NO: 15764-04-2
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.3346
• EINECS: 239-855-1
• Mol File: 15764-04-2.mol

Chemical Properties

• Melting Point: 51.5° (Naves, Perrottet); mp of racemate 30-35° (Marshall, Andersen)
• Boiling Point: 331.6°C at 760 mmHg
• Flash Point: 147.1°C
• Density: 0.98g/cm³
• Vapor Pressure: 0.000154mmHg at 25°C
• Refractive Index: 1.51
• CAS DataBase Reference: (4R-cis)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethylidene)naphthalen-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R-cis)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethylidene)naphthalen-2(3H)-one(15764-04-2)
• EPA Substance Registry System: (4R-cis)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethylidene)naphthalen-2(3H)-one(15764-04-2)

Safety Data

• Hazardous Substances Data: 15764-04-2(Hazardous Substances Data)

Usage

Uses

Used in Perfumery:
(4R-cis)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethylidene)naphthalen-2(3H)-one is used as a fragrance ingredient in the perfumery industry. Its unique scent profile, which can be described as woody and earthy, makes it a valuable addition to modern perfume compositions.
Used in Essential Oils:
(4R-cis)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethylidene)naphthalen-2(3H)-one is also used as a component in essential oils, particularly those derived from Vetiver plants. Its presence in Vetiver essential oil contributes to the oil's highly esteemed status in the perfumery industry, where it serves as a basic ingredient for creating complex and long-lasting fragrances.

Upstream product

• 26431-08-3 (4'S,4'aR)-6'-Isopropylidene-4',4'a-dimethyl-3',4',4'a,5',6',7'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene] 
• 34131-94-7 4-isopropylidene-2-methylcyclohexanone 
• 3102-33-8 trans-3-penten-2-one 
• 20489-50-3 (4R,6R,10S)-4,10-dimethyl-6-(1‘-hydroxyisopropyl)-1-en-3,4,5,6,7,8-hexahydronaphthalen-2-one 
• 72453-44-2 (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone 
• 4674-50-4 (+)-nootkatone 
• 756-79-6 dimethyl methane phosphonate 
• 334775-31-4 (3R,1S)-(-)-3-(5-isopropylidene-1-methyl-2-oxocyclohexyl)butyric acid 
• 38651-65-9 (1R,5S)-(+)-nopinone 
• 72453-41-9 (1R,3S,5R)-3-<(1R)-1-Methyl-3-oxobutyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one 
• 20489-45-6 11-hydroxy-4α,5α,7β-eremophil-1(10)-ene 
• 72453-37-3 (1R,5R)-6,6-Dimethyl-3-(E)-ethylidenebicyclo<3.1.1>heptan-2-one 
• 73068-31-2 (1R,5R)-6,6-Dimethyl-3-(Z)-ethylidenebicyclo<3.1.1>heptan-2-one 
• 72453-43-1 (1R,3S,5R)-3-<1-Methyl-3-methyl-3-butenyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one 

Downstream Products

• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 15719-64-9 methylammonium carbonate 
• 67-64-1 acetone 
• 6211-42-3 (4aS)-6-isopropylidene-4c,4a-dimethyl-(4ar)-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one-(2,4-dinitro-phenylhydrazone) 
• 529-08-8 vetivazulene 

Relevant articles and documents

Enantioselective synthesis of (+)-α-vetivone through the Michael reaction of chiral imines

(+)-α-Vetivone has been synthesised in nine steps. The absolute stereochemistry of the two stereogenic centres is controlled in the same key step involving the stereoselective Michael addition of a chiral imine of 4-isopropylidene-2-methylcyclohexanone to phenyl crotonate.

Synthetic Study of (+)-Nootkatone from (-)-β-Pinene

A facile stereoselective synthesis of (+)-nootkatone (1) has been achieved starting with (+)-nopinone (2b).The key step was the conjugate addition of methallyltrimethylsilane (20b) to trans-3-ethylidenenopinone (16), which was obtainable from 2b on the cross condensation with acetaldehyde followed by acid treatment, giving an adduct with the desired stereochemistry, 24a, as the predominant product.Dione 23, obtained from the adduct on methylation followed by ozonization, afforded nootkatone hydrochloride (26) on treatment with hydrogen chloride.Regioselective dehydrochlorination of the hydrochloride yielded 1.An alternative route in which allyltrimethylsilane was used is also described.