(+)-Sativene

Base Information

• Chemical Name: (+)-Sativene
• CAS No.: 3650-28-0
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• DSSTox Substance ID: DTXSID50460872
• Nikkaji Number: J20.776D
• Wikidata: Q76416905
• Mol file: 3650-28-0.mol

Synonyms:(+)-Sativene;3650-28-0;(+)-Sativen;(1R,2S,3S,6S,8S)-6-methyl-7-methylidene-3-propan-2-yltricyclo[4.4.0.02,8]decane;DTXSID50460872;AT14385;XS176154;NS00113755;(+)-Sativene, >=98.0% (sum of enantiomers, GC)

Chemical Property of (+)-Sativene

Chemical Property:

• Vapor Pressure: 0.0254mmHg at 25°C
• Refractive Index: n20/D 1.496
• Boiling Point: 256 °C(lit.)
• Flash Point: 104.9°C
• PSA: 0.00000
• Density: 0.921 g/mL at 20 °C(lit.)
• LogP: 4.27090
• Storage Temp.: 2-8°C
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 301

Purity/Quality:

99% ^*data from raw suppliers

(+)-Sativene ≥98.0% (sum of enantiomers, GC) ^*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: CC(C)C1CCC2(C3C1C(C2=C)CC3)C
• Isomeric SMILES: CC(C)[C@@H]1CC[C@]2([C@H]3[C@@H]1[C@@H](C2=C)CC3)C

Technology Process of (+)-Sativene

There total 60 articles about (+)-Sativene 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%

7-Isopropylidene-4-methyl-8-methylene-octahydro-1,4-methano-indene (159949-84-5) → (+/-)-sativene (3650-28-0,6813-05-4,16641-59-1,22338-87-0,29642-51-1,149884-32-2)

Guidance literature:

With diazene; In dichloromethane; at -10 ℃;

DOI:10.1246/cl.1994.1415

Reference yield: 64.0%

(1RS, 2SR, 3SR, 6SR, 7RS, 8SR)(-3-isopropyl-6-methyltricyclo<4.4.0.02,8>dec-7-yl)methanol (3047-64-1,78086-37-0) → (+/-)-sativene (3650-28-0,6813-05-4,16641-59-1,22338-87-0,29642-51-1,149884-32-2)

Guidance literature:

With pyridine; ortho-nitrophenyl selenocyanate; tributylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; for 16h; Heating;

DOI:10.1016/S0040-4020(01)87392-0

Reference yield: 7.1%

Farnesol (106-28-5) → sativene (3650-28-0,6813-05-4,16641-59-1,22338-87-0,29642-51-1,149884-32-2) + β-cubebene + cubebol + delta-cadinene (483-76-1,13061-82-0,16729-01-4,20085-20-5,60305-17-1,73365-79-4) + germacrene D (23986-74-5) + β-copaene

Guidance literature:

With potassium chloride; In terpene synthase buffer; at 37 ℃; for 18h; pH=8; Enzymatic reaction;

DOI:10.1002/cbic.200900671

upstream raw materials:

Farnesol

((1S,3aR,4S,7S)-7-Isopropyl-4-methyl-octahydro-1,4-methano-inden-8-yl)-methanol

(1RS, 2SR, 3SR, 6SR, 7RS, 8SR)(-3-isopropyl-6-methyltricyclo<4.4.0.0^2,8>dec-7-yl)methanol

7-Isopropylidene-4-methyl-8-methylene-octahydro-1,4-methano-indene

Refernces

• 1、 Lopez-Gallego, Fernando,Agger, Sean A.,Abate-Pella, Daniel,Distefano, Mark D.,Schmidt-Dannert, Claudia. "Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: Catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers". scheme or table. p. 1093 - 1106. Retrieved 2011/03/20.
• 2、 Snowden, Roger L.. "THE INTRAMOLECULAR DIELS-ALDER REACTIONS OF (E)- AND (Z)-METHYL 5--2-PENTENOATE. A STEROSELECTIVE SYNTHESIS OF (+/-)-SATIVENE". . p. 3277 - 3290. Retrieved 2007/10/02.