1462-27-7

Usage

Synthesis Reference(s)

Synthetic Communications, 8, p. 59, 1978 DOI: 10.1080/00397917808062184

InChI:InChI=1/C10H18O/c1-2-6-10(11)9-7-4-3-5-8-9/h9H,2-8H2,1H3

Upstream product

• 62039-12-7 1-cyclohexyl-1-butanol 
• 109-74-0 propyl cyanide 
• 931-50-0 cyclohexylmagnesium bromide 
• 931-51-1 cyclohexylmagnesiumchloride 
• 123-72-8 butyraldehyde 
• 7664-93-9 sulfuric acid 
• 103649-07-6 1-propyl-cyclohexanecarbaldehyde 
• 71-43-2 benzene 
• 18736-82-8 1-cyclohexyl-but-2-en-1-ol 
• 557-93-7 2-bromoprop-1-ene 
• 2043-61-0 cyclohexanecarbaldehyde 
• 93-91-4 1-phenylbutan-1,3-dione 
• 67-56-1 methanol 
• 1123-86-0 cyclohexyl ethyl ketone 

Downstream Products

• 4456-99-9 3-hexylcyclohexane 
• 35383-65-4 7-oxo-decanoic acid 
• 62039-12-7 1-cyclohexyl-1-butanol 
• 4352-42-5 (S)-1-cyclohexyl-1-butanol 
• 4352-42-5 (R)-1-cyclohexyl-1-butanol 

Relevant academic research and scientific papers

Iridium-catalyzed synthesis of β-methylated secondary alcohols using methanol

A general synthesis of β-methylated secondary alcohols via tandem α-methylation/transfer hydrogenation from non-methylated ketones with methanol by a Cp*Ir complex [Cp*Ir(2,2′-bpyO)(OH)]Na with a bipyridine-based functional ligand was reported. Remarkably, β-methylated secondary alcohols can be obtained under milder reaction conditions using methanol as the methylating agent (C1 source) by employing this catalytic system. A wide range of structurally diverse ketones bearing different functional groups was methylated and hydrogenated with excellent toleration in fair to high yields. This method provides a readily available and highly efficient route to β-methylated secondary alcohols using methanol.

Rh-Catalyzed Coupling of Aldehydes with Allylboronates Enables Facile Access to Ketones

We present herein a novel strategy for the preparation of ketones from aldehydes and allylic boronic esters. This reaction involves the allylation of aldehydes with allylic boronic esters and the Rh-catalyzed chain-walking of homoallylic alcohols. The key to this successful development is the protodeboronation of alkenyl borylether intermediate via a tetravalent borate anion species in the presence of KHF2 and MeOH. This approach features mild reaction conditions, broad substrate scope, and excellent functional group tolerance. Mechanistic studies also supported that the tandem allylation and chain-walking process were involved.

Selective Hydrogenation and Hydrodeoxygenation of Aromatic Ketones to Cyclohexane Derivatives Using a Rh&at;SILP Catalyst

Rhodium nanoparticles immobilized on an acid-free triphenylphosphonium-based supported ionic liquid phase (Rh&at;SILP(Ph3-P-NTf2)) enabled the selective hydrogenation and hydrodeoxygenation of aromatic ketones. The flexible molecular approach used to assemble the individual catalyst components (SiO2, ionic liquid, nanoparticles) led to outstanding catalytic properties. In particular, intimate contact between the nanoparticles and the phosphonium ionic liquid is required for the deoxygenation reactivity. The Rh&at;SILP(Ph3-P-NTf2) catalyst was active for the hydrodeoxygenation of benzylic ketones under mild conditions, and the product distribution for non-benzylic ketones was controlled with high selectivity between the hydrogenated (alcohol) and hydrodeoxygenated (alkane) products by adjusting the reaction temperature. The versatile Rh&at;SILP(Ph3-P-NTf2) catalyst opens the way to the production of a wide range of high-value cyclohexane derivatives by the hydrogenation and/or hydrodeoxygenation of Friedel–Crafts acylation products and lignin-derived aromatic ketones.

Manganese PNP-pincer catalyzed isomerization of allylic/homo-allylic alcohols to ketones-activity, selectivity, efficiency

We report the first manganese catalyzed isomerization of allylic alcohols to produce the corresponding carbonyl compounds. The ligand plays a decisive role in the efficiency of this reaction. Very high conversions could be obtained using a solvent-free reaction system. A detailed DFT study reveals a self-dehydrogenation/hydrogenation reaction mechanism which was verified by the isolation of the α,β-unsaturated ketone as intermediate and a deuterium labeling experiment. It also provided a rationale for the observed selectivity and the higher efficiency of phenyl over isopropyl substitution.

Additive-Free Isomerization of Allylic Alcohols to Ketones with a Cobalt PNP Pincer Catalyst

Catalytic isomerization of allylic alcohols in ethanol as a green solvent was achieved by using air and moisture stable cobalt (II) complexes in the absence of any additives. Under mild conditions, the cobalt PNP pincer complex substituted with phenyl groups on the phosphorus atoms appeared to be the most active. High rates were obtained at 120 °C, even though the addition of one equivalent of base increases the speed of the reaction drastically. Although some evidence was obtained supporting a dehydrogenation–hydrogenation mechanism, it was proven that this is not the major mechanism. Instead, the cobalt hydride complex formed by dehydrogenation of ethanol is capable of double-bond isomerization through alkene insertion–elimination.

Conversion of Aldehydes to Branched or Linear Ketones via Regiodivergent Rhodium-Catalyzed Vinyl Bromide Reductive Coupling-Redox Isomerization Mediated by Formate

A regiodivergent catalytic method for direct conversion of aldehydes to branched or linear alkyl ketones is described. Rhodium complexes modified by PtBu2Me catalyze formate-mediated aldehyde-vinyl bromide reductive coupling-redox isomerization to form branched ketones. Use of the less strongly coordinating ligand, PPh3, promotes vinyl-to allylrhodium isomerization en route to linear ketones. This method bypasses the 3-step sequence often used to convert aldehydes to ketones involving the addition of pre-metalated reagents to Weinreb or morpholine amides.

Isomerization of Allylic Alcohols to Ketones Catalyzed by Well-Defined Iron PNP Pincer Catalysts

[Fe(PNP)(CO)HCl] (PNP=di-(2-diisopropylphosphanyl-ethyl)amine), activated in situ with KOtBu, is a highly active catalyst for the isomerization of allylic alcohols to ketones without an external hydrogen supply. High reaction rates were obtained at 80 °C, but the catalyst is also sufficiently active at room temperature with most substrates. The reaction follows a self-hydrogen-borrowing mechanism, as verified by DFT calculations. An alternative isomerization through alkene insertion and β-hydride elimination could be excluded on the basis of a much higher barrier. In alcoholic solvents, the ketone product is further reduced to the saturated alcohol.

Et2Zn-mediated rearrangement of bromohydrins

(Chemical Equation Presented) A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH 2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.

Oxidation of Secondary Alcohols Using Raney Nickel

A high yield, one-step oxidation procedure has been developed for the selective oxidation of secondary alcohols.

Reactions of organoboranes and 2-lithio-2-alkyl-1,3-benzodithioles. A new, improved synthesis of ketones

Reactions of trialkylboranes with 2-lithio-2-alkyl-1,3-benzodithioles followed by oxidation give ketones in good yields. This method is far less subject to steric hindrance than the analogous reactions using anions derived from bis(phenylthio)alkanes.