1444-64-0

Usage

Uses

Used in Fragrance Industry:
2-Phenylcyclohexanol is used as a fragrance ingredient for its ability to impart a distinct scent to perfumes and personal care products, enhancing the sensory experience of these goods.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-Phenylcyclohexanol serves as a potential component, likely due to its chemical properties that can be harnessed for developing medicinal compounds or formulations.
Used as a Chemical Intermediate:
2-Phenylcyclohexanol is utilized as an intermediate in the synthesis of other chemicals, indicating its role in creating more complex molecules or products through further chemical reactions.
It is crucial to handle and store 2-Phenylcyclohexanol with care, as improper handling may result in irritation to the skin, eyes, and respiratory system, highlighting the importance of safety measures during its use and manipulation.

InChI:InChI=1/C12H16O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-3,6-7,11-13H,4-5,8-9H2

Upstream product

• 90-43-7 2-Phenylphenol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 822-87-7 2-Chlorocyclohexanone 
• 7732-18-5 water 
• 5775-23-5 1-phenylcyclohexene oxide 
• 132-64-9 dibenzofuran 
• 4829-01-0 (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide 
• 771-98-2 1-Phenylcyclohexene 
• 2362-61-0 trans-2-Phenylcyclohexanol 
• 108-86-1 bromobenzene 
• 100-58-3 phenylmagnesium bromide 
• 930-68-7 cyclohexenone 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 4556-09-6 2-phenylcyclohex-2-enone 

Downstream Products

• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 771-98-2 1-Phenylcyclohexene 
• 54852-67-4 2-(2-phenyl-cyclohexyloxy)-ethanol 
• 102954-60-9 2-Phenyl-6-(2-phenyl-cyclohexyl)-cyclohexanol 
• 908822-19-5 chloro-acetic acid-(2-phenyl-cyclohexyl ester) 
• 15232-96-9 3-phenyl-1-cyclohexene 
• 63476-56-2 1-acetoxy-2-phenylcyclohexane 

Relevant academic research and scientific papers

The design of novel N-4′-pyridinyl-α-methyl proline derivatives as potent catalysts for the kinetic resolution of alcohols

A novel family of chiral acylation catalysts based on a N-4′-pyridinyl-α-methyl proline structure has been studied. A set of 31 compounds has been easily prepared and screened in the kinetic resolution of racemic alcohol 33 resulting in high enantioselectivities in most cases. From results obtained, H-bonding interactions between the catalyst and the substrate would appear essential to afford high enantioselectivity during the catalytic acylation. Additional solvent dependence and anhydride studies have been made to better identify the mechanism. This work has been further extended to the study of a number of structurally different alcohols. Ethanolamine derivatives in particular were found to be highly effective substrates (up to S = 18.8) in the kinetic resolution.

Diastereoselective reduction of alkenylboronic esters as a new method for controlling the stereochemistry of up to three adjacent centers in cyclic and acyclic molecules

(figure presented) cis-Boronates are readily available via a diastereoselective Pd-catalyzed reduction of tetrasubstituted alkenylboronic esters using H2. Applying the reaction conditions presented to unsaturated open-chain boronic esters allows the stereochemistry of up to three adjacent centers to be controlled.

ARYLCYCLOHEXYLAMINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF PSYCHIATRIC DISORDERS

Provided herein are arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders.

PNO ligand containing planar chiral ferrocene and axial chiral diphenol and application thereof

The invention discloses a PNO ligand containing planar chiral ferrocene and axially chiral diphenol and application of the PNO ligand. The PNO ligand containing planar chiral ferrocene and axially chiral diphenol is shown in any one of general formulas (I)-(IV). Or a PNO ligand containing planar chiral ferrocene and axial chiral diphenol as shown in any one of general formulas (V)-(VIII); compared with a previously reported tridentate ligand, the PNO ligand containing the planar chiral ferrocene and the axial chiral diphenol not only has good stability and easiness in synthesis, but also has planar chirality and axial chirality and has a good chiral environment, so that not only is excellent selectivity to a substrate ensured, but also the catalytic activity