51911-82-1

Usage

Uses

Used in Plant Defense Mechanisms:
4,8-Dimethylnona-1,3,7-triene is used as a signaling molecule for [plant defense activation] because it is released when plants are damaged or under stress, alerting nearby plants to activate their own defense mechanisms.
Used in Agriculture:
4,8-Dimethylnona-1,3,7-triene is used as a natural pest control agent for [attracting insect predators] due to its ability to attract certain insects, particularly predators of herbivores that are feeding on the plant.
Used in Antimicrobial Applications:
4,8-Dimethylnona-1,3,7-triene is used as an antimicrobial agent for [inhibiting microbial growth] because of its antimicrobial properties, which can be useful in controlling plant diseases.
Used in Insect Repellent Development:
4,8-Dimethylnona-1,3,7-triene is used as an insect repellent for [deterring insects] due to its anti-insect properties, which can help protect plants from insect damage.

InChI:InChI=1/C11H18/c1-5-7-11(4)9-6-8-10(2)3/h5,7-8H,1,6,9H2,2-4H3

Synthetic route

methyl magnesium iodide (917-64-6) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
With diethyl ether erhitzt den erhaltenen Alkohol mit Essigsaeureanhydrid auf 120-130grad;

Methyltriphenylphosphonium bromide (1779-49-3) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
(i) PhLi, Et2O, (ii) /BRN= 1721871/; Multistep reaction;

3,6,6-trimethyl-(4at,8at)-hexahydro-3r,5c-ethano-pyrano[3,4-c]pyran-1,8-dione (5988-79-4, 93354-31-5) → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
copper at 190 - 210℃; for 8h;

methylmagnesium iodide + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) + diluted acid → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
Wasserabspaltung aus dem primaer gebildeten Alkohol;

methyl magnesium (1+); bromide + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) + diluted acid → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
infolge Wasserabspaltung dem primaer gebildeten Alkohol;

pinacolboratamethylenetriphenylphosphonium iodide + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
Stage #1: pinacolboratamethylenetriphenylphosphonium iodide With lithium hexamethyldisilazane In N,N,N,N,N,N-hexamethylphosphoric triamide at 0℃; for 2h; Stage #2: (E/Z)-3,7-dimethyl-2,6-octadienal In N,N,N,N,N,N-hexamethylphosphoric triamide at -78 - 20℃;	99 % Chromat.

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + cyclohex-1-en-1-yl trifluoromethane sulfonate (28075-50-5) → C17H28

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Reagent/catalyst; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	94%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (170011-47-9) → (E)-8-(4,8-dimethylnona-3,7-dien-2-yl)-1,4-dioxaspiro[4.5]dec-7-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	88%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + C13H23F3O4SSi → tert-butyl((3-((E)-4,8-dimethylnona-3,7-dien-2-yl)cyclohex-2-en-1-yl)oxy)dimethylsilane

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	85%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + N-(4-methylphenylsulfonyl)-4-[(trifluoromethanesulfonyl)oxy]-1,2,3,6-tetrahydropyridine (606926-42-5) → (E)-4-(4,8-dimethylnona-3,7-dien-2-yl)-1-tosyl-1,2,3,6-tetrahydropyridine

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	85%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + C9H13F3O5S → (E)-6,8,12-trimethyl-5-methylenetrideca-7,11-dien-1-yl acetate

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	85%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 1-cyclopentenyl triflate (28075-49-2) → (E)-1-(4,8-dimethylnona-3,7-dien-2-yl)cyclopent-1-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	83%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 5,6-dihydro-4-trifluoromethylsulfonyloxy-2H-pyran (188975-30-6) → (E)-4-(4,8-dimethylnona-3,7-dien-2-yl)-3,6-dihydro-2H-pyran

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	81%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 7-oxo-7-(p-tolylamino)hept-1-en-2-yl trifluoromethanesulfonate → (E)-7,9,13-trimethyl-6-methylene-N-(p-tolyl)tetradeca-8,12-dienamide

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	80%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene (77412-96-5) → 4-(tert-butyl)-1-((E)-4,8-dimethylnona-3,7-dien-2-yl)cyclohex-1-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	79%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + PhCH2CH2C(=CH2)OTf → (E)-(4,6,10-trimethyl-3-methyleneundeca-5,9-dien-1-yl)benzene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	79%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + methyl 6-(((trifluoromethyl)sulfonyl)oxy)hept-6-enoate → C19H32O2

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	79%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + C23H24F4O5S → (E)-7,9,13-trimethyl-6-methylenetetradeca-8,12-dien-1-yl 2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanoate

