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

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

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 
• 129084-78-2 (2'S)-2-<2'<(tert-butyl)dimethylsilyloxy>-4'-methylpentyl>buta-1,3-diene 
• 57566-85-5 (S)-γ-isobutyl-α-methylene-γ-butyrolactone 
• 19493-09-5 Methylenetriphenylphosphorane 
• 423774-50-9 (S)-2-Methyl-6-[1-trimethylsilanyl-meth-(E)-ylidene]-oct-7-en-4-ol 
• 62961-64-2 D-(-)-diisopropyl tartrate 
• 122038-72-6 dimethoxyisoprenylborane 
• 590-86-3 isovaleraldehyde 
• 128291-26-9 B-isoprenyldiisopinocampheylborane 
• 128291-28-1 2'-isopropenylpotassium 
• 143998-50-9 2,2-Dimethyl-propionic acid (1S,4S)-4-hydroxy-1,6-dimethyl-2-methylene-heptyl ester 
• 920-39-8 isopropylmagnesium bromide 
• 129100-78-3 (2-Methylene-3-buten-1-yl)oxirane 

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 Facile Synthesis of Optically Pure (-)-(S)-Ipsenol Using a Chiral Titanium Complex

A stereocontrolled synthetic route to optically pure (-)-(S)-ipsenol (I), the pheromone of Pityokteines curvidens and various other bark-beetle species is described.Key step of the synthesis is an enantioselective aldol reaction using a chiral titanium-carbohydrate complex (Scheme 1).The carboxylate function of the optically pure β-hydroxy acid 5 thus obtained in mol quantities is then elaborated to the diene moiety by standard methodology (Scheme 2).

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.

Intramolecular coupling of vinyl ether and olefins or acetylenes with Ti(II) reagent. Regio- and stereo-selective vinyltitanation of carbon-carbon multiple bonds

Treatment of m-alkenyl (or m-alkynyl) vinyl ethers (m = 3,4) with a Ti(II) reagent generated most likely bicyclic oxatitana-cycles, which eliminate the alkoxide tether to effect the selective vinyltitanation of the alkene or alkyne moiety to give m-vinyl-

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.).

METHOD FOR PRODUCING MONOTERPENE AND MONOTERPINOID COMPOUNDS AND USE THEREOF

In various embodiments, the present disclosure provides a method and enzyme for forming various compounds, such as monoterpenes and monoterpenoid compounds. In a specific example, the present disclosure provides a method for producing one or more of (?)-ipsdienol, (?)-ipsenol, ipsenone, and ipsdienone. The present disclosure also provides methods of using compounds formed from the disclosed method and enzyme.

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.

Catalytic asymmetric allylic transfer reactions for the Enantioselective synthesis of dienyl and enynyl alcohols

Efficient catalytic asymmetric allylic transfer reactions of achiral aldehydes with 2-ethynyl- and 2-ethenyl-2-propenyl-stannane promoted by BINOL-TiIV complex with synergetic reagent are achieved for the synthesis of homoenynyl- and dienyl alcohols with high levels of enantioselectivity. The range of enantioselectivity is 84-99% ee with good chemical yields. The application of catalytic asymmetric dienylation in a single operation was exemplified by the enantioselective synthesis of naturally occurring (-)-Ipsdienol and (-)-Ipsenol.

Enantioselective synthesis of ipsenol and ipsdienol using a (2-bromoallyl)borane derivative

(S)-(-)-Ipsenol and (S)-(+)-ipsdienol, a major component of the sex pheromone of the bark beetle, and their enantiomers were prepared enantioselectively using tartrate esters of (2-bromoallyl)boronic acid in the key step.

Optically active allylic tin reagent as an enantio-divergent synthon of isoprenoids via remote and divergent asymmetric induction

(S)-2-(1-Hydroxymethyl)allyltin (1a) can be prepared in high enantiomeric purity. When its methylated and acetylated derivatives are allowed to add to aldehydes with the help of i-PrOTiCl3 and SnCl4, syn- and anti-homoallylic alcohol