1669-44-9

Usage

Uses

Used in Flavor and Fragrance Industry:
3-Octen-2-one is used as a flavoring agent for its earthy, oily, and mushroom nuances, adding depth and complexity to various food products. It is commonly found in roasted filberts, asparagus, baked potato, fish, cooked chicken and beef, white wine, peanuts, pecan, oats, soybean, mushroom, trassi, fenugreek, coriander seed, rice bran, cooked scented rice, and corn tortillas.
Used in Perfumery:
3-Octen-2-one is used as a fragrance ingredient for its fruity, lemon odor, contributing to the creation of various scent profiles in perfumes and other fragranced products.
Used in Chemical Synthesis:
3-Octen-2-one can be used as a building block or intermediate in the synthesis of other organic compounds, taking advantage of its reactive ketone and alkene functional groups.

Preparation

By bubbling air in a solution of an organoborane derivative of 1-butene and 1-butyn-2-one in tetrahydrofuran.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 710, 1978 DOI: 10.1021/jo00398a042Synthetic Communications, 19, p. 501, 1989 DOI: 10.1080/00397918908050692

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

Upstream product

• 592-41-6 1-hexene 
• 64-19-7 acetic acid 
• 407-25-0 trifluoroacetic anhydride 
• 1119-58-0 oct-3-yn-2-one 
• 75-36-5 acetyl chloride 
• 110-62-3 pentanal 
• 67-64-1 acetone 
• 76649-14-4 oct-3-en-2-ol 
• 111-66-0 oct-1-ene 
• 13389-42-9 trans-2-Octene 
• 17257-80-6 Z-3,4-epoxy-2-octanone 
• 420849-79-2 trans-3,4-epoxy-2-octanone 
• 108-24-7 acetic anhydride 
• 83810-21-3 acide acetylsulfoacetique 

Downstream Products

• 111-13-7 hexyl-methyl-ketone 
• 124492-23-5 (Z)-4-(4-Acetyl-phenyl)-oct-4-en-2-one 
• 124492-29-1 (E)-4-(4-Acetyl-phenyl)-oct-3-en-2-one 
• 35583-33-6 4-phenyl-2-octanone 
• 1202448-11-0 (1S,6R,E)-tert-butyl 6-butyl-1-fluoro-4-oxo-2-styrylcyclohex-2-enecarboxylate 
• 1202448-37-0 C₂₃H₃₁FO₄ 
• 1224975-71-6 4-(p-fluorophenylthio)octan-2-one 
• 1224975-69-2 4-(p-chlorophenylthio)octan-2-one 
• 1224975-67-0 4-(p-tolylthio)octan-2-one 
• 116671-44-4 4-(phenylthio)octan-2-one 
• 934559-80-5 (-)-(4R)-4-phenyloctan-2-one 
• 1266384-91-1 C₁₅H₂₃NO₂S 
• 1255574-23-2 rac-4-(4-methylphenyl)octan-2-one 
• 4128-31-8 rac-octan-2-ol 

Relevant academic research and scientific papers

Tetrabutylammonium peroxydisulfate in organic synthesis; II. A mild method for cleaving tosylhydrazones with tetrabutylammonium peroxydisulfate

Tosylhydrazones are oxidized with tetrabutylammonium peroxydisulfate in 1,2-dichloroethane to afford the corresponding ketones in excellent yields under neutral conditions.

Mild Chemoenzymatic Oxidation of Allylic sec-Alcohols. Application to Biocatalytic Stereoselective Redox Isomerizations

The design of catalytic oxidative methodologies in aqueous medium under mild reaction conditions and using molecular oxygen as final electron acceptor represents a suitable alternative to the traditional oxidative transformations. These methods are especially relevant if other functionalities that can be oxidized are present within the same molecule, as in the case of allylic alcohols. Herein we apply a simple chemoenzymatic system composed of the laccase from Trametes versicolor and 2,2,6,6-tetramethylpiperidinyloxy radical (TEMPO) to oxidize a series of racemic allylic sec-alcohols into the corresponding α,β-unsaturated ketones. Afterward, these compounds react with different commercially available ene-reductases to afford the corresponding saturated ketones. Remarkably, in the case of trisubstituted alkenes, the bioreduction reaction occurred with high stereoselectivity. Overall, a bienzymatic one-pot two-step sequential strategy has been described with respect to the synthesis of saturated ketones starting from racemic allylic alcohols, thus resembling the metal-catalyzed redox isomerizations of these derivatives that have been previously reported in the literature.

Highly practical and efficient preparation of aldehydes and ketones from aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst

Herein, we divulge an efficient protocol for aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst, (NH4)5[IMo6O24]. The catalyst system is compatible with a wide range of groups and exhibits high selectivity, and shows excellent stability and reusability, thus serving as a potentially greener alternative to the classical transformations.

Cooperative Electrocatalytic and Chemoselective Alcohol Oxidation by Shvo's Catalyst

A new electrocatalytic conversion of alcohols to ketones and aldehydes was developed based on an electrochemical study of Shvo's complex. The oxidation of secondary alcohols was efficiently performed under mild conditions using a catalytic amount of Shvo's catalyst, in combination with a sub-stoichiometric amount of 2,6-dimethoxy-1,4-benzoquinone in N,N-dimethylformamide at 80 °C. The hydroquinone thus formed is continuously reoxidized with the aid of an electrochemical device. Excellent yields for different ketones, aromatic as well as aliphatic and α,β-unsaturated ketones, are obtained. In addition, chemoselectivity towards oxidation of the secondary alcohol is achieved when converting vicinal diols such as 1,2-octanediol and 1,2-decanediol. (Figure presented.).

