Ipsenol

Base Information

• Chemical Name: Ipsenol
• CAS No.: 35628-05-8
• Deprecated CAS: 6994-88-3
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.252
• Hs Code.: 2905290000
• European Community (EC) Number: 889-813-7
• UNII: 02H2YW09TH
• DSSTox Substance ID: DTXSID10885628
• Nikkaji Number: J19.908G
• Wikidata: Q27231522
• Metabolomics Workbench ID: 28027
• Mol file: 35628-05-8.mol

Synonyms:(S)-ipsenol;ipsenol

Chemical Property of Ipsenol

Chemical Property:

• Vapor Pressure: 0.0211mmHg at 25°C
• Refractive Index: 1.452
• Boiling Point: 222.2 °C at 760 mmHg
• PKA: 15.04±0.20(Predicted)
• Flash Point: 83.4 °C
• PSA: 20.23000
• Density: 0.848 g/cm³
• LogP: 2.52570
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

(S)-Ipsenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(CC(=C)C=C)O
• Isomeric SMILES: CC(C)C[C@@H](CC(=C)C=C)O
• Uses: Ipsenol is a pheromone of pine bark beetles.

Technology Process of Ipsenol

There total 41 articles about Ipsenol 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: 99.0%

2-(4-methyl-1-(2-tetrahydropyranyloxy)pentyl)-1,3-butadiene → (S)-ipsenol (35628-05-8,6994-88-3)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 1h; Ambient temperature;

DOI:10.1021/ja00263a020

Reference yield: 90.0%

(2'S)-2-<2'<(tert-butyl)dimethylsilyloxy>-4'-methylpentyl>buta-1,3-diene (129084-78-2) → (S)-ipsenol (35628-05-8,6994-88-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/ol006976y

Reference yield: 77.0%

isovaleraldehyde (590-86-3) + tributyl(2-methylene-but-3-enyl)stannane → (S)-ipsenol (35628-05-8,6994-88-3)

Guidance literature:

With titanium(IV) isopropylate; (i-C₃H₇)SB(C₂H₅)2; (R)-1,1'-Bi-2-naphthol; In various solvent(s); at -20 ℃; for 5h;

DOI:10.1002/1099-0690(200103)2001:6<1143::aid-ejoc1143>3.0.co;2-o

upstream raw materials:

(S)-2-isobutyloxirane

1,3-butadien-2-ylmagnesium chloride

(2Ξ,4S)-4-hydroxy-6-methyl-2-(phenylselanyl-methyl)-heptanal

Methyltriphenylphosphonium bromide

Refernces

• 1、 Oertle, Konrad,Beyeler, Harry,Duthaler, Rudolf O.,Lottenbach, Willi,Riediker, Martin,Steiner, Eginhard. "A Facile Synthesis of Optically Pure (-)-(S)-Ipsenol Using a Chiral Titanium Complex". . p. 353 - 358. Retrieved 1990.
• 2、 Nakajima, Ryota,Urabe, Hirokazu,Sato, Fumie. "Intramolecular coupling of vinyl ether and olefins or acetylenes with Ti(II) reagent. Regio- and stereo-selective vinyltitanation of carbon-carbon multiple bonds". . p. 4 - 5. Retrieved 2002.
• 3、 -. "METHOD FOR PRODUCING MONOTERPENE AND MONOTERPINOID COMPOUNDS AND USE THEREOF". Page/Page column 2; 4; 5. . Retrieved 2012/05/07.