41610-76-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 4657, 1993 DOI: 10.1016/S0040-4039(00)60649-4

InChI:InChI=1/C12H20O3/c1-6-12(5,14-9(2)13)8-7-10-11(3,4)15-10/h6,10H,1,7-8H2,2-5H3

Upstream product

• 115-95-7 linalool acetate 

Downstream Products

• 29210-77-3 2,6-dimethyloct-7-ene-2,6-diol 
• 76338-31-3 6-acetoxy-2-hydroxy-2,6-dimethyl-3-phenylseleno-octa-7-ene 
• 73815-21-1 3,7-dimethyloct-1-ene-3,6,7-triol 
• 68754-14-3 1-acetoxy-trans-p-mentha-2,8-diene 
• 76338-36-8 1α-acetoxy-trans-p-menth-2-en-8-ol 
• 76338-37-9 1,8-diacetoxy-trans-p-menth-2-ene 
• 76338-32-4 Acetic acid (1R,2S,4S)-4-isopropenyl-1-methyl-2-phenylselanyl-cyclohexyl ester 
• 76338-33-5 1α-acetoxy-2α-phenylseleno-trans-p-menthan-8-ol 
• 76358-34-4 Trifluoro-acetic acid 1-((1R,3R,4S)-4-acetoxy-4-methyl-3-phenylselanyl-cyclohexyl)-1-methyl-ethyl ester 
• 74756-09-5 1α-hydroxy-2α-phenylseleno-trans-p-menth-8-ene 
• 66521-02-6 (E)-10-hydroxy-4,10-dimethyl-dodeca-4,11-dien-2-one 
• 70130-98-2 4-Acetoxy-4-methyl-5-hexenyl-p-toluolsulfonat 
• 64708-28-7 2,2,5-trimethyl-4-cyclohepten-1-ol 

Relevant academic research and scientific papers

ANTIFUNGAL COMPOUNDS DERIVED FROM LAVENDER OIL

Epoxides and hydroperoxide compounds having antifungal activities derived from the oxidation linalyl acetate, a major component of lavender oil, are disclosed. Also, disclosed are pharmaceutical composition and methods of treating and protecting a subject from fungal infection.

Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants

Dirhodium(II) complexes and iodine(III) oxidants have found useful applications in synthetic nitrene chemistry. In this study, the combination of the dirhodium(II) complex Rh2(tpa)4 (tpa = triphenylacetate) with the iodine(III) oxidant PhI(OPiv)2 is shown to promote the epoxidation of alkenes in the presence of 2 equivalents of water. The reaction can be applied to diversely substituted alkenes and the corresponding epoxides are isolated with yields of up to 90 %. A possible mechanism involves the dirhodium(II) complex as a Lewis acid species that would tune the oxidizing character of the iodine(III) reagent.

Catalytic homogeneous oxidation of monoterpenes and cyclooctene with hydrogen peroxide in the presence of sandwich-type tungstophosphates [M4(H2O)2(PW9O34)2]n?, M = CoII, MnII and FeIII

Catalytic efficiency of tetrabutylammonium salts of sandwich tungstophosphates B‐α‐[M4(H2O)2(PW9O34)2]n?, M = CoII, MnII, FeIII, was studied in the oxidation of (R)-(+)-limonene, geraniol, linalool, linalyl acetate, carveol, and cis-cyclooctene with hydrogen peroxide, in acetonitrile. Oxidation of (R)-(+)-limonene gave limonene-1,2-diol as main product. Epoxidation of linalool takes place preferentially at the more substituted 6,7-double bond, the corresponding 6,7-epoxide reacting further, yielding furano- and pyrano-oxides, via intramolecular cyclization. Oxidation of linalyl acetate occurred preferentially at the more substituted 6,7-double bond for Mn4(PW9)2, affording 6,7-epoxide at 82% selectivity. Linalyl acetate 1,2-epoxide was the major product with 51% and 77% selectivity for Co4(PW9)2 and Fe4(PW9)2, respectively. Oxidation of carveol occurred with very good conversions in the presence of Mn4(PW9)2, Co4(PW9)2 and Fe4(PW9)2, yielding carvone and carveol 1,2-epoxide in similar amounts. Oxidation of cis-cyclooctene gave only the epoxide, while oxidation of geraniol at room temperature afforded 2,3-epoxygeraniol as the major product.

A versatile method of epoxide formation with the support of peroxy ionic liquids

The application of the peroxy ionic liquid, 1-butyl-3-methylimidazolium peroxymonosulphate, as an oxidation agent and a solvent for the synthesis of epoxides was described. The 2.5-molar excess of the peroxy ionic liquid to olefin was applied. The reaction system consisted of 1,1,1-trifluoroacetone as an oxirane precursor, which was used with the molar ratio of 1:3 relative to olefin and water solution of NaHCO3. Under these conditions the epoxidation of 4-bromocinnamic acid led to the epoxide formation at the ambient temperature in 30 minutes. Dioxiranes, generated from the peroxy ionic liquid and 1,1,1-trifluoroacetone, demonstrated encouraging potential for the epoxidation of a variety of other olefins: styrene, limonene, stilbene, linalyl acetate and a complex steroid molecule with high yields of final epoxides from 65-98%.

