15932-80-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Isopropylidene-5-methylcyclohexanone is used as an intermediate in the synthesis of Δ6a,10a-Tetrahydrocannabinol (T298635), a synthetic cannabinoid with psychoactive properties. Its role in the pharmaceutical industry is crucial for the development of new drugs and therapies that target specific medical conditions.
Used in Chemical Synthesis:
In the chemical industry, 2-Isopropylidene-5-methylcyclohexanone serves as a key intermediate in the synthesis of various compounds. Its unique structure allows for further chemical reactions and modifications, leading to the creation of new molecules with different properties and applications.
Used in Flavor and Fragrance Industry:
Due to its distinct chemical structure, 2-Isopropylidene-5-methylcyclohexanone can be used as a component in the flavor and fragrance industry. It can contribute to the development of new scents and flavors, enhancing the sensory experience of various products.
Used in Research and Development:
The compound's unique properties make it an interesting subject for research and development in various scientific fields. It can be used to study the effects of different functional groups on the properties of organic compounds and to explore new reaction pathways and mechanisms.

InChI:InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3

Upstream product

• 91426-59-4 p-menth-8-en-3-one semicarbazone 
• 144-62-7 oxalic acid 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 
• 29606-79-9 isopulegone 
• 7732-18-5 water 
• 141-52-6 sodium ethanolate 
• 73210-25-0 2,2,5-Trimethyl-cyclohexanol 
• 5342-56-3 8-hydroxyamino-p-menthan-3-one 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 55179-48-1 (+)-(1R,4Ξ)-8-amino-p-menthan-3-one 
• 861590-26-3 8-isonitramino-p-menthan-3-one 
• 67-56-1 methanol 

Downstream Products

• 13368-65-5 (3R)-3-methylcyclohexanone 
• 67-64-1 acetone 
• 56764-09-1 2-isopropylidene-1,5-dimethyl-cyclohexanol 
• 3058-01-3 3-methyladipic acid 
• 56763-63-4 (-)-6-isopropylidene-1,3-dimethyl-cyclohexene; (-)-methylpulegene 
• 56763-63-4 6-isopropylidene-1,3-dimethyl-cyclohexene 
• 18369-31-8 1-ethyl-2-isopropylidene-5-methyl-cyclohexanol 
• 16206-43-2 (-)-2-methyl-2-((1Ξ,4R)-4-methyl-2-oxo-cyclohexyl)-propionic acid 
• 626-51-7 3-methyl glutaric acid 
• 597-43-3 2,2-dimethylsuccinic acid 
• 99-82-1 Menthane 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 529-02-2 isopulegol 
• 2216-51-5 (-)-menthol 

Relevant academic research and scientific papers

Regioselective silver-mediated Kondakov-Darzens olefin acylation

Enone construction: A silver-mediated olefin acylation reaction is described, in which five-, six-, and -seven-membered rings, tetrasubstituted olefins, bridged bicycles, spirocycles, and benzoxepinones are prepared. Highly selective intermolecular reactions are coupled to a Nazarov cyclization for the effective preparation of cyclopentenones, including the core of modhephene (see scheme). Copyright

Lipase-catalyzed resolution of p-menthan-3-ols monoterpenes: Preparation of the enantiomer-enriched forms of menthol, isopulegol, trans- and cis-piperitol, and cis-isopiperitenol

A study on the enzymic resolution of the most common p-menthan-3-ol monoterpene isomers is described. Enantioenriched alcohols 1, 5, 10, 11 and 12 are obtained by means of the lipase-mediated kinetic acetylation of the corresponding racemic materials. The stereochemical aspects of the enzymic process have been investigated. We found that the structural features of the starting p-menthan-3-ol as well as the kind of lipase used, impacted strongly on the enantioselectivity of the resolution. The potentialities of this approach for preparative purposes are discussed.

