1124-63-6

Usage

Uses

Used in Chemical Synthesis:
3-Cyclohexyl-1-propanol is used as a key intermediate in the synthesis of various compounds, such as 3-cyclohexylpropyl caffeate, through trans-esterification reactions catalyzed by enzymes like Candida antarctica lipase B. This application takes advantage of its chemical reactivity and ability to form esters with other molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Cyclohexyl-1-propanol may be used as a building block for the development of new drugs or as a solvent in the synthesis of active pharmaceutical ingredients. Its chemical properties make it suitable for these purposes, potentially contributing to the creation of novel medications.
Used in Flavor and Fragrance Industry:
Given its compatibility with other organic compounds, 3-Cyclohexyl-1-propanol can be employed in the flavor and fragrance industry as a component in the creation of various scents and flavors. Its ability to dissolve and interact with other molecules makes it a valuable asset in this field.
Used in Cosmetics and Personal Care Industry:
3-Cyclohexyl-1-propanol may also find use in the cosmetics and personal care industry, where it can serve as a solvent or emollient in the formulation of various products such as creams, lotions, and perfumes. Its clear and colorless nature makes it an ideal candidate for these applications.
Used in Industrial Applications:
In industrial settings, 3-Cyclohexyl-1-propanol can be utilized as a solvent or additive in the production of various materials, including coatings, adhesives, and elastomers. Its viscous nature and compatibility with other substances make it a versatile component in these applications.

InChI:InChI=1/C9H18O/c10-8-4-7-9-5-2-1-3-6-9/h9-10H,1-8H2

Upstream product

• 10094-36-7 ethyl 3-cyclohexylpropanoate 
• 104-54-1 3-Phenylpropenol 
• 104-55-2 3-phenyl-propenal 
• 701-97-3 cyclohexanepropionic acid 
• 2705-87-5 allyl 3-cyclohexylpropionate 
• 60210-93-7 3-(cyclohex-2-enyl)propionaldehyde 
• 110-82-7 cyclohexane 
• 107-18-6 allyl alcohol 
• 695-12-5 vinylcyclohexane 
• 201230-82-2 carbon monoxide 
• 39972-78-6 allyl t-butyl peroxide 
• 931-51-1 cyclohexylmagnesiumchloride 
• 132350-01-7 2-(1-chloro-2-propenyl)-1,3,2-dioxaborinane 
• 108-93-0 cyclohexanol 

Downstream Products

• 1678-91-7 ethyl-cyclohexane 
• 34094-21-8 (3-bromopropyl)cyclohexane 
• 4361-28-8 3-cyclohexylpropanal 
• 3664-30-0 phenyl-carbamic acid-(3-cyclohexyl-propyl ester) 
• 1129-67-5 cyclohexylpropyl formate 
• 1168-85-0 Di-(3-cyclohexylpropyl)-malonat 
• 41289-62-7 (2-Chloro-ethyl)-bis-(3-cyclohexyl-propoxy)-methyl-silane 
• 39753-14-5 Methyl-thiophosphoramidic acid O-(3-cyclohexyl-propyl) ester O'-(2,2-dichloro-vinyl) ester 
• 152754-34-2 3-cyclohexyl-1-propyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-piperidinecarboxylate 
• 701-97-3 cyclohexanepropionic acid 
• 60416-24-2 3-cyclohexylpropyl acetate 
• 557112-42-2 cyclohexylpropyl acetoacetate 
• 144290-77-7 N-[3-cyclohexylprop-1-yl]phthalimide 
• 1678-92-8 propylcyclohexane 

Relevant academic research and scientific papers

Catalytic hydrogenation of cinnamic acid and salicylic acid

Hydrogenation of cinnamic acid and salicylic acid was carried out using 5 %Ru/C, 5 % Pd/C and Ru-Sn/Al2O3 catalyst at 493 K and 6.89 MPa of hydrogen partial pressure. Ru-Sn/Al2O3 catalyst was found to be active for hydrogenation -COOH group to give cinnamyl alcohol. The selectivity to cinnamyl alcohol was low (15 %) as absolute inhibition of C=C bond hydrogenation in cinnamic acid is challenging. 5 %Pd/C catalyst was found to hydrogenate C=C bond and aromatic ring in cinnamic acid. 5 %Ru/C catalyst was found to be least selective catalyst as it hydrogenated C=C bond, aromatic ring and -COOH group in cinnamic acid. Hydrogenation of salicylic acid is not possible at 493 K as decarboxylation of salicylic acid occurs.

