(+)-Aromadendrene

Base Information

• Chemical Name: (+)-Aromadendrene
• CAS No.: 489-39-4
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• European Community (EC) Number: 207-694-6
• DSSTox Substance ID: DTXSID60862020,DTXSID80881253
• Nikkaji Number: J12.596B
• Wikidata: Q76416625
• Metabolomics Workbench ID: 127658
• ChEMBL ID: CHEMBL2269083
• Mol file: 489-39-4.mol

Synonyms:aromadendrene

Chemical Property of (+)-Aromadendrene

Chemical Property:

• Melting Point: 262°C
• Refractive Index: n20/D 1.497
• Boiling Point: 261-263 °C(lit.)
• Flash Point: 106.5°C
• PSA: 0.00000
• Density: 0.93g/cm³
• LogP: 4.27090
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Soluble), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 299

Purity/Quality:

98% min ^*data from raw suppliers

(+)-Aromadendrene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2C1C3C(C3(C)C)CCC2=C
• Isomeric SMILES: C[C@@H]1CC[C@@H]2[C@@H]1[C@H]3[C@H](C3(C)C)CCC2=C
• Uses: (+)-Aromadendrene may be used as a chiral starting material to synthesize other sesquiterenes such as (-)-apoaromadendrone, (-)-kessane, (+)-spathulenol, (+)-ledene and (-)-isoledene.

Technology Process of (+)-Aromadendrene

There total 23 articles about (+)-Aromadendrene 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: 89.0%

Methanesulfonic acid (1aR,4S,4aR,7R,7aR,7bS)-1,1,7-trimethyl-decahydro-cyclopropa[e]azulen-4-ylmethyl ester (175985-51-0) → (+)-aromadendrene (489-39-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 100 ℃; for 18h;

DOI:10.1016/0040-4020(96)00086-5

Reference yield: 60.0%

(1aR,4aR,7R,7aS,7bS)-1,1,7-Trimethyldecahydro-4H-cyclopropa[e]azulen-4-one (99147-41-8) + Methyltriphenylphosphonium bromide (1779-49-3) → (+)-aromadendrene (489-39-4)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 0.166667h; Inert atmosphere;

(1aR,4aR,7R,7aS,7bS)-1,1,7-Trimethyldecahydro-4H-cyclopropa[e]azulen-4-one; In tetrahydrofuran; at -78 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.08.079

Reference yield:

methyl (+)-(1S,7R)-8,8-dimethyl-3-oxobicyclo<5.1.0>octane-4-carboxylate (176199-11-4) → (+)-aromadendrene (489-39-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 100 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

2: imidazole / dimethylformamide / 12 h / Ambient temperature

3: 90 percent / Ley's tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide, molecular sieves / CH₂Cl₂ / 0.25 h / Ambient temperature

4: 1.) LDA, HMPA / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to RT, 4 h

5: 96 percent / PdCl₂, CuCl, air / dimethylformamide; H₂O / 4.5 h / Ambient temperature

6: 84 percent / NaHMDS, HMPA / tetrahydrofuran / 0.67 h / -78 - -50 °C / a) -78 deg C_. 15 min, b) 0 deg C, 15 min, c) 50 deg C, 10 min

7: 1.) lithium hexamethyldisilazane, HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT, 2 h

8: 86 percent / lithium tetramethyldisilazane, HMPA / tetrahydrofuran / 2 h / -78 - 20 °C

9: 93 percent / H₂ / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature

10: NaBH₄ / methanol / 2 h / Ambient temperature

11: pyridine, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

12: 68 percent / n-Bu₃SnH, AIBN / toluene / 3 h / Heating

13: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

14: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 0 °C

15: 89 percent / DBU / toluene / 18 h / 100 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; molecular sieve; tetrapropylammonium perruthennate; air; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium bis(dimethylsilyl)amide; copper(l) chloride; palladium dichloride; lithium hexamethyldisilazane; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0040-4020(96)00086-5

upstream raw materials:

(-)-globulol

Methanesulfonic acid (1aR,4S,4aR,7R,7aR,7bS)-1,1,7-trimethyl-decahydro-cyclopropa[e]azulen-4-ylmethyl ester

methyl (+)-(1S,7R)-8,8-dimethyl-3-oxobicyclo<5.1.0>octane-4-carboxylate

(+)-(1S,2S,4R,7R)-4-tert-butyldimethylsiloxymethyl-8,8-dimethyl-2-(2-propenyl)bicyclo<5.1.0>octan-3-one

Downstream raw materials:

C₂₁H₃₀OSe

C₂₁H₃₀OSe

[1R-(1α,3aβ,4α,7β)]-1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene

Toluene-4-sulfonic acid (1aR,4R,4aR,7R,7aS,7bS)-4-hydroxy-1,1,7-trimethyl-decahydro-cyclopropa[e]azulen-4-ylmethyl ester

Refernces

• 1、 Duhamel, Nina,Martin, Damian,Larcher, Roberto,Fedrizzi, Bruno,Barker, David. "Convenient synthesis of deuterium labelled sesquiterpenes". supporting information. p. 4496 - 4499. Retrieved 2016/09/14.
• 2、 Gijsen, Henricus J. M.,Kanai, Karoly,Stork, Gerrit A.,Wijnberg, Joannes B.P.A.,Orru, Romano V. A.,Seelen, Claudy G. J. M.,Van Der Kerk, Sies M.,De Groot, Aede. "The conversion of natural (+)-aromadendrene into chiral synthons-I". . p. 7237 - 7246. Retrieved 2007/10/02.