18402-82-9

Usage

Uses

Used in Food and Beverage Industry:
3-Octen-2-one is used as a flavor and fragrance ingredient for its strong, fruity odor, enhancing the aroma and taste of various food and beverage products.
Used in Organic Synthesis:
3-Octen-2-one serves as a key intermediate in organic synthesis, contributing to the production of various chemical compounds and materials.
Used as a Solvent in Chemical Reactions:
In the chemical industry, 3-Octen-2-one is utilized as a solvent to facilitate specific chemical reactions, aiding in the process of synthesis and production of desired compounds.
Used in Wine Aroma:
3-Octen-2-one is used in the wine industry as one of the odor-active components, contributing to the distinctive aroma of several types of wine, thereby enhancing the sensory experience for consumers.

InChI:InChI=1/C8H14O/c1-3-4-5-6-7-8(2)9/h6-7H,3-5H2,1-2H3/b7-6+

Upstream product

• 542-69-8 1-iodo-butane 
• 50285-32-0 1-Methyl-1-methoxyallen 
• 109-72-8 n-butyllithium 
• 1423-60-5 methyl ethynyl ketone 
• 110-62-3 pentanal 
• 67-64-1 acetone 
• 7642-04-8 cis-2-octene 
• 88909-46-0 (E)-4-tert-Butylsulfanyl-2-methoxy-oct-2-ene 
• 64545-10-4 (E)-(hex-1-en-1-yl)dimethyl(phenyl)silane 
• 75-36-5 acetyl chloride 
• 57648-55-2 (E)-oct-3-en-2-ol 
• 82150-00-3 4-hydroxyoctan-2-one 
• 592-41-6 1-hexene 
• 78-94-4 methyl vinyl ketone 

Downstream Products

• 420849-79-2 (2R,3S)-1-(3-butyl-oxiranyl)-ethanone 
• 420849-79-2 (2S,3R)-1-(3-butyl-oxiranyl)-ethanone 
• 57648-55-2 (E)-oct-3-en-2-ol 
• 111-13-7 hexyl-methyl-ketone 
• 1226862-48-1 (S)-4-(5-phenyl-2H-tetrazol-2-yl)octan-2-one 
• 1226862-51-6 (S)-4-(5-(m-tolyl)-2H-tetrazol-2-yl)octan-2-one 
• 1226862-50-5 (S)-4-(5-(p-tolyl)-2H-tetrazol-2-yl)octan-2-one 
• 1226862-52-7 (S)-4-(5-(o-tolyl)-2H-tetrazol-2-yl)octan-2-one 
• 1226862-53-8 (S)-4-[5-(p-bromophenyl)-2H-tetrazol-2-yl]octan-2-one 
• 875431-02-0 (4S,5R)-1-[5-butyl-2-phenyl-1,3,2-dioxaborolan-4-yl]ethanone 
• 1381884-77-0 (4R,5S)-4-butyl-3-(4-chlorobenzoyl)-5-(2,5,5-trimethyl-[1,3]-dioxan-2-yl)oxazolidin-2-one 
• 1449281-65-5 (E)-4-methyl-N-(2-oxooct-3-en-1-yl)-N-tosylbenzenesulfonamide 

Relevant academic research and scientific papers

Low catalyst loading in the cross metathesis of olefins with methyl vinyl ketone

An olefin-metathesis catalyst featuring a 1,3-bis(2,6-diisopropylphenyl)-4, 5-dihydroimidazol-2-ylidene N-heterocyclic carbene and an ester-chelating carbene ligand efficiently promoted the cross metathesis of olefins with 3-buten-2-one in the presence of copper iodide as cocatalyst. At optimized reaction conditions a 10-20 times lower catalyst loading compared to the state of the art could be achieved. Georg Thieme Verlag Stuttgart New York.

A rapid and simple cleanup procedure for metathesis reactions

Figure presented A new method for easy removal of ruthenium from metathesis reactions by using a polar isocyanide is reported. This protocol removed most ruthenium byproducts from a variety of synthetically useful metatheses. Moreover, the isocyanide-promoted carbene insertion results in rapid destruction of carbene reactivity, demonstrated in the commonly used first- and second-generation Grubbs' carbenes.

Biocatalytic Enantioselective Oxidation of Sec-Allylic Alcohols with Flavin-Dependent Oxidases

The oxidation of allylic alcohols is challenging to perform in a chemo- as well as stereo-selective fashion at the expense of molecular oxygen using conventional chemical protocols. Here, we report the identification of a library of flavin-dependent oxidases including variants of the berberine bridge enzyme (BBE) analogue from Arabidopsis thaliana (AtBBE15) and the 5-(hydroxymethyl)furfural oxidase (HMFO) and its variants (V465T, V465S, V465T/W466H and V367R/W466F) for the enantioselective oxidation of sec-allylic alcohols. While primary and benzylic alcohols as well as certain sugars are well known to be transformed by flavin-dependent oxidases, sec-allylic alcohols have not been studied yet except in a single report. The model substrates investigated were oxidized enantioselectively in a kinetic resolution with an E-value of up to >200. For instance HMFO V465S/T oxidized the (S)-enantiomer of (E)-oct-3-en-2-ol (1 a) and (E)-4-phenylbut-3-en-2-ol with E>200 giving the remaining (R)-alcohol with ee>99% at 50% conversion. The enantioselectivity could be decreased if required by medium engineering by the addition of cosolvents (e. g. dimethyl sulfoxide).

