(+)-Calamenene

Base Information

• Chemical Name: (+)-Calamenene
• CAS No.: 22339-23-7
• Molecular Formula: C₁₅H₂₂
• Molecular Weight: 202.34
• UNII: BP6FM49LSX
• Nikkaji Number: J16.301E
• Wikidata: Q105208666
• Mol file: 22339-23-7.mol

Synonyms:(7R,10R)-calamenene;calamenene

Chemical Property of (+)-Calamenene

Chemical Property:

• Vapor Pressure: 0.00495mmHg at 25°C
• Boiling Point: 285°Cat760mmHg
• Flash Point: 125.4°C
• PSA: 0.00000
• Density: 0.9g/cm³
• LogP: 4.63190
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 202.172150702
• Heavy Atom Count: 15
• Complexity: 206

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C2=C1C=CC(=C2)C)C(C)C
• Isomeric SMILES: C[C@@H]1CC[C@@H](C2=C1C=CC(=C2)C)C(C)C

Technology Process of (+)-Calamenene

There total 15 articles about (+)-Calamenene 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:

(1R,4R)-1,2,3,4,5,6-hexahydro-1,6-dimethyl-4-(1-methylethyl)naphthalene → cis-(+)-calamenene (22339-23-7)

Guidance literature:

With air; In chloroform; at 20 ℃; for 168h;

DOI:10.1016/S0031-9422(99)00123-5

Reference yield:

(+)-10β(H)-muurola-3,7,(11)-dien-1-ol → (7S,10R)-trans-calamenene (35943-92-1) + cis-(+)-calamenene (22339-23-7)

Guidance literature:

With Amberlyst 15; In hexane; at 20 ℃; for 48h;

DOI:10.1016/S0031-9422(99)00321-0

Reference yield:

2,15-dihydroxycalamenene (874657-05-3) → cis-(+)-calamenene (22339-23-7)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd/C / methanol

2: NaH; aq. NH₄Cl / tetrahydrofuran / 20 °C

3: Li; liq. NH₃; NH₄Cl / -60 °C

With ammonia; hydrogen; lithium; sodium hydride; ammonium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/j.tetlet.2005.05.037

upstream raw materials:

(8R,8aS)-5-Isopropyl-3,8-dimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-2-ol

(1S,4R)-1-Isopropyl-4,7-dimethyl-5-methylsulfanyl-1,2,3,4-tetrahydro-naphthalene

2,15-dihydroxycalamenene

(5R,8R)-4-Hydroxy-8-isopropyl-5-methyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester

Downstream raw materials:

cadalenequinone mono 2,4-dinitrophenylhydrazone

Refernces

• 1、 Serra, Stefano,Fuganti, Claudio. "Aromatic annulation on the p-menthane monoterpenes: Enantiospecific synthesis of the trans and cis isomers of calamenene and 8-hydroxycalamenene". . p. 4769 - 4772. Retrieved 2007/10/03.
• 2、 Weyerstahl, Peter,Wahlburg, Hans-Christian,Marschall, Helga,Rustaiyan, Abdolhossein. "New Cadinene and Bisabolene Derivatives from the Essential Oil of Pulicaria gnaphalodes". . p. 1117 - 1124. Retrieved 2007/10/02.