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	74%

3,6-dihydro-2H-thiopyran-4-enol trifluoromethanesulfonate (181180-42-7) + 4,8-dimethyl-1,3,7-nonatriene (51911-82-1) → (E)-4-(4,8-dimethylnona-3,7-dien-2-yl)-3,6-dihydro-2H-thiopyran

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	72%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 4-phenylcyclohex-1-enyl trifluoromethanesulfonate (122948-47-4) → C23H32

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	72%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + ethyl 4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-enecarboxylate (122948-57-6) → ethyl 4-((E)-4,8-dimethylnona-3,7-dien-2-yl)cyclohex-3-ene-1-carboxylate

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	71%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 3,4-dihydro-1-naphthyl triflate (123994-49-0) → 4-((E)-4,8-dimethylnona-3,7-dien-2-yl)-1,2,3,8a-tetrahydronaphthalene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	71%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 1-cyclooctenyl triflate (28075-35-6) → (E)-1-(4,8-dimethylnona-3,7-dien-2-yl)cyclohept-1-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	69%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + hept-1-en-2-yl trifluoromethanesulfonate → (E)-2,6,8-trimethyl-9-methylenetetradeca-2,6-diene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	63%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + cyclohept-1-en-1-yl trifluoromethanesulfonate (28075-51-6) → (E)-1-(4,8-dimethylnona-3,7-dien-2-yl)cyclohept-1-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	62%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 7-hydroxyhept-1-en-2-yl trifluoromethanesulfonate → (E)-6,8,12-trimethyl-5-methylenetrideca-7,11-dien-1-ol

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	62%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 3-hydroxycyclohex-1-en-1-yl trifluoromethanesulfonate (109459-30-5) → 3-((E )-4,8-dimethylnona-3,7-dien-2-yl)cyclohex-2-en-1-ol

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	60%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + (4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-3,4,4a,5,6,7-hexahydronaphthalen-2-yl trifluoromethanesulfonate (1346777-33-0) → (2R,8R,8aS)-6-((E)-4,8-dimethylnona-3,7-dien-2-yl)-8,8a-dimethyl-2-(prop-1-en-2-yl)-1,2,3,7,8,8a-hexahydronaphthalene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	53%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + cyclododec-1-en-1-yl trifluoromethanesulfonate (58999-91-0, 58999-92-1) → 1-(4,8-dimethylnona-3,7-dien-2-yl)cyclododec-1-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	47%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + Acetic acid (8R,9S,10R,13S,14S)-10,13-dimethyl-3-trifluoromethanesulfonyloxy-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (81827-59-0) → (8R,9S,10R,13S,14S)-3-((E)-4,8-dimethylnona-3,7-dien-2-yl)-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylacetate

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	46%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + methyl 2-diazo-3-oxo-3-(pyrrolidin-1-yl)propanoate (135747-07-8) → methyl 2-((E)-2,6-dimethylhepta-1,5-dienyl)-1-(pyrrolidin-1-ylcarbonyl)cyclopropanecarboxylate (1198573-97-5)

Conditions	Yield
With tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh) In 1,2-dichloro-ethane at 25℃; for 16h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	45%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 3-acetoxy-3-(4-methoxyphenyl)prop-1-yne (99520-55-5) → (1E,4Z)-7-(4-methoxyphenyl)-6-methyl-6-(4-methylpent-3-enyl)cyclohepta-1,4-dienyl acetate

Conditions	Yield
With [{(2-biphenyl)-di-tBu-phosphine}Au]SbF6 In 1,2-dichloro-ethane at 25 - 120℃; for 12.5h; Cope rearrangement; stereoselective reaction;	37%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) → 5-allyl-1,5-dimethyl-cyclohexene

Conditions	Yield
With sulfuric acid

Upstream product

• 917-64-6 methyl magnesium iodide 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 689-67-8 pseudo-ionone 
• 5988-79-4 3,6,6-trimethyl-(4at,8at)-hexahydro-3r,5c-ethano-pyrano[3,4-c]pyran-1,8-dione 

Downstream Products

• 1603001-86-0 (E)-N-(4,8-dimethylnona-3,7-dien-2-yl)aniline 
• 1603002-29-4 (Z)-N-(4,8-dimethylnona-3,7-dien-2-yl)aniline 

Relevant academic research and scientific papers

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Pinacolboratamethyl-enetriphenylphosphonium iodide, a new methylene transfer reagent

The title compound is easily prepared and reacts with various aldehydes and ketone. The reagent is compatible with free hydroxy groups. Yields with various aldehydes and ketones are in 50- > 99% range. Both aliphatic, aromatic and unsaturated carbonyls react.