Hydrosilylation of carbonyl and carboxyl groups catalysed by Mn(i) complexes bearing triazole ligands

Manganese(i) complexes bearing triazole ligands are reported as catalysts for the hydrosilylation of carbonyl and carboxyl compounds. The desired reaction proceeds readily at 80 °C within 3 hours at catalyst loadings as low as 0.25 to 1 mol%. Hence, good to excellent yields of alcohols could be obtained for a wide range of substrates including ketones, esters, and carboxylic acids illustrating the versatility of the metal/ligand combination.

Palladium(II)-Catalyzed Enantioselective Arylation of Unbiased Methylene C(sp3)?H Bonds Enabled by a 2-Pyridinylisopropyl Auxiliary and Chiral Phosphoric Acids

Enantioselective functionalizations of unbiased methylene C(sp3)?H bonds of linear systems by metal insertion are intrinsically challenging and remain a largely unsolved problem. Herein, we report a palladium(II)-catalyzed enantioselective arylation of unbiased methylene β-C(sp3)?H bonds enabled by the combination of a strongly coordinating bidentate PIP auxiliary with a monodentate chiral phosphoric acid (CPA). The synergistic effect between the PIP auxiliary and the non-C2-symmetric CPA is crucial for effective stereocontrol. A broad range of aliphatic carboxylic acids and aryl bromides can be used, providing β-arylated aliphatic carboxylic acid derivatives in high yields (up to 96 %) with good enantioselectivities (up to 95:5 e.r.). Notably, this reaction also represents the first palladium(II)-catalyzed enantioselective C?H activation with less reactive and cost-effective aryl bromides as the arylating reagents. Mechanistic studies suggest that a single CPA is involved in the stereodetermining C?H palladation step.

TRICYCLIC COMPOUND SERVING AS IMMUNOMODULATOR

Provided are compounds of formula I and formula II or pharmaceutically acceptable salts of the compounds and pharmaceutical compositions thereof. The compounds of formula I and formula II or the pharmaceutically acceptable salts of the compounds provide indole 2,3-dioxygenase (IDO) inhibitory activity and are capable of treating IDO-mediated immunosuppressive diseases, such as infectious diseases or cancer.

Polysilane-Immobilized Rh-Pt Bimetallic Nanoparticles as Powerful Arene Hydrogenation Catalysts: Synthesis, Reactions under Batch and Flow Conditions and Reaction Mechanism

Hydrogenation of arenes is an important reaction not only for hydrogen storage and transport but also for the synthesis of functional molecules such as pharmaceuticals and biologically active compounds. Here, we describe the development of heterogeneous Rh-Pt bimetallic nanoparticle catalysts for the hydrogenation of arenes with inexpensive polysilane as support. The catalysts could be used in both batch and continuous-flow systems with high performance under mild conditions and showed wide substrate generality. In the continuous-flow system, the product could be obtained by simply passing the substrate and 1 atm H2 through a column packed with the catalyst. Remarkably, much higher catalytic performance was observed in the flow system than in the batch system, and extremely strong durability under continuous-flow conditions was demonstrated (>50 days continuous run; turnover number >3.4 × 105). Furthermore, details of the reaction mechanisms and the origin of different kinetics in batch and flow were studied, and the obtained knowledge was applied to develop completely selective arene hydrogenation of compounds containing two aromatic rings toward the synthesis of an active pharmaceutical ingredient.

TiO2-Supported Re as a General and Chemoselective Heterogeneous Catalyst for Hydrogenation of Carboxylic Acids to Alcohols

TiO2-supported Re, Re/TiO2, was found to promote selective hydrogenation of carboxylic acids having aromatic and aliphatic moieties to the corresponding alcohols. Re/TiO2showed superior results compared to other transition-metal-loaded TiO2and supported Re catalysts for selective hydrogenation of 3-phenylpropionic acid. 3-phenylpropanol was produced in 97 % yield under mild conditions (5 MPa H2at 140 °C). Contrary to typical heterogeneous catalysts, Re/TiO2does not lead to the formation of dearomatized byproducts. The catalyst is recyclable and shows a wide substrate scope in the synthesis of alcohols (22 examples; up to 97 % isolated yield).

