67548-26-9

Usage

Uses

Used in Perfumery and Flavor Industry:
(E)-2-METHYL-HEPTA-2,6-DIEN-1-OL is used as a key ingredient in the perfumery and flavor industry for its pleasant, floral scent. It contributes to the creation of various fragrances and flavors, enhancing the sensory experience of consumers.
Used in Organic Synthesis:
(E)-2-METHYL-HEPTA-2,6-DIEN-1-OL is used as a building block in the synthesis of other organic compounds. Its unique structure allows for the formation of a wide range of molecules, making it a valuable asset in the field of organic chemistry.
Used as a Chemical Intermediate:
In addition to its direct applications, (E)-2-METHYL-HEPTA-2,6-DIEN-1-OL serves as an intermediate in various chemical reactions. This role is essential for the production of a multitude of chemical products, further highlighting its importance in the chemical industry.
Safety Precautions:
It is important to handle (E)-2-METHYL-HEPTA-2,6-DIEN-1-OL with care, as it can be harmful if inhaled or comes into contact with the skin. Proper storage and usage in a well-ventilated area are necessary to minimize risks. Additionally, (E)-2-METHYL-HEPTA-2,6-DIEN-1-OL should be kept away from sources of ignition and incompatible materials to prevent accidents or unwanted chemical reactions.

Upstream product

• 2100-17-6 4-pentenal 
• 1838-94-4 isoprene epoxide 
• 1730-25-2 allylmagnesium bromide 
• 104643-23-4 (E)-2-methyl-hepta-2,6-dienoic acid 
• 187749-59-3 (R)-2-Methyl-2-pent-4-enyl-oxirane 
• 18759-99-4 allyl(diethyl)borane 
• 2622-05-1 allylmagnesium bromide 
• 78-79-5 isoprene 
• 132925-37-2 (E)-7-<(Bromomethyl)dimethylsilyloxy>-6-methylhepta-1,5-diene 
• 129694-16-2 ethyl (E)-2-methylhepta-2,6-dienoate 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 107319-99-3 (4R,5R)-4-methyl-5-<(3,5-dinitrobenzoyloxy)methyl>-5-hexanolide 
• 109922-52-3 3,5-Dinitro-benzoic acid (2R,3R)-2-hydroxy-2,3-dimethyl-hept-6-enyl ester 
• 64309-03-1 6-isopropenyl-3-methyl-9-decenyl acetate 

Relevant academic research and scientific papers

Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction

Bicyclic ether scaffolds are found in a variety of natural products and are of interest in probe and drug discovery. A palladium-catalyzed cascade reaction has been developed to provide efficient access to these scaffolds from readily available linear diene-diol substrates. A Pd redox-relay process is used strategically to transmit reactivity between an initial oxypalladative cyclization and a subsequent π-allyl-Pd cyclization at remote sites. The reaction affords a variety of bicyclic ether scaffolds with complete diastereoselectivity for cis-ring fusion.

B(C6F5)3: A New Class of Strong and Bulky Lewis Acid for Exo-Selective Intermolecular Diels-Alder Reactions of Unreactive Acyclic Dienes with α,β-Enals

Lewis acid B(C6F5)3 catalyzed the Diels-Alder reactions of multisubstituted open-chain dienes and α,β-enals to afford the desired products with high exo-selectivities are reported. The substituent effect of the dienes and dienophiles on the products stereoselectivity was thoroughly investigated, and it was found that most of the desired exo-Diels-Alder products could be obtained in good yields and with high exo-stereoselectivities.

