20125-81-9

Usage

Uses

Used in the Food and Beverage Industry:
(E)-Oct-2-en-4-ol is used as a flavoring agent for its sweet, mushroom-like aroma, enhancing the taste and smell of various products in the food and beverage sector.
Used in the Perfume and Fragrance Industry:
(E)-Oct-2-en-4-ol is utilized as a key ingredient in the production of perfumes and fragrances, where its unique scent contributes to the creation of complex and appealing scents.
Used in Cleaning and Sanitizing Products:
Due to its antimicrobial properties, (E)-Oct-2-en-4-ol is employed in some cleaning and sanitizing products to help eliminate harmful microorganisms and maintain a hygienic environment.
Used as a Precursor in Organic Synthesis:
(E)-Oct-2-en-4-ol also serves as a valuable precursor in the synthesis of other organic compounds, contributing to the development of new materials and products across various industries.
Safety Note:
It is important to handle (E)-Oct-2-en-4-ol with care, as it can cause skin and eye irritation when exposed to high concentrations. Proper safety measures should be taken during its use and storage to minimize potential health risks.

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 123-73-9 crotonaldehyde 
• 110-52-1 1,4-dibromo-butane 
• 109-65-9 1-bromo-butane 
• 123-73-9 trans-Crotonaldehyde 
• 4798-61-2 (Z)-oct-2-en-4-ol 
• 119204-41-0 Trimethyl-[((E)-1-propenyl)-pentyloxy]-silane 
• 55947-16-5 α-chlorocrotonaldehyde 
• 110-62-3 pentanal 
• 52835-06-0 (Z)-hex-1-enyl(trimethyl)silane 
• 93399-87-2 erythro-3,4-epoxy-2-octanol 
• 93399-87-2 threo-3,4-epoxy-2-octanol 
• 41746-22-9 oct-3-yn-2-ol 
• 69668-89-9 (Z)-2-hydroxy-3-octene 

Downstream Products

• 93400-00-1 (2-octen-4-yl) benzyl oxide 
• 1378962-97-0 (E)-2-(4-chlorophenyl)-5-(3-octen-2-yl)-1,3,4-oxadiazole 
• 1378962-69-6 (E)-2-(3-octen-2-yl)-4-phenyloxazole 
• 570368-42-2 (1S,2Z)-1-butyl-2-butenyl 2,3,4,5,6-pentafluorobenzoate 
• 570368-33-1 1-isobutyl-4-[(1R,2E)-1-methyl-2-heptenyl]benzene 

Relevant academic research and scientific papers

PERFUME SYSTEM FOR PERFUMED CONSUMER PRODUCT

The present invention relates to a perfume system comprising a core-shell microcapsule A, optionally, a core-shell microcapsule B, and optionally, a free perfume oil, wherein the core of the core-shell microcapsule A and/or the free perfume oil comprises a 2-oxoacetate derivative of formula (I) as well as a perfumed consumer product comprising the same and methods and uses of the same for enhancing, conferring, increasing and/or modifying the fragrance properties and/or the fragrance intensity of perfumed consumer products.

Chirality Transfer in Gold(I)-Catalysed Direct Allylic Etherifications of Unactivated Alcohols: Experimental and Computational Study

Gold(I)-catalysed direct allylic etherifications have been successfully carried out with chirality transfer to yield enantioenriched, γ-substituted secondary allylic ethers. Our investigations include a full substrate-scope screen to ascertain substituent effects on the regioselectivity, stereoselectivity and efficiency of chirality transfer, as well as control experiments to elucidate the mechanistic subtleties of the chirality-transfer process. Crucially, addition of molecular sieves was found to be necessary to ensure efficient and general chirality transfer. Computational studies suggest that the efficiency of chirality transfer is linked to the aggregation of the alcohol nucleophile around the reactive π-bound Au-allylic ether complex. With a single alcohol nucleophile, a high degree of chirality transfer is predicted. However, if three alcohols are present, alternative proton transfer chain mechanisms that Erode the efficiency of chirality transfer become competitive.

Suzuki-Miyaura cross-couplings of secondary allylic boronic esters

Palladium-catalyzed cross-coupling reactions of secondary allylic boronic esters with iodoarenes were demonstrated under the conditions previously described for the coupling of benzylic substrates. The regioselectivity of the process was largely dictated by the pattern of olefin substitution. The Royal Society of Chemistry 2012.