On the Reactivity of Dihydro-p-coumaryl Alcohol towards Reductive Processes Catalyzed by Raney Nickel

There are several established approaches for the reductive fractionation of lignocellulose (e.g., “catalytic upstream biorefining” and “lignin-first” approaches) that lead to a lignin oil product that is composed primarily of dihydro-p-monolignols [e.g., 4-(3-hydroxypropyl)-2-methoxyphenol and 4-(3-hydroxypropyl)-2,6-dimethoxyphenol]. Although effective catalytic methods have been developed to perform reductive or deoxygenative processes on the lignin oil, the influence of the 3-hydroxypropyl substituent on catalyst activity has previously been overlooked. Herein, to better understand the reactivity of the depolymerized lignin oil obtained from catalytic upstream biorefining processes, dihydro-p-coumaryl alcohol was selected as a model compound. Hydrogenation of this species in the presence of Raney Ni with molecular hydrogen led to ring saturation (100 % selectivity) in the absence of hydrodeoxygenation, whereas under hydrogen-transfer conditions with 2-propanol, hydrogenation occurred (≈55 % selectivity) simultaneously with hydrodeoxygenation (≈40 % selectivity). In a broader context, this study sheds light not only on the reactivity of dihydro-p-monolignols but also on the intricacies of the catalytic upstream biorefining reaction network in which these species are revealed to be key intermediates in the formation of less-functionalized p-alkylphenols.

Rhenium-Loaded TiO2: A Highly Versatile and Chemoselective Catalyst for the Hydrogenation of Carboxylic Acid Derivatives and the N-Methylation of Amines Using H2 and CO2

Herein, we report a heterogeneous TiO2-supported Re catalyst (Re/TiO2) that promotes various selective hydrogenation reactions, which includes the hydrogenation of esters to alcohols, the hydrogenation of amides to amines, and the N-methylation of amines, by using H2 and CO2. Initially, Re/TiO2 was evaluated in the context of the selective hydrogenation of 3-phenylpropionic acid methyl ester to afford 3-phenylpropanol (pH2 =5 MPa, =5 MPa, T=180 °C), which revealed a superior performance over other catalysts that we tested in this study. In contrast to other typical heterogeneous catalysts, hydrogenation reactions with Re/TiO2 did not produce dearomatized byproducts. DFT studies suggested that the high selectivity for the formation of alcohols in favor of the hydrogenation of aromatic rings is ascribed to the higher affinity of Re towards the COOCH3 group than to the benzene ring. Moreover, Re/TiO2 showed a wide substrate scope for the hydrogenation reaction (19 examples). Subsequently, this Re/TiO2 catalyst was applied to the hydrogenation of amides, the N-methylation of amines, and the N-alkylation of amines with carboxylic acids or esters.

Catalytic Hydrogenation of Arenes in Water Over In Situ Generated Ruthenium Nanoparticles Immobilized on Carbon

We describe a tandem process to generate active Ru nanoparticles (≈7 nm) immobilised in situ on carbon from an organometallic precursor and formic acid to afford the hydrogenation of a wide range of arenes and heteroarenes in yields up to 72 % with high conversions and selectivities for the desired products. The hydrogenation of several substrates analogous to lignin-derived fragments to the corresponding alicyclic products was also achieved. Our experimental investigations evidenced that the observed enhanced activity for arene hydrogenation was driven by the unique structural advantages of the organometallic precursor to activate formic acid, in which the presence of a nitrogen ligand is crucial to achieve a high catalytic activity. TEM analysis revealed the formation of Ru0 nanoparticles, and Hg0 poisoning experiments support the heterogeneous nature of the active catalyst.

Generation of Alkoxyl Radicals by Photoredox Catalysis Enables Selective C(sp3)-H Functionalization under Mild Reaction Conditions

Reported herein is the first visible-light-induced formation of alkoxyl radicals from N-alkoxyphthalimides, and the Hantzsch ester as the reductant is crucial for the reaction. The selective hydrogen atom abstraction by the alkoxyl radical enables C(sp3)-H allylation and alkenylation reactions under mild reaction conditions at room temperature. Broad substrate variations, including a structurally complexed steroid, undergo the C(sp3)-H functionalization reaction effectively with high regio- and chemoselectivity.