(+)-Verbenone

Base Information

• Chemical Name: (+)-Verbenone
• CAS No.: 18309-32-5
• Molecular Formula: C10H14 O
• Molecular Weight: 150.221
• European Community (EC) Number: 242-195-7
• NSC Number: 36846
• UNII: 99S17893UW,IFV46DXC6U
• DSSTox Substance ID: DTXSID30885024
• Nikkaji Number: J53.851E
• Wikipedia: Verbenone
• Wikidata: Q55929359
• Metabolomics Workbench ID: 155637
• ChEMBL ID: CHEMBL1409937
• Mol file: 18309-32-5.mol

Synonyms:verbenone;verbenone, (+-)-isomer;verbenone, (1R)-isomer;verbenone, (1S)-isomer

Chemical Property of (+)-Verbenone

Chemical Property:

• Melting Point: 6.5°
• Refractive Index: nD18 1.4957
• Boiling Point: 227.5°Cat760mmHg
• Flash Point: 85°C
• PSA: 17.07000
• Density: 0.992g/cm³
• LogP: 2.17770
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 150.104465066
• Heavy Atom Count: 11
• Complexity: 248

Purity/Quality:

99% ^*data from raw suppliers

Verbenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C2CC1C2(C)C
• Isomeric SMILES: CC1=CC(=O)[C@@H]2C[C@H]1C2(C)C

Technology Process of (+)-Verbenone

There total 54 articles about (+)-Verbenone 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: 78.0%

(1R,3R,4S,5R,SS)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one (214827-18-6) → Verbenone (18309-32-5)

Guidance literature:

With potassium carbonate; In toluene; at 95 ℃; for 48h;

DOI:10.1021/jo9807316

Reference yield: 72.0%

(1R,3R,4S,5R)-3-Benzenesulfinyl-4,6,6-trimethyl-bicyclo[3.1.1]heptan-2-one → Verbenone (18309-32-5)

Guidance literature:

With potassium carbonate; In toluene; at 95 ℃; for 48h;

DOI:10.1021/jo9807316

Reference yield: 67.0%

(+)-α-pinene (7785-70-8,25766-18-1) → Verbenone (18309-32-5)

Guidance literature:

With pyridine; tert.-butylhydroperoxide; N-hydroxy-3,4,5,6-tetrachlorophthalimide; lithium perchlorate; In acetonitrile; chemoselective reaction; Electrochemical reaction;

DOI:10.1038/nature17431

upstream raw materials:

(+)-α-pinene

(+)-trans-verbenol

trans-pin-3-en-2-ol

(+)-cis-verbenol

Downstream raw materials:

(+)-cis-pinononoic acid

(1R,5S)-3-[2-(2-Bromo-phenyl)-allyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-3-en-2-one

2-hydroxy-1-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]ethanone

(1S,2S,6R)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol