alpha-Santalene

Base Information

• Chemical Name: alpha-Santalene
• CAS No.: 512-61-8
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• DSSTox Substance ID: DTXSID60862085
• Nikkaji Number: J13.994G,J508.347H
• Wikidata: Q29529955
• Mol file: 512-61-8.mol

Synonyms:alpha-santalene;beta-santalene

Chemical Property of alpha-Santalene

Chemical Property:

• Vapor Pressure: 0.04mmHg at 25°C
• Boiling Point: 247.6°C at 760 mmHg
• Flash Point: 73.8°C
• Density: 0.944g/cm³
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• 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:

99%, ^*data from raw suppliers

(-)-α-Santalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCCC1(C2CC3C1(C3C2)C)C)C
• Uses: (-)-α-Santalene, is a component found in East Indian sandalwood oil. It can also be found in citrus essential oils.

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

Refernces

• 1、 Schlosser, Manfred,Zhong, Guo-Fu. "A shortcut to α-Santalol". . p. 5441 - 5444. Retrieved 2007/10/02.
• 2、 Christenson, Philip A.,Willis, Brian J.. "East Indian Sandalwood Oil. 2. Stereoselective Synthesis of (+/-)-Epi-β-santalene and (+/-)-Epi-β-santalol". . p. 3068 - 3072. Retrieved 2007/10/02.