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
• Article Data: 3

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

α-Vetivone, is a component of Vetiver essential oil which is a highly esteemed basic ingredient of modern perfumery, hvaing a woody, earthy scent.

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 
• 756-79-6 dimethyl methane phosphonate 
• 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 
• 72453-40-8 (1R,3S,5R)-3-<1-Methyl-3-butenyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one 
• 72453-42-0 (1R,3S,5S)-6,6-Dimethyl-3-<1-methyl-3-methyl-3-butenyl>bicyclo<3.1.1.>heptan-2-one 
• 72453-39-5 (1R,3S,5S)-6,6-Dimethyl-3-<1-methyl-3-butenyl>bicyclo<3.1.1>heptan-2-one 
• 72453-33-9 (1R,5R)-6,6-Dimethyl-2-<(trimethylsilyl)oxy>bicyclo<3.1.1>hept-2-ene 
• 72453-38-4 (1R,3R,5R)-6,6-Dimethyl-3-(1-hydroxyethyl)bicyclo<3.1.1>heptan-2-one 
• 72453-41-9 (1R,3S,5R)-3-<(1R)-1-Methyl-3-oxobutyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one 

Downstream Products

• 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) 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 15719-64-9 methylammonium carbonate 
• 67-64-1 acetone 
• 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.

Structure and absolute configuration of kusunol.

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