(+)-alpha-Santalene

Base Information

• Chemical Name: (+)-alpha-Santalene
• CAS No.: 27353-28-2
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• UNII: ULF48AV46L,NG8A32XKW3
• Metabolomics Workbench ID: 61765
• Wikidata: Q27131275
• Mol file: 27353-28-2.mol

Synonyms:(+)-alpha-santalene;ent-Santalene;D-alpha-Santalene;ULF48AV46L;alpha-Santalene, (+)-;UNII-ULF48AV46L;22527-23-7;(+)-1,7-Dimethyl-7-(4-methyl-3-penten-1-yl)tricyclo(2.2.1.02,6)heptane;Tricyclo(2.2.1.02,6)heptane, 1,7-dimethyl-7-(4-methyl-3-penten-1-yl)-, (+)-;(1S,2R,4S,6R,7R)-1,7-dimethyl-7-(4-methylpent-3-en-1-yl)tricyclo[2.2.1.0(2,6)]heptane;D-.ALPHA.-SANTALENE;(+)-.ALPHA.-SANTALENE;CHEBI:61677;KWFJIXPIFLVMPM-PEGGXJLSSA-N;(+/-)-.ALPHA.-SANTALENE;.ALPHA.-SANTALENE, (+)-;.ALPHA.-SANTALENE, (+/-)-;Q27131275;(2R,6S,7R)-1,7-dimethyl-7-(4-methylpent-3-enyl)tricyclo[2.2.1.02,6]heptane;1,7-DIMETHYL-7-(4-METHYL-3-PENTENYL)TRICYCLO(2.2.1.0(2,6))HEPTANE

Chemical Property of (+)-alpha-Santalene

Chemical Property:

• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 309

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCCC1(C2CC3C1(C3C2)C)C)C
• Isomeric SMILES: CC(=CCC[C@@]1(C2C[C@H]3C1([C@H]3C2)C)C)C

Technology Process of (+)-alpha-Santalene

There total 25 articles about (+)-alpha-Santalene 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: 64.0%

8-bromotricyclene (52645-83-7,95910-71-7) + 3-Methyl-1-butene (563-45-1) → (-)-1,7-dimethyl-7-(4-methyl-3-pentenyl)tricyclo[2.2.1.0(2,6)]heptane (512-61-8,22527-23-7,27353-28-2)

Guidance literature:

With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; at -75 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)73929-3

Reference yield:

ethyl 3-(anti-1,7-dimethyl-2-(acetylamino)bicyclo<2.2.1>hept-7-yl)propanoate (73838-28-5,73855-15-9) → (-)-1,7-dimethyl-7-(4-methyl-3-pentenyl)tricyclo[2.2.1.0(2,6)]heptane (512-61-8,22527-23-7,27353-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: p-toluenesulfonyl chloride / pyridine / 19 h / Heating

2: 0.14 g / diisobutylaluminum hydride / toluene / 3.5 h / -78 °C

3: 1) n-BuLi / 1) DME/hexane, 0 deg C, 10 min., 2) DME, 17h

With n-butyllithium; diisobutylaluminium hydride; p-toluenesulfonyl chloride; In pyridine; toluene;

DOI:10.1021/jo01303a026

Reference yield:

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → (-)-1,7-dimethyl-7-(4-methyl-3-pentenyl)tricyclo[2.2.1.0(2,6)]heptane (512-61-8,22527-23-7,27353-28-2)

Guidance literature:

With santalene synthase from Santalumspicatum; In aq. buffer; at 25 ℃; for 12h; pH=7.5; Enzymatic reaction;

DOI:10.1021/acschembio.5b00539

upstream raw materials:

3-(2,3-dimethyl-2,6-cyclo-norbornan-3-yl)-propionaldehyde

isopropyltriphenylphosphonium iodide

8-bromotricyclene

3-Methyl-1-butene

Downstream raw materials:

cis-α-santalol

(1S,2R,4R)-2-Methyl-3-methylene-2-(4-methyl-pent-3-enyl)-bicyclo[2.2.1]heptane

(E)-5-(2,3-dimethyltricyclo<2.2.1.0^2,6>hept-3-yl)-2-methylpent-2-enal