35628-05-8

Basic information

• Product Name: (S)-(-)-IPSENOL
• Synonyms: (S)-(-)-IPSENOL;(S)-2-Methyl-6-methylene-7-octen-4-ol;(4S)-2-Methyl-6-methylene-7-octen-4-ol;[S,(-)]-2-Methyl-6-methylene-7-octene-4-ol;Isenol;(4S)-(-)-Ipsenol;ipsenol((S)-(-)-IPSENOL );2-Methyl-6-methylene-7-octen-4-ol
• CAS NO: 35628-05-8
• Molecular Formula: C10H18O
• Molecular Weight: 154.25
• Mol File: 35628-05-8.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 222.2 °C at 760 mmHg
• Flash Point: 83.4 °C
• Appearance: /
• Density: 0.848 g/cm³
• Vapor Pressure: 0.0211mmHg at 25°C
• Refractive Index: 1.452
• PKA: 15.04±0.20(Predicted)
• CAS DataBase Reference: (S)-(-)-IPSENOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-IPSENOL(35628-05-8)
• EPA Substance Registry System: (S)-(-)-IPSENOL(35628-05-8)

Safety Data

• Hazardous Substances Data: 35628-05-8(Hazardous Substances Data)

Usage

Uses

Ipsenol is a pheromone of pine bark beetles.

Synthesis Reference(s)

Journal of the American Chemical Society, 101, p. 3340, 1979 DOI: 10.1021/ja00506a034The Journal of Organic Chemistry, 48, p. 3122, 1983 DOI: 10.1021/jo00166a044Tetrahedron Letters, 16, p. 3047, 1975

InChI:InChI=1/C10H18O/c1-5-9(4)7-10(11)6-8(2)3/h5,8,10-11H,1,4,6-7H2,2-3H3/t10-/m0/s1

Upstream product

• 57566-86-6 (2Ξ,4S)-4-hydroxy-6-methyl-2-(phenylselanyl-methyl)-heptanal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 57566-85-5 (S)-γ-isobutyl-α-methylene-γ-butyrolactone 
• 19493-09-5 Methylenetriphenylphosphorane 
• 590-86-3 isovaleraldehyde 
• 1335316-66-9 4,4,5,5-tetramethyl-2-(2-methylenebut-3-enyl)-1,3,2-dioxaborolane 
• 57566-87-7 (S)-5-Isobutyl-3-phenylselanylmethyl-dihydro-furan-2-one 
• 144069-35-2 2,2-Dimethyl-propionic acid (1S,4S)-4-hydroxy-1,6-dimethyl-2-oxo-heptyl ester 
• 261379-31-1 (S)-4-Hydroxy-6-methyl-2-methylene-heptanoic acid methyl ester 
• 331970-29-7 trifluoro-methanesulfonic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-vinyl ester 
• 331993-83-0 (4S)-4-hydroxy-6-methylheptan-2-one 
• 423774-49-6 Trimethyl-((S)-6-methyl-4-vinyloxy-hept-1-ynyl)-silane 
• 423774-48-5 (S)-6-Methyl-1-trimethylsilanyl-hept-1-yn-4-ol 
• 423774-50-9 (S)-2-Methyl-6-[1-trimethylsilanyl-meth-(E)-ylidene]-oct-7-en-4-ol 

Relevant articles and documents

A simple synthesis of (-)-(R)-ipsdienol and (-)-(S)-ipsenol

A short and efficient synthesis of the unnatural enantiomer of (+)-(S)- ipsdienol 1 and (-)-(S)-ipsenol 2 is presented via an asymmetric allylboration. The synthesis was achieved by using a one-pot reduction- methylenation of an exo-methylene lactone intermediate. (C) 1999 Elsevier Science Ltd.

A synthesis of S-(-)-ipsenol from lactic acid

A six step synthesis of S-(-)-ipsenol, a constituent of the sex pheromone of the bark beetle, from lactic acid employs an asymmetric aldol condensation and a novel molybdenum catalyzed elimination of an allyl ester as key steps.

Enantioselective Isoprenylboration Reaction of Aldehydes Catalyzed by a Chiral Phosphoric Acid

The BINOL-derived chiral phosphoric acid (R)-TRIP is utilized as an organocatalyst in the asymmetric isoprenylboration reaction of aldehydes, wherein hydrogen-bond interactions play a key role in the control of enantioselectivity. A wide arrays of enantioenriched dienyl homoallyl alcohols, including two natural products (?)-Ipsdienol and (?)-Ipsenol, have been successfully constituted. The synthetic application to chiral isoprenylated isobenzofuranone, vinyloxirane and cyclohexene derivatives has also been disclosed. (Figure presented.).

Proline-catalyzed asymmetric aldol reactions between ketones and alpha-unsubstituted aldehydes.

[reaction: see text] With this communication we extend the methodology of proline-catalyzed direct asymmetric aldol reactions to include alpha-unsubstituted aldehydes as acceptors. This important aldehyde class gives the corresponding aldols in 22-77% yield and up to 95% ee when the reactions are performed in pure acetone or in ketone/chloroform mixtures. On the basis of these results we have developed a concise new synthesis of (S)-ipsenol.