Construction of enantioenriched cyclic compounds by asymmetric allylic alkylation and ring-closing metathesis

A new approach to highly enantioenriched cyclic compounds (up to 98a€‰% ee) has been developed by using ω-ethylenic allylic substrates in a one-pot asymmetric allylic alkylation and ring-closing metathesis sequence. The starting compounds are synthetic equivalents of cyclic allylic substrates. The method is exemplified with both Cu and Ir catalysts, and chiral phosphoramidite ligands. A new approach to highly enantioenriched cyclic compounds (up to 98a€‰% ee) has been developed by using ω-ethylenic allylic substrates in a one-pot asymmetric allylic alkylation and ring-closing metathesis sequence. The starting compounds are synthetic equivalents of cyclic allylic substrates. The method is exemplified with both Cu and Ir catalysts, and chiral phosphoramidite ligands. Copyright

Computationally guided organometallic chemistry: Preparation of the heptacyclic pyrazine core of ritterazine N

Diels-Alder cycloaddition of 10 followed by Wittig homologation and intramolecular diene cyclozirconation of the resulting triene under equilibrating conditions led to the tricyclic 6-6-5 ketone 5 with high diastereocontrol. The derived α-azido ketone 16

Syntheses with Organoboranes. XI. Allylboration of Vinylic Epoxides with Allylic Dialkylboranes

equation presented Allylboration of representative vinylic epoxides with allyldiethylborane (1) and (2-cyclohexenyl)dicyclohexylborane (2) affords the corresponding 1,2- and 1,4-addition products. cis-1,2-Addition is favored in the reaction of 1 with 3,4-

Chemoenzymatic deracemization of (±)-2,2-disubstituted oxiranes

The preparation of vicinal diols in up to 98% e.e. and 98% yield from the corresponding (±)-2,2-disubstituted epoxides was achieved via an enantioconvergent two-step hydrolysis: Thus, enantioselective enzymatic hydrolysis of the (S)-epoxide proceeded with retention of configuration furnishing the corresponding (S)-diol. In a subsequent step, the remaining (R)-oxirane was hydrolyzed during workup under acid catalysis with complete inversion of configuration yielding the (5)-diol. A detailed study of the latter reaction revealed that the experimental conditions have to be carefully chosen with respect to (i) nature of the acid, (ii) the solvent, and (iii) its water content to avoid racemization.

Total Synthesis of Optically Active Integerrimine, a Twelve-membered Dilactonic Pyrrolizidine Alkaloid of Retronecine Type

A total synthesis of the natural enantiomer of integerrimine (1), a twelve-membered dilactonic pyrrolizidine alkaloid of retronecine type has been achieved through the enantioselective synthesis and regioselective coupling of (+)-retronecine (4) and (+)-integerrinecic acid (methylthio)methyl ether (6).

Reductive Radical Cyclisations of Bromo Acetals and (Bromomethyl)silyl Ethers of Terpenoid Alcohols

The tin hydride promoted and the reductive vitamin B12 catalysed radical cyclisation of mixed 2-bromoacetaldehyde acetals and of (2-bromomethyl)dimethylsilyl ethers of allylic terpenoid alcohols has been investigated: 3-oxadeca-5,9-dien-1-yl radicals undergo 5-'exo' cyclisation to oxolanes (Scheme 4), 3-oxa-2-siladeca-5,9-dien-1-yl radicals sequential 6-'endo' --> 5-'exo' tandem cyclisation to cis-3-oxa-4-silabicyclononanes (Scheme 5), and 3-oxa-2-silatetradeca-5,9,13-trien-1-yl radicals sequential 6-'endo' --> 6-'endo' --> 5-'exo' triple cyclisation to trans-transoid-trans-12-oxa-11-silatricyclo2.6>tridecanes (Scheme 6).

A Short and Formal Synthesis of California Red Scale Pheromone

A short and efficient synthesis of 3-isopropenyl-hept-6-en-1-al, an intermediate of California red scale pheromone, has been described.Claisen orthoester rearrangement has been employed as a key step in the scheme.

TOTAL SYNTHESIS OF OPTICALLY ACTIVE INTEGERRIMINE, A TWELVE-MEMBERED DILACTONIC PYRROLIZIDINE ALKALOID OF RETRONECINE TYPE. I. ENANTIOSELECTIVE SYNTHESIS OF THE PROTECTED (+)-INTEGERRINECIC ACID

For the total synthesis of optically active integerrimine, the twelve-membered dilactonic pyrrolizidine alkaloid, the necic acid component (+)-integerrinenic acid has been enantioselectively synthesized in the protected form.