Pd(II)-catalyzed aliphatic Claisen rearrangements of acyclic allyl vinyl ethers

Palladium (II)-catalyzed [3,3] sigmatropic rearrangement of acyclic allyl vinyl ethers delivers 2,3-anti disubstituted pentenal Claisen adducts with high diastereoselectivity. Reaction conditions for circumventing allyl vinyl ether cleavage that had previ

Synthesis of vinyl 1,2-diketones

A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by 1O2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones.

Acid-catalyzed rearrangement of α-hydroxytrialkylsilanes

Cationic rearrangement of several α-hydroxysilanes is described. Treatment of both (1R,1′R,2′S)-α-hydroxycyclopropylsilane syn-9 and (1S,1′R,2′S)-anti-9 under aqueous H2SO4 underwent rearrangement via a common α-silyl cation intermediate A to give a mixture of the ring-opened (R)-vinylsilane 13, the tandem [1,2]-CC bond migration product (1R,2S,1′R)-14, and its 1′S isomer 15. On the other hand, the acidic treatment of (R,E)-α-hydroxyalkenylsilane 8 or (R,Z)-8 was each accompanied with partial racemization to give an enantiomeric isomer of allylic alcohol 23 via a preferential syn-facial SN2′ reaction, respectively. Both α-hydroxyalkynylsilane 6 and α-hydroxyalkylsilane 12 were inert to the acidic conditions; however, treatment of (R)-α-mesyloxyalkynylsilane 26 under aqueous H2SO4 gave a mixture of the optically active rearranged allene 27, α,β-unsaturated ketone 28, and (S)-α-hydroxyalkynylsilane 6 with partial racemization. Comparisons of the reactivities of these α-hydroxysilanes under acidic conditions are also disclosed.

Stereoselective reactions of acyclic allylic phosphates with organocopper reagents

A series of acyclic allylic alcohols of general structure R1CH=CHCH(OH)R2 were resolved by Sharpless kinetic resolution. The hydroxyl groups of these enantiomerically enriched alcohols were derivatized to diethyl phosphates, and the derivatives were reacted with organocopper reagents. Cleanest substitution reactions were observed with reagents R32CuCNLi2. With R1 = Me and R3 = n-Bu, the size of R2 affected both the regioselectivity and stereoselectivity of the displacement. Larger R2 groups gave higher regio- and stereoselectivities: with R2 = 3-pentyl, >98% SN2′ regioselectivity and > 98% anti stereoselectivity were observed. Bn2CuCNLi2 gave stereoselectivities comparable to those observed with n-Bu2CuCNLi2 but t-Bu2CuCNLi2 exhibited much lower diastereofacial preference.

The regioselective 1,4-addition reaction of alkenylboronic acids to α,β,α′,β′-unsaturated ketones

The effect of substituents on the double bond of α,β-unsaturated ketones for the 1,4-addition reaction rate of alkenylboronic acids induced by cyanuric fluoride was studied in detail. When the steric hindrance around the β-carbon of the unsaturated ketones increased, the 1,4-addition reaction rate significantly decreased. An alkyl substituent on the α-carbon was also found to significantly affect the 1,4-addition reaction. From these results, unsymmetric α,β,α′,β′unsaturated ketones (10a-f) were designed for the regioselective 1,4-addition reaction with alkenylboronic acids (4a-j). Since they have substituents to disturb the 1,4-addition reaction on only one double bond, the alkenylboronic acids reacted with them from only one side to selectively provide γ,δ,α′,β′-unsaturated ketones (11a-q). Further transformations of the resulting γ,δ,α′,β′-unsaturated ketones were also performed.

A Highly Regioselective Reaction of Allylic Acetates with Silylated Carbon Nucleophiles Directed by a Sulfenyl Group. Scope, Limitation, and Mechanistic Aspects

α-(Sulfenylmethyl)allyl acetates reacted with silylated carbon nucleophiles in the presence of a catalytic amount of TMSOTf to give products substituted at the α-position of the sulfenylmethyl group in moderate to good yields with high regioselectivity.The theoretical calculation on an intermediate cationic species indicated that an episulfonium ion was a stable form; the observed regioselectivity was rationalized qualitatively on the basis of the coefficients of LUMO of the cation.Some transformations of the products were also demonstrated.

On the Mechanism of Organoaluminum-Promoted Claisen Rearrangement of Allylic Vinyl Ethers

The organoaluminum-promoted Claisen rearrangement of allylic vinyl ethers has been mechanistically studied by two sets of experiments and the observed Z and E selectivity is best accounted for by two possible chair-like structures with R substituents axial and equatorial, respectively.