945-49-3

Usage

Uses

Used in Fragrance Industry:
Cyclohexyl(phenyl)methanol is used as a fragrance ingredient for its aromatic properties, contributing to the scent profiles of various consumer products such as perfumes, colognes, and other scented items.
Used in Flavoring Industry:
In the flavoring industry, Cyclohexyl(phenyl)methanol serves as a flavoring agent, enhancing the taste of food and beverages by providing a unique flavor profile.
Used in Pharmaceutical Industry:
Cyclohexyl(phenyl)methanol is utilized as a pharmaceutical intermediate, playing a crucial role in the synthesis of various medicinal compounds, thereby contributing to the development of new drugs.
Used as a Solvent:
Cyclohexyl(phenyl)methanol is employed as a solvent in various chemical processes, facilitating the dissolution of other substances and enabling reactions to occur more efficiently.
Used as a Catalyst:
In chemical reactions, Cyclohexyl(phenyl)methanol functions as a catalyst, accelerating the rate of reactions without being consumed in the process, thus enhancing the efficiency of the overall process.
Used in Chemical Intermediates:
Cyclohexyl(phenyl)methanol is used as a chemical intermediate in the manufacturing of other organic compounds, serving as a building block for the synthesis of a wide range of chemical products.

InChI:InChI=1/C13H18O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1,3-4,7-8,12-14H,2,5-6,9-10H2

Upstream product

• 60-29-7 diethyl ether 
• 712-50-5 Cyclohexyl phenyl ketone 
• 931-51-1 cyclohexylmagnesiumchloride 
• 100-52-7 benzaldehyde 
• 591-50-4 iodobenzene 
• 2043-61-0 cyclohexanecarbaldehyde 
• 934-56-5 trimethyl(phenyl)stannane 
• 3894-09-5 2-cyclohexyl-2-phenylacetic acid 
• 98-80-6 phenylboronic acid 
• 16224-09-2 benzyl cyclohexyl ether 
• 36140-19-9 dicyclohexylboron chloride 
• 626-62-0 Cyclohexyl iodide 
• 2996-92-1 phenyl trimethylsiloxane 
• 100-44-7 benzyl chloride 

Downstream Products

• 1608-31-7 (cyclohexylidenemethyl)benzene 
• 712-50-5 Cyclohexyl phenyl ketone 
• 4714-09-4 1-benzylcyclohexene 
• 28047-23-6 (chloro-cyclohexyl-methyl)benzene 
• 1889-38-9 [2-(cyclohexyl-phenyl-methoxy)-ethyl]-dimethyl-amine 
• 128126-03-4 (3,5-Dinitro-phenyl)-carbamic acid (R)-cyclohexyl-phenyl-methyl ester 
• 128126-03-4 (3,5-Dinitro-phenyl)-carbamic acid (S)-cyclohexyl-phenyl-methyl ester 
• 116211-30-4 (bromo(cyclohexyl)methyl)benzene 
• 126979-61-1 cyclohexyl(methoxy)phenylmethane 
• 39695-28-8 α-Cyclohexyl-benzyl-hexyl-aether 
• 1193397-35-1 R-cyclohexyl(phenyl)methanol acetate 
• 945-49-3 (S)-cyclohexylphenylmethanol 
• 945-49-3 (R)-cyclohexylphenylmethanol 
• 1191238-77-3 2-(cyclohexyl(phenyl)methoxy)-pyridine 

Relevant academic research and scientific papers

Production of enantiomerically enriched chiral carbinols using whole-cell biocatalyst

Biocatalytic asymmetric reduction of ketone is an efficient method for the production of chiral carbinols. The study indicates selective bioreduction of different ketones (1–8) to their respective (R)-alcohols (1a–8a) in low to high selectivity (0- >99%) with good yields (11–96%). In this work, whole-cell of Lactobacillus kefiri P2 catalysed enantioselective reduction of various prochiral ketones was investigated. (R)-4-Phenyl-2-butanol 2a, which is used as a precursor to antihypertensive agents and spasmolytics (anti-epileptic agents), was obtained using L kefiri P2 in 99% conversion and 91% enantiomeric excess (ee). Moreover, bioreduction of 2-methyl-1-phenylpropan-1-one substrate 8, containing a branched alkyl chain and difficult to asymmetric reduction with chemical catalysts as an enantioselective, to (R)-2-methyl-1-phenylpropan-1-ol (8a) in enantiomerically pure form was carried out in excellent yield (96%). The gram-scale production was carried out, and 9.70 g of (R)-2-methyl-1-phenylpropan-1-ol (8a) in enantiomerically pure form was obtained in 96% yield. Also especially, the yield and gram scale of (R)-2-methyl-1-phenylpropan-1-ol (8a) synthesised through catalytic asymmetric reduction using the biocatalyst was the highest report so far. The efficiency of L kefiri P2 for the conversion of the substrates and ee of products were markedly influenced by the steric factors of the substrates. This is a cheap, clean and eco-friendly process for production of chiral carbinols compared to chemical processes.

Bio-inspired asymmetric aldehyde arylations catalyzed by rhodium-cyclodextrin self-inclusion complexes

Transition-metal catalysts are powerful tools for carbon-carbon bond-forming reactions that are difficult to achieve using native enzymes. Enzymes that exhibit inherent selectivities and reactivities through host-guest interactions have inspired widesprea

Manganese catalyzed asymmetric transfer hydrogenation of ketones

The asymmetric transfer hydrogenation (ATH) of a wide range of ketones catalyzed by manganese complex as well as chiral PxNy-type ligand under mild conditions was investigated. Using 2-propanol as hydrogen source, various ketones could be enantioselectively hydrogenated by combining cheap, readily available [MnBr(CO)5] with chiral, 22-membered macrocyclic ligand (R,R,R',R')-CyP2N4 (L5) with 2 mol% of catalyst loading, affording highly valuable chiral alcohols with up to 95% ee.

