alpha-Vetivone

Base Information

• Chemical Name: alpha-Vetivone
• CAS No.: 15764-04-2
• Deprecated CAS: 6152-50-7,89-89-4
• Molecular Formula: C15H22 O
• Molecular Weight: 218.339
• European Community (EC) Number: 239-855-1
• UNII: WA62V77MMV
• DSSTox Substance ID: DTXSID60884848
• Nikkaji Number: J9.661J
• Wikipedia: %CE%91-Vetivone
• Wikidata: Q8083965
• Metabolomics Workbench ID: 69298
• Mol file: 15764-04-2.mol

Synonyms:alpha-Vetivone;Isonootkaton;Isonootkatone;15764-04-2;UNII-WA62V77MMV;WA62V77MMV;C09744;(+)-Isonootkatone;EINECS 239-855-1;2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethylidene)-, (4R,4aS)-;(+)-.alpha.-Vetivon;(+)-.alpha.-Vetivone;(4R-cis)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethylidene)naphthalen-2(3H)-one;4.beta.H,5.alpha.-Eremophila-1(10),7(11)-dien-2-one;.alpha.-Vetivone;2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethylidene)-, (4R-cis)-;(4R,4aS)-4,4a-dimethyl-6-propan-2-ylidene-4,5,7,8-tetrahydro-3H-naphthalen-2-one;SCHEMBL1545445;.ALPHA.-VETIVONE [MI];CHEBI:10339;DTXSID60884848;Q8083965;(4R,4aS)-6-isopropylidene-4,4a-dimethyl-4,5,7,8-tetrahydro-3H-naphthalen-2-one;(4R-CIS)-4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLETHYLIDENE)-2(3H)-NAPHTHALENONE;2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4, 4a-dimethyl-6-(1-methylethylidene)-, (4R-cis)-

Chemical Property of alpha-Vetivone

Chemical Property:

• Vapor Pressure: 0.000154mmHg at 25°C
• Melting Point: 51.5° (Naves, Perrottet); mp of racemate 30-35° (Marshall, Andersen)
• Refractive Index: nD20 1.5384
• Boiling Point: 331.6°Cat760mmHg
• Flash Point: 147.1°C
• PSA: 17.07000
• Density: 0.98g/cm³
• LogP: 4.04830
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 382

Purity/Quality:

99% ^*data from raw suppliers

α-Vetivone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=O)C=C2C1(CC(=C(C)C)CC2)C
• Isomeric SMILES: C[C@@H]1CC(=O)C=C2[C@]1(CC(=C(C)C)CC2)C
• 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.

Technology Process of alpha-Vetivone

There total 23 articles about alpha-Vetivone 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: 81.0%

(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone (72453-44-2) → (4R,4aS)-(+)-4,4a-dimethyl-6-isopropylidene-4,4a,5,6,7,8-hexahydro-(3H)-naphthalen-2-one (15764-04-2,89-89-4)

Guidance literature:

With silica gel; In chloroform; at 60 ℃; for 27h;

DOI:10.1021/jo01292a010

Reference yield:

(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone (72453-44-2) → (4R,4aS)-(+)-4,4a-dimethyl-6-isopropylidene-4,4a,5,6,7,8-hexahydro-(3H)-naphthalen-2-one (15764-04-2,89-89-4) + (+)-nootkatone (4674-50-4)

Guidance literature:

With aluminum oxide; In hexane; at 60 ℃; for 24h;

DOI:10.1021/jo01292a010

Reference yield:

(1R,5S)-(+)-nopinone (38651-65-9) → (4R,4aS)-(+)-4,4a-dimethyl-6-isopropylidene-4,4a,5,6,7,8-hexahydro-(3H)-naphthalen-2-one (15764-04-2,89-89-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / triethylamine / dimethylformamide / 24 h / 95 °C

2: 96 percent / TiCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

3: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating

4: 81 percent / TiCl₄ / CH₂Cl₂

5: 71 percent / NaNH₂ / benzene

6: 1.) O₃; 2.) Zn/CH₃COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.

7: 73 percent / HCl / acetic acid / 21 h / Ambient temperature

8: 81 percent / SiO₂ / CHCl₃ / 27 h / 60 °C

With hydrogenchloride; silica gel; titanium tetrachloride; toluene-4-sulfonic acid; ozone; sodium amide; acetic acid; triethylamine; zinc; In dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo01292a010

upstream raw materials:

(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]

4-isopropylidene-2-methylcyclohexanone

trans-3-penten-2-one

(4R,6R,10S)-4,10-dimethyl-6-(1‘-hydroxyisopropyl)-1-en-3,4,5,6,7,8-hexahydronaphthalen-2-one

Downstream raw materials:

formaldehyd

formic acid

methylammonium carbonate

acetone

Refernces

• 1、 Yanami, Tetsuji,Miyashita, Masaaki,Yoshikoshi, Akira. "Synthetic Study of (+)-Nootkatone from (-)-β-Pinene". . p. 607 - 612. Retrieved 2007/10/02.