35628-00-3

Basic information

• Product Name: IPSDIENOL
• Synonyms: 2,7-Octadien-4-ol, 2-methyl-6-methylene-, (4S)-;2,7-Octadien-4-ol, 2-methyl-6-methylene-, (S)-;2-Methyl-6-methylene-2,7-octadien-4-ol;IPSDIENOL;(S)-(+)-IPSDIENOL;(S)-2-Methyl-6-methylene-2,7-octadien-4-ol;(4S)-2-Methyl-6-methylene-2,7-octadien-4-ol;(S)-2-methyl-6-methyleneocta-2,7-dien-4-ol
• CAS NO: 35628-00-3
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• Mol File: 35628-00-3.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 233.6 °C at 760 mmHg
• Flash Point: 92.2 °C
• Appearance: /
• Density: 0.87 g/cm³
• Vapor Pressure: 0.0103mmHg at 25°C
• Refractive Index: 1.473
• Storage Temp.: 2-8°C
• PKA: 14?+-.0.20(Predicted)
• CAS DataBase Reference: IPSDIENOL(CAS DataBase Reference)
• NIST Chemistry Reference: IPSDIENOL(35628-00-3)
• EPA Substance Registry System: IPSDIENOL(35628-00-3)

Safety Data

• Hazardous Substances Data: 35628-00-3(Hazardous Substances Data)

Usage

Description

IPSDIENOL, also known as S-Ipsdienol, is a terpene compound that serves as a conspecific aggregation pheromone for the Asian larch bark beetle, Ips subelongatus. It is recognized for its potential applications in various industries due to its antioxidant and antimicrobial properties.

Uses

Used in Food Industry:
IPSDIENOL is used as an antioxidant and antimicrobial agent for preserving the quality and freshness of food products, as well as enhancing their shelf life.
Used in Pharmaceutical Industry:
IPSDIENOL is used as an antioxidant and antimicrobial agent for the development of drugs and medications, contributing to the improvement of their efficacy and stability.
Used in Pesticide Industry:
IPSDIENOL is used as an active ingredient in the formulation of pesticides, specifically targeting the Asian larch bark beetle, Ips subelongatus, to control their population and protect the affected trees and plants.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 3122, 1983 DOI: 10.1021/jo00166a044Tetrahedron Letters, 26, p. 2797, 1985 DOI: 10.1016/S0040-4039(00)94915-3

InChI:InChI=1/C10H16O/c1-5-9(4)7-10(11)6-8(2)3/h5-6,10-11H,1,4,7H2,2-3H3/t10-/m1/s1

Synthetic route

(S)-4-t-Butyldimethylsilyloxy-2-methyl-6-methyleneocta-2,7-diene (134393-22-9) → (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;	92%

3,3-dimethyl acrylaldehyde (107-86-8) + tert-butyl (2-methylenebut-3-en-1-yl) carbonate → (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Conditions	Yield
With potassium phosphate; C56H51IrN2O10P2 In 1,2-dimethoxyethane; isopropyl alcohol at 70℃; for 24h; Inert atmosphere; Sealed tube; enantioselective reaction;	71%

tert-butyl (2-methylenebut-3-en-1-yl) carbonate + 3-methyl-2-buten-1-ol (556-82-1) → (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Conditions	Yield
With potassium phosphate; C56H51IrN2O10P2 In 1,2-dimethoxyethane at 70℃; for 24h; Inert atmosphere; Sealed tube; enantioselective reaction;	64%

2-[(4S)-8-chloro-2-methyl-6-methylideneoct-2-en-4-yloxycarbonyl]benzoic acid (1408287-41-1) → (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Conditions	Yield
With potassium tert-butylate; tert-butyl alcohol for 1h; Inert atmosphere; Reflux;	55%

(R)-5-acetoxy-7-methyl-3-methylene-octa-1,6-diene (72496-38-9) → (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

(-)-(1S,4S,5S)-2(10)-pinen-4-ol (64243-10-3) → (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Conditions	Yield
at 550℃; under 0.01 Torr;

L-(+)-diisopropyl tartrate (2217-15-4) + 3,3-dimethyl acrylaldehyde (107-86-8) + dimethoxyisoprenylborane (122038-72-6) → (R)-(-)-2-Methyl-6-methylene-2,7-octadien-4-ol (60894-97-5) + (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Conditions	Yield
2.) toluene, -75 deg C, 1h; warm to room temperature; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

Upstream product

• 72496-38-9 (R)-5-acetoxy-7-methyl-3-methylene-octa-1,6-diene 
• 64243-10-3 (-)-(1S,4S,5S)-2⁽¹⁰⁾-pinen-4-ol 
• 2217-15-4 L-(+)-diisopropyl tartrate 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 122038-72-6 dimethoxyisoprenylborane 
• 128291-28-1 2'-isopropenylpotassium 
• 128291-26-9 B-isoprenyldiisopinocampheylborane 
• 539-70-8 2-Methyl-6-methylene-2,7-octadien-4-one 
• 134393-22-9 (S)-4-t-Butyldimethylsilyloxy-2-methyl-6-methyleneocta-2,7-diene 
• 1826-67-1 vinyl magnesium bromide 
• 6994-89-4 (E)-2-methyl-6-methylene-3,7-octadiene-2-ol 
• 134393-17-2 (S)-Methyl 2-Hydroxy-4-methylene-5-hexenoate 
• 134393-20-7 (S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methylene-hex-5-enal 
• 134393-19-4 (S)-Methyl 2-t-Butyldimethylsilyloxy-4-methylene-5-hexenoate 

Relevant articles and documents

Enantioselective iridium-catalyzed carbonyl isoprenylation: Via alcohol-mediated hydrogen transfer

Highly enantioselective iridium catalyzed carbonyl (2-vinyl)allylation or "isoprenylation" is achieved via hydrogen auto-transfer or 2-propanol-mediated reductive coupling from primary alcohol or aldehyde reactants, respectively. Using this method, asymmetric total syntheses of the terpenoid natural products (+)-ipsenol and (+)-ipsdienol were achieved.

A new synthesis of the enantiomers of ipsdienol, the pheromone of the Ips bark beetles

The enantiomers (~96% e.e.) of ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol, 1a) were synthesized from the enantiomers of serine (5) in 16-21% overall yield in 8 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.).

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.