Visible Light Induced Reduction and Pinacol Coupling of Aldehydes and Ketones Catalyzed by Core/Shell Quantum Dots

We present an efficient and versatile visible light-driven methodology to transform aryl aldehydes and ketones chemoselectively either to alcohols or to pinacol products with CdSe/CdS core/shell quantum dots as photocatalysts. Thiophenols were used as proton and hydrogen atom donors and as hole traps for the excited quantum dots (QDs) in these reactions. The two products can be switched from one to the other simply by changing the amount of thiophenol in the reaction system. The core/shell QD catalysts are highly efficient with a turn over number (TON) larger than 4 × 104 and 4 × 105 for the reduction to alcohol and pinacol formation, respectively, and are very stable so that they can be recycled for at least 10 times in the reactions without significant loss of catalytic activity. The additional advantages of this method include good functional group tolerance, mild reaction conditions, the allowance of selectively reducing aldehydes in the presence of ketones, and easiness for large scale reactions. Reaction mechanisms were studied by quenching experiments and a radical capture experiment, and the reasons for the switchover of the reaction pathways upon the change of reaction conditions are provided.

Metal-Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols

Chemoselective deoxygenation of carbonyls and alcohols using hydrogen by heterogeneous base-metal catalysts is crucial for the sustainable production of fine chemicals and biofuels. We report an aluminum metal-organic framework (DUT-5) node support cobalt(II) hydride, which is a highly chemoselective and recyclable heterogeneous catalyst for deoxygenation of a range of aromatic and aliphatic ketones, aldehydes, and primary and secondary alcohols, including biomass-derived substrates under 1 bar H2. The single-site cobalt catalyst (DUT-5-CoH) was easily prepared by postsynthetic metalation of the secondary building units (SBUs) of DUT-5 with CoCl2 followed by the reaction of NaEt3BH. X-ray photoelectron spectroscopy and X-ray absorption near-edge spectroscopy (XANES) indicated the presence of CoII and AlIII centers in DUT-5-CoH and DUT-5-Co after catalysis. The coordination environment of the cobalt center of DUT-5-Co before and after catalysis was established by extended X-ray fine structure spectroscopy (EXAFS) and density functional theory. The kinetic and computational data suggest reversible carbonyl coordination to cobalt preceding the turnover-limiting step, which involves 1,2-insertion of the coordinated carbonyl into the cobalt-hydride bond. The unique coordination environment of the cobalt ion ligated by oxo-nodes within the porous framework and the rate independency on the pressure of H2 allow the deoxygenation reactions chemoselectively under ambient hydrogen pressure.

Ir(NHC)-Catalyzed Synthesis of β-Alkylated Alcohols via Borrowing Hydrogen Strategy: Influence of Bimetallic Structure

Multi N-heterocyclic carbene(NHC)-modified iridium catalysts were employed in the β-alkylation of alcohols; dimerization of primary alcohols (Guerbet reaction), cross-coupling of secondary and primary alcohols, and intramolecular cyclization of alcohols. Mechanistic studies of Guerbet reaction, including kinetic experiments, mass analysis, and density functional theory (DFT) calculation, were employed to explain the fast reaction promoted by bimetallic catalysts, and the dramatic reactivity increase of monometallic catalysts at the late stage of the reaction. (Figure presented.).

Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki–Miyaura-Coupling and Transfer-Hydrogenation Cascade

We report a means to achieve the addition of two disparate nucleophiles to the amide carbonyl carbon in a single operational step. Our method takes advantage of non-precious-metal catalysis and allows for the facile conversion of amides to chiral alcohols via a one-pot Suzuki–Miyaura cross-coupling/transfer-hydrogenation process. This study is anticipated to promote the development of new transformations that allow for the conversion of carboxylic acid derivatives to functional groups bearing stereogenic centers via cascade processes.

Synthesis of cis-1,2-diol-type chiral ligands and their dioxaborinane derivatives: Application for the asymmetric transfer hydrogenation of various ketones and biological evaluation

Two cis-1,2-diol-type chiral ligands (T1 and T2) and their tri-coordinated chiral dioxaborinane (T(1–2)B(1–2)) and four-coordinated chiral dioxaborinane adducts with 4-tert-butyl pyridine sustained by N → B dati

Chiral amino-pyridine-phosphine tridentate ligand, manganese complex, and preparation method and application thereof

The invention discloses a chiral amino-pyridine-phosphine tridentate ligand, a manganese complex, and a preparation method and application thereof. The chiral amino-pyridine-phosphine tridentate ligand is shown as a formula II, and the manganese complex of the chiral amino-pyridine-phosphine tridentate ligand can be used for efficiently catalyzing and hydrogenating ketone compounds to prepare chiral alcohol compounds in a high enantioselectivity mode. The chiral amino-pyridine-phosphine tridentate ligand and the manganese complex are simple in synthesis process, good in stability, high in catalytic activity and mild in reaction conditions.

RETRACTED ARTICLE: The Manganese(I)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege

The bis(carbonyl) manganese(I) complex [Mn(CO)2(1)]Br (2) with a chiral (NH)2P2 macrocyclic ligand (1) catalyzes the asymmetric transfer hydrogenation of polar double bonds with 2-propanol as the hydrogen source. Ketones (43 substrates) are reduced to alcohols in high yields (up to >99 %) and with excellent enantioselectivities (90–99 % ee). A stereochemical model based on attractive CH–π interactions is proposed.