29474-12-2

Usage

InChI:InChI=1/C10H20O/c1-8(2)10(11)9-6-4-3-5-7-9/h8-11H,3-7H2,1-2H3

Upstream product

• 78-84-2 isobutyraldehyde 
• 931-50-0 cyclohexylmagnesium bromide 
• 90334-44-4 N-Cyclohexylidene-N'-(diphenyl-pyridin-4-yl-methyl)-hydrazine 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 108-94-1 cyclohexanone 
• 611-70-1 phenyl isopropyl ketone 
• 67-56-1 methanol 
• 1193-81-3 rac-1-cyclohexylethanol 
• 1125-71-9 1-cyclohexyl-2-methylpropan-1-one 
• 155397-15-2 1,1-biscyclohexanemethanol 
• 503606-98-2 1-cyclohexyl-1-[dimethyl(phenyl)silyl]-1-[dimethyl(phenyl)silyloxy]-2-methylpropane 
• 62039-08-1 (1-Cyclohexyl-2-methyl-propoxy)-diethyl-silane 

Downstream Products

• 1125-71-9 1-cyclohexyl-2-methylpropan-1-one 

Relevant academic research and scientific papers

Manganese(I)-Catalyzed β-Methylation of Alcohols Using Methanol as C1 Source

Highly selective β-methylation of alcohols was achieved using an earth-abundant first row transition metal in the air stable molecular manganese complex [Mn(CO)2Br[HN(C2H4PiPr2)2]] 1 ([HN(C2H4PiPr2)2]=MACHO-iPr). The reaction requires only low loadings of 1 (0.5 mol %), methanolate as base and MeOH as methylation reagent as well as solvent. Various alcohols were β-methylated with very good selectivity (>99 %) and excellent yield (up to 94 %). Biomass derived aliphatic alcohols and diols were also selectively methylated on the β-position, opening a pathway to “biohybrid” molecules constructed entirely from non-fossil carbon. Mechanistic studies indicate that the reaction proceeds through a borrowing hydrogen pathway involving metal–ligand cooperation at the Mn-pincer complex. This transformation provides a convenient, economical, and environmentally benign pathway for the selective C?C bond formation with potential applications for the preparation of advanced biofuels, fine chemicals, and biologically active molecules.

Selective hydrogenation of aromatic compounds using modified iridium nanoparticles

Till now, Ionic liquid-stabilized metal nanoparticles were investigated as catalytic materials, mostly in the hydrogenation of simple substrates like olefins or arenes. The adjustable hydrogenation products of aromatic compounds, including quinoline and relevant compounds, aromatic nitro compounds, aromatic ketones as well as aromatic aldehydes, are always of special interest, since they provide more choices for additional derivatization. Iridium nanoparticles (Ir NPs) were synthesized by the H2 reduction in imidazolium ionic liquid. TEM indicated that the Ir NPs is worm-like shape with the diameter around 12.2?nm and IR confirmed the modification of phosphine-functionalized ionic liquids (PFILs) to the Ir NPs. With the variation of the modifier, solvent and reaction temperature, substrate like quinoline and relevant compounds, aromatic nitro compounds, aromatic ketones as well as aromatic aldehydes could be hydrogenated by Ir NPs with interesting adjustable catalytic activity and chemoselectivity. Ir NPs modified by PFILs are simple and efficient catalysts in challenging chemoselective hydrogenation of quinoline and relevant compounds, aromatic nitro compounds, aromatic ketones as well as aromatic aldehydes. The activity and chemoselectivity of the Ir NPs could be obviously impacted or adjusted by altering the modifier, solvent and reaction temperature.

Tuning the chemoselective hydrogenation of aromatic ketones, aromatic aldehydes and quinolines catalyzed by phosphine functionalized ionic liquid stabilized ruthenium nanoparticles

Ruthenium nanoparticles (Ru NPs) stabilized by phosphine-functionalized ionic liquids (PFILs) were synthesized in an imidazolium-based ionic liquid using H2 as a reductant. Characterization showed well-dispersed particles of about 2.2 nm (TEM) and confirmed the PFIL stabilization of the Ru NPs (NMR). The Ru NPs stabilized by PFILs exhibited excellent activity and switchable chemoselectivity in the heterogeneous selective hydrogenation of aromatic ketones, aromatic aldehydes and quinolines under mild conditions.

Tuning the selectivity in the hydrogenation of aromatic ketones catalyzed by similar ruthenium and rhodium nanoparticles

Ru and Rh nanoparticles (NPs) RuI, RuII, RhI and RhII, stabilised by triphenylphosphine (PPh3) and diphenylphosphinobutane (dppb) were synthesised, characterised and applied as catalysts in the hydrogenation of several aromatic ketones. The effects of the nature of the metal and of the stabilising agent on the aryl versus ketone hydrogenation were studied. For RhNPs, the coordination of arene dominates the interaction of the substrate with the NP, whereas the coordination of the ketone group was not evidenced. For RuNPs, however, the results show that both arene and ketone coordinate to the NPs surface in a competitive manner. The properties of the stabilising ligands have a clear influence on the outcome of the reaction, and for the Rh-catalysed reactions, products of hydrogenolysis were only formed if PPh3 was used as the stabiliser. The structure of the substrate was also a key factor for the selectivity.

1,1-Disilyl alcohols as d1 synthons: Harnessing the 1,2-Brook rearrangement

1,1-Disilyl alcohols like 6 give the silyl ethers like 9 on treatment with base and alkyl halides, in a reaction which may be formulated as the alkylation of the Brook-rearranged carbanion 8. The products can be oxidised to give ketones like 10, showing that this Brook-rearranging system supplies a controlled d1 synthon of the acyl anion class. The alcohols can be prepared from the acid chloride 12 and dimethyl(phenyl)silyllithium, but the intermediate anion 21 need not be worked up; it can be used directly in the alkylation step.

AZO ANIONS IN SYNTHESIS. USE OF TRITYL- AND DIPHENYL-4-PYRIDYLMETHYLHYDRAZONES FOR REDUCTIVE C-C BOND FORMATION.

The lithium salts of trityl- and diphenyl-4-pyridylmethyl-hydrazones of both aldehydes and ketones react with electrophiles (alkyl halides, aldehydes, ketones, crotonates) at low temperature to form C-trapped azo compounds; these intermediates decompose homolytically with loss of nitrogen below room temperature and can be diverted in a synthetically useful way to alkanes, alkenes, alcohols or saturated esters.

Azo Anions in Synthesis. Use of Trityl- and Diphenyl-4-pyridylmethyl-hydrazones for Reductive C-C Bond Formation from Aldehydes and Ketones

The lithium salts for trityl- and diphenyl-4-pyridylmethyl-hydrazones of both aldehydes and ketones react with electrophiles (alkyl halides, aldehydes, and ketones) at low temperature to form C-trapped azo compounds; these intermediates decompose homolytically with loss of nitrogen below room temperature and can be diverted in a synthetically useful way to alkanes, or alkenes, or alcohols.