An efficient procedure for the preparation of (E)-α-alkylidenecycloalkanones mediated by a CeCl3·7H2O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone

2-Alkylidenecycloalkanones are powerful synthons used as the key intermediates in many important syntheses. Because of their potential, a general method of preparation from readily available starting materials, under very mild conditions, was considered to be worthwhile. Cerium(III) chloride heptahydrate in combination with sodium iodide in refluxing acetonitrile promotes a regio- and stereoselective β-elimination reaction to (E)-2-alkylidenecycloalkanones in 2-(1-hydroxyalkyl)cycloalkanones. The synthetic value of the present procedure is demonstrated by the synthesis of monoterpene (S)-(-)-pulegone (8) in its optically active form.

A versatile cobalt(II)-Schiff base catalyzed oxidation of organic substrates with dioxygen: Scope and mechanism

Cobalt(II) complex 1a-f derived from Schiff bases act as efficient catalysts during the oxidation of wide range of organic substrates(e.g. alkenes, alcohols, benzylic compounds and aliphatic hydrocarbons) with dioxygen in the presence of aliphatic aldehydes or ketones or ketoesters. EPR studies on 1a-f complexes suggest that the aliphatic carbonyl compounds promote the formation of a cobalt(II)-superoxo species responsible for the oxidation of organic compounds. These studies also demonstrate the role of ligands on cobalt in controlling the chemoselectivity of these oxidations. A plausible mechanistic rational is also provided for these oxidations.

Regio- and enantio-selective enolisations of cyclic ketones using chiral lithium amide bases

Enolisations of 3-methylcyclohexanone 16, and of a trans-fused perhydroisoquinolone derivative 8, using several chiral lithium amide bases have been examined.In reactions involving a single enantiomer of the ketone 8, the use of a chiral base can result in enhancement or reversal of the normal regioselectivity of enolisation to give the enol silane derivatives 9 and 10, depending on the configuration of the base used.Similar matched and mismatched results are observed when (R)-3-methylcyclohexanone, (R)-16, is treated with either enantiomer of the chiral base 3.A new type of kinetic resolution, termed regiodivergent resolution, is observed when enolisation of the racemic ketones 8 or 16 is carried out using the chiral base 3.

Cobalt catalyzed oxidation of secondary alcohols with dioxygen in the presence of 2-methylpropanal

Cobalt schiff base complex 2 catalyses the oxidation of a wide range of secondary alcohols to the corresponding ketones in the presence of dioxygen and 2-methylpropanal.

Cobalt(II) Schiffs base complex catalysed oxidation of alcohols with dioxygen in the presence of ethyl 2-oxocyclopentanecarboxylate

Cobalt(II) Schiffs base complex 1 catalyses the oxidation of primary and secondary alcohols to aldehydes and ketones respectively, in the presence of dioxygen and ethyl 2-oxocyclopentanecarboxylate 2 at 60-70° C.

Potassium Chlorochromate on a Solid Support: A Convenient and Mild Reagent for the Oxidation of Alcohols

The oxidation of primary and secondary alcohols by potassium chlorochromate supported on alumina or silica gel is reported.The results indicate that the yields in some cases depend on the support medium.Benzylic and secondary alcohols are oxidized in the best yields.The effect of solvent on the reaction is discussed and the conclusion is drawn that the best yields are obtained in non-polar solvents.

Oxidation of Alcohols with Potassium Chlorochromate

Potassium chlorochromate, KCrClO3, (KCC) is a versatile and inexpensive oxidation reagent.It converts secondary saturated, as well as allylic and benzylic alcohols to the corresponding carbonyl compounds in high yields in a variety of solvents, preferentially acetone.The reagent is highly selective.Thus, oxidation of primary alcohols gives aldehydes as the exclusive products.KCC is less useful for the transformation of primary saturated and homoallylic alcohols.Double bonds are susceptible to isomerization under the reaction conditions employed; for example, oxidati on of pure nerol yields citral, and pulegol is converted to a mixture of pulegone and isopulegone.Oxidation of tertiary allylic alcohols may give the transposed aldehyde.Thus, linalool is converted to citral in high yield.

A MILD HYDROGENOLYTIC-HYDROLYTIC CONVERSION OF OXIMES TO CARBONYL COMPOUNDS.

Oximes are converted into the corresponding carbonyl compounds in high yields using Raney-nickel and sodium hypophosphite at pH 5.