Characterization of the monolignol oxidoreductase AtBBE-like protein 15 L182V for biocatalytic applications

Monolignol oxidoreductases from the berberine bridge enzyme-like (BBE-like) protein family (pfam 08031) catalyze the oxidation of monolignols to the corresponding aldehydes. In this report, we explore the potential of a monolignol oxidoreductase from Arabidopsis thaliana (AtBBE-like protein 15) as biocatalyst for oxidative reactions. For this study we employed a variant with enhanced reactivity towards oxygen, which was obtained by a single amino acid exchange (L182V). The pH and temperature optima of the purified AtBBE-like protein 15 L182V were determined as well as the tolerance toward organic co-solvents; furthermore the substrate scope was characterized. The enzyme has a temperature optimum of 50 °C and retains more than 50% activity between pH 5 and pH 10 within 5 min. The enzyme shows increased activity in the presence of various co-solvents (10–50% v/v), including acetonitrile, 2-propanol, 1,4-dioxane, and dimethyl sulfoxide. Primary benzylic and primary or secondary allylic alcohols were accepted as substrates. The enantioselectivity E in the oxidation of secondary alcohols was good to excellent (E>34 to?>200).

Crystal Structure and Catalytic Behavior in Olefin Epoxidation of a One-Dimensional Tungsten Oxide/Bipyridine Hybrid

The tungsten oxide/2,2′-bipyridine hybrid material [WO3(2,2′-bpy)]·nH2O (n = 1-2) (1) has been prepared in near quantitative yield by the reaction of H2WO4, 2,2′-bpy, and H2O in the mole ratio of ca. 1:2:700 at 160°C for 98 h in a rotating Teflon-lined digestion bomb. The solid-state structure of 1 was solved and refined through Rietveld analysis of high-resolution synchrotron X-ray diffraction data collected for the microcrystalline powder. The material, crystallizing in the orthorhombic space group Iba2, is composed of a one-dimensional organic-inorganic hybrid polymer, ∞1[WO3(2,2′-bpy)], topologically identical to that found in the previously reported anhydrous phases [MO3(2,2′-bpy)] (M = Mo, W). While in the latter the N,N′-chelated 2,2′-bpy ligands of adjacent corner-shared {MO4N2} octahedra are positioned on the same side of the 1D chain, in 1 the 2,2′-bpy ligands alternate above and below the chain. The catalytic behavior of compound 1 for the epoxidation of cis-cyclooctene was compared with that for several other tungsten- or molybdenum-based (pre)catalysts, including the hybrid polymer [MoO3(2,2′-bpy)]. While the latter exhibits superior performance when tert-butyl hydroperoxide (TBHP) is used as the oxidant, compound 1 is superior when aqueous hydrogen peroxide is used, allowing near-quantitative conversion of the olefin to the epoxide. With H2O2, compounds 1 and [MoO3(2,2′-bpy)] act as sources of soluble active species, namely, the oxodiperoxo complex [MO(O2)2(2,2′-bpy)], which is formed in situ. Compounds 1 and [WO(O2)2(2,2′-bpy)] (2) were further tested in the epoxidation of cyclododecene, trans-2-octene, 1-octene, (R)-limonene, and styrene. The structure of 2 was determined by single-crystal X-ray diffraction and found to be isotypical with the molybdenum analogue.

Chemoselective hydrogen peroxide oxidation of allylic and benzylic alcohols under mild reaction conditions catalyzed by simple iron-picolinate complexes

Chemoselective oxidation of allylic alcohols to α,β-unsaturated carbonyl compounds proceeded efficiently using hydrogen peroxide with iron-picolinate catalysts. The in situ generated [Fe(Me-Pic)3] (Me-Pic = 6-methylpicolinate) catalyzed oxidation of the alcohol moiety of primary allylic alcohols while the [Fe(Pic)3] (Pic = picolinate) and [Fe(Me-Pic)2(Pic)] did not show sufficient catalytic activity. the Partner Organisations 2014.

Chemoselective hydrogen peroxide oxidation of allylic and benzylic alcohols under mild reaction conditions catalyzed by simple iron-picolinate complexes

Chemoselective oxidation of allylic alcohols to α,β-unsaturated carbonyl compounds proceeded efficiently using hydrogen peroxide with iron-picolinate catalysts. The in situ generated [Fe(Me-Pic)3] (Me-Pic = 6-methylpicolinate) catalyzed oxidation of the alcohol moiety of primary allylic alcohols while the [Fe(Pic)3] (Pic = picolinate) and [Fe(Me-Pic)2(Pic)] did not show sufficient catalytic activity. This journal is

Wacker-type oxidation and dehydrogenation of terminal olefins using molecular oxygen as the sole oxidant without adding ligand

An efficient and economical palladium-catalyzed oxidation system has been identified. The oxidation system, characterized by not adding ligand and using molecular oxygen as the sole oxidant, can realize the Tsuji-Wacker oxidation of terminal olefins and especially styrenes to methyl ketones; in addition, this system can achieve tandem Wacker oxidation-dehydrogenation of terminal olefins to α,β-unsaturated ketones.

Gold nanoparticle-catalyzed environmentally benign deoxygenation of epoxides to alkenes

We have developed a highly efficient and green catalytic deoxygenation of epoxides to alkenes using gold nanoparticles (NPs) supported on hydrotalcite [HT: Mg6Al2CO3(OH)16] (Au/HT) with alcohols, CO/H2O or H2 as the reducing reagent. Various epoxides were selectively converted to the corresponding alkenes. Among the novel metal NPs on HT, Au/HT was found to exhibit outstanding catalytic activity for the deoxygenation reaction. Moreover, Au/HT can be separated from the reaction mixture and reused with retention of its catalytic activity and selectivity. The high catalytic performance of Au/HT was attributed to the selective formation of Au-hydride species by the cooperative effect between Au NPs and HT.