Catalytic performance of a boron peroxotungstate complex under homogeneous and heterogeneous conditions

The preparation and characterization (FT-IR, FT-Raman, 11B MAS NMR, diffuse reflectance, elemental analysis) of a novel boron peroxotungstate (BTBA)4H[BW4O24] (BTBA = benzyltributylammonium) is reported, along with its use in the homogeneous oxidation of cis-cyclooctene, geraniol, linalool and (-)-carveol with H 2O2 as oxidant and acetonitrile as solvent. High catalytic activity was registered for all the substrates studied under homogeneous conditions, namely 99% of conversion of geraniol after 2 h, 93% for linalool after 5 h, 74% for cis-cyclooctene after 6 h, and 100% for (-)-carveol after 2 h of reaction. Some oxidation studies were carried out with the Venturello complex, [PW4O24]3-, in the same conditions. Furthermore, the boron peroxotungstate (BW4) was immobilized using two different strategies: (a) BW4 anchored into a functionalized silica (aptesSiO2) giving BW4@aptesSiO2 and (b) BW4 encapsulated on a metal organic framework, commonly referred as MIL-101, giving BW4@MIL-101. The catalytic activity of both heterogeneous materials was investigated for geraniol oxidation and the results were compared with those obtained with BW4 under homogeneous conditions. The encapsulated boron peroxotungstate (BW4@MIL-101) gave rise to the best results, reaching complete conversion of geraniol after 3 h of reaction and 78% selectivity for 2,3-epoxygeraniol. Additionally, this heterogeneous catalyst could be reused without appreciable loss of catalytic activity, affording similar 2,3-epoxygeraniol selectivity. The heterogeneous catalysts' stability was also investigated after the oxidation reactions by different characterization techniques.

Rhodium acetate-catalyzed aerobic Mukaiyama epoxidation of alkenes

Mukaiyama epoxidation of alkenes under oxygen catalyzed by rhodium acetate with isobutyraldehyde as the reducing agent is as or more effective than previously reported procedures. A variety of alkenes, including terpenes and cholesterol derivatives, were oxidized. And high regioselectivity for monoepoxidation was observed with neryl, geranyl, and linalyl acetates.

Selective epoxidation of monoterpenes with methyltrioxorhenium and H2O2

In the presence of pyridine as a co-catalyst, CH3ReO3 catalyses the epoxidation of terpenes such as α-pinene with H2O2 with minimal rearrangement of the epoxide. Pyridine is also critical to suppress isomerisation of the olefin substrate (in case of nerol, geraniol). The reaction can be directed towards selective single or double epoxidation, or in one step towards the rearranged product (e.g. from linalool to the ring- closure product linalool oxide.

(S)-3,7-Dimethyl-5-octene-1,7-diol and Related Oxygenated Monoterpenoids from Petals of Rosa damascena Mill

The methanolic extract obtained from rose flowers was subjected to XAD-2 adsorption chromatography. Prefractionation of the methanolic eluate using multilayer coil countercurrent chromatography (MLCCC) yielded five subfractions. From the least polar subfraction V, a major amount of the key odorants of rose oil, that is, isomeric rose oxides 1a/b, was liberated upon heat treatment at pH 2.5. Further Chromatographic workup of fraction V led, for the first time, to the identification of the genuine rose oxide precursor (S)-3,7-dimethyl-5-octene-1,7-diol (2). In addition to diol 2, the following monoterpene diols have been identified: 3,7-dimethyl-7-octene-1,6-diol (3), 2,6-dimethyl-1,7-octadiene-3,6-diol (4), (2E,5E)-3,7-dimethyl-2,5-octadiene-1,7-diol (5), (2E)-3,7-dimethyl-2,7-octadiene-1,6-diol (6), (2Z,5E)-3,7-dimethyl-2,5-octadiene-1,7-diol (7), (2Z)-3,7-dimethyl-2,7-octadiene-1,6-diol (8), (Z)-2,6-dimethyl-2-octene-1,8-diol (9), (E)-2,6-dimethyl-2-octene-1,8-diol (10), (Z)-2,6-dimethyl-2,7-octadiene-1,6-diol (11), (E)-2,6-dimethyl-2,7-octadiene-1,6-diol (12), (2E,6E)-2,6-dimethyl-2,6-octadiene-1,8-diol (13), (2E,6Z)-2,6-dimethyl-2,6-octadiene-1,8-diol (14), 2,6-dimethyloctane-1,8-diol (15), 2,6-dimethyl-7-octene-1,6-diol (16), (E)-3,7-dimethyl-2-octene-1,8-diol (17), (Z)-3,7-dimethyl-2-octene-1,8-diol (18), 3,7-dimethyloctane-1,7-diol (19), 2,6-dimethyl-7-octene-2,6-diol (20), 3,7-dimethyl-6-octene-1,3-diol (21) and (2E)-3,7-dimethyl-2,6-octadiene-1,4-diol (22).

Cobalt(II)-Catalyzed Reaction of Enolizable Aldehydes with Alkenes in the Presence of Dioxygen: The Role of Acyl Radical

Complex cobalt(II) (1) catalyzes the reaction of enolizable aliphatic aldehydes and dioxygen with an electron-deficient alkene to afford the adducts 4 and 5, whereas the reaction with unactivated alkenes leads to the corresponding epoxides 6.These reactions are proposed to proceed via a common pathway involving acyl radicals.