(+)-Thujopsene

Base Information

• Chemical Name: (+)-Thujopsene
• CAS No.: 470-40-6
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• European Community (EC) Number: 207-426-8
• DSSTox Substance ID: DTXSID50881245
• Metabolomics Workbench ID: 61801
• Wikidata: Q27131354
• Wikipedia: Thujopsene
• Mol file: 470-40-6.mol

Synonyms:(+)-thujopsene;cis-Thujopsene;470-40-6;(1aR,4aR,8aR)-2,4a,8,8-tetramethyl-1,1a,4,4a,5,6,7,8-octahydrocyclopropa[d]naphthalene;CHEBI:61737;DTXSID50881245;Cyclopropa(D)Naphthalene, 1,1A,4,4A,5,6,7,8-Octahydro-2,4A,8,8-Tetramethyl-, (1As,4As,8As);C20724;Q27131354;(1S,6S,10S)-2,2,6,9-Tetramethyltricyclo[8.1.0.01.6]undec-8-ene;(1aR,4aR,81R)-2,4a,8,8-tetramethyl-1,1a,4,4a,5,6,7,8-octahydrocyclopropa[d]naphthalene

Chemical Property of (+)-Thujopsene

Chemical Property:

• Melting Point: <25 °C
• Refractive Index: n20/D 1.505
• Boiling Point: 256.5°Cat760mmHg
• Flash Point: 105.9°C
• PSA: 0.00000
• Density: 0.95g/cm³
• LogP: 4.55910
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Sparingly), Dichloromethane (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 336

Purity/Quality:

99%min ^*data from raw suppliers

(?)-Thujopsene ≥97.0% (GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC2(CCCC(C23C1C3)(C)C)C
• Isomeric SMILES: CC1=CC[C@]2(CCCC([C@@]23[C@@H]1C3)(C)C)C
• Uses: (-)-Thujopsene is an essential oil.

Technology Process of (+)-Thujopsene

There total 10 articles about (+)-Thujopsene 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: 100.0%

4-methoxy-4,7,11,11-tetramethyltricyclo[5.4.0.01,3]undecane → thujopsene (470-40-6)

Guidance literature:

With silica gel; Product distribution;

DOI:10.1023/A:1012328407347

Reference yield:

(+)-mayurone (4677-90-1) → thujopsene (470-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / Pd-C / methanol / 0.13 h

2: 1) Mg / 1) Et₂O, 2) 0 deg C, 1 d

With hydrogen; magnesium; palladium on activated charcoal; In methanol;

DOI:10.1016/0031-9422(93)85295-3

Reference yield:

thujopsane-7β-ol (150737-93-2) → thujopsene (470-40-6)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 20 ℃; for 1.5h;

DOI:10.1016/S0040-4020(99)00476-7

upstream raw materials:

methylmagnesium bromide

dihydromayurone

(-)-thujopsan-2α-ol

(+)-dihydromayurone

Downstream raw materials:

widdrol

1,4,11,11-tetramethylbicyclo[5.4.0]undeca-3,7-diene

cuparene

β-chamigrene

Refernces

• 1、 Yarovaya,Polovinka,Korchagina,Gatilov,Bagryanskaya,Shcherbukhin,Shal'ko,Zenkovets,Barkhash. "Acid-catalyzed rearrangements of (-)-thujopsene". . p. 362 - 374. Retrieved 2007/10/03.
• 2、 Johnson, Carl R.,Barbachyn, Michael R.. "β-Hydroxysulfoximine-Directed Simmons-Smith Cyclopropanations. Synthesis of (-)- and (+)-Thujopsene". . p. 4290 - 4291. Retrieved 2007/10/02.