Copper(II)-Catalyzed Tandem Decarboxylative Michael/Aldol Reactions Leading to the Formation of Functionalized Cyclohexenones

This work describes the development of a new single-pot copper(II)-catalyzed decarboxylative Michael reaction between β-keto acids and enones, followed by in situ aldolization, which results in highly functionalized chiral and achiral cyclohexenones. The achiral version of this Robinson annulation features a hitherto unprecedented Michael reaction of β-keto acids with sterically hindered β,β′-substituted enones and provides access to all carbon quaternary stereocenter-containing cyclohexenones (11 examples, 43-83% yield). In addition, an asymmetric chiral bis(oxazoline) copper(II)-catalyzed single-pot Robinson annulation has been devised for preparing chiral cyclohexenones, including some products that contain vicinal stereocenters (5 examples, 65-85% yield, 84-94% ee). This latter protocol has been successfully applied to the enantioselective formation of the oxygenated 10-nor-steroid core from readily available starting materials.

Iron-catalyzed aerobic oxidation of allylic alcohols: The issue of C=C bond isomerization

An aerobic oxidation of allylic alcohols using Fe(NO3) 3·9H2O/TEMPO/NaCl as catalysts under atmospheric pressure of oxygen at room temperature was developed. This eco-friendly and mild protocol provides a convenient pathway to the synthesis of stereodefined α,β-unsaturated enals or enones with the retention of the C-C double-bond configuration.

A convenient route to (E)-α,β-unsaturated methyl ketones

Aldehydes are converted into (E)-α,β-unsaturated methyl ketones in good yield and with a high E stereoselectivity using α,α- bis(trimethylsilyl) N-tert-butyl acetimine 3. The reaction was mediated by a catalytic amount of tetrabutylammonium fluoride (TBAF) under mild conditions. The disilylated reagent 3 is easily generated from N-tert-butylacetimine, lithium diisopropylamide (LDA), and chlorotrimethylsilane. The mechanism of the reaction is discussed. Copyright

Na4H3[SiW9Al3(H2O)3O37]·12H2O/H2O: a new system for selective oxidation of alcohols with H2O2 as oxidant

This work describes a catalytic system consisting of both Na4H3[SiW9Al3(H2O)3O37]·12H2O(SiW9Al3) and water as solvents (a?small quantity of organic solvents were used as co-solvent for a few substrates) that can be good for selective oxidation of alcohols to ketones (aldehydes) using 30% H2O2 without any phase-transfer catalyst under mild reaction conditions. The catalyst system allows easy product/catalyst separation. Under the given conditions, the secondary hydroxyl group was highly chemoselectively oxidized to the corresponding ketones in good yields in the presence of primary hydroxyl group within the same molecule, and hydroxides are selectively oxidized even in the presence of alkene. Benzylic alcohols were selectively oxidized to the corresponding benzaldehydes in good yields without over oxidation products in solvent-free conditions. Nitrogen, oxygen, sulfur-based moieties, at least for the cases where these atoms are not susceptible to oxidation, do not interfere with the catalytic alcohol oxidation.

Oxidation of allylic alcohols to α,β-unsaturated carbonyl compounds with aqueous hydrogen peroxide under organic solvent-free conditions

Allylic alcohols are chemoselectively oxidized to α,β- unsaturated carbonyl compounds in high yield with aqueous H2O 2 in the presence of Pt black catalyst under organic solvent-free conditions. The catalyst is easily recyclable and effective for at least 7 cycles. The Royal Society of Chemistry.

Acceptor-free alcohol dehydrogenation by recyclable ruthenium catalyst

An efficient oxidant-free oxidation for a wide range of alcohols was achieved by a recyclable ruthenium catalyst. The catalyst was prepared from readily available reagents by a one-pot synthesis through nanoparticle generation and gelation.

Hydroxyapatite-supported palladium nanoclusters: A highly active heterogeneous catalyst for selective oxidation of alcohols by use of molecular oxygen

Treatment of a stoichiometric hydroxyapatite (HAP), Ca10(PO 4)6(OH)2, with PdCl2(PhCN) 2 gives a new type of palladium-grafted hydroxyapatite. Analysis by means of powder X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), energy-dispersive X-ray (EDX), IR, and Pd K-edge X-ray absorption fine structure (XAFS) proves that a monomeric PdCl2 species is chemisorbed on the HAP surface, which is readily transformed into Pd nanoclusters with a narrow size distribution in the presence of alcohol. Nanoclustered Pd 0 species can effectively promote the alcohol oxidation under an atmospheric O2 pressure, giving a remarkably high turnover number (TON) of up to 236 000 with an excellent turnover frequency (TOF) of approximately 9800 h-1 for a 250-mmol-scale oxidation of 1-phenylethanol under solvent-free conditions. In addition to advantages such as a simple workup procedure and the ability to recycle the catalyst, the present Pd catalyst does not require additives to complete the catalytic cycle. The diameters of the generated Pd nanoclusters can be controlled upon acting on the alcohol substrates used. Oxidation of alcohols is proposed to occur primarily on low-coordination sites within a regular arrangement of the Pd nanocluster by performing calculations on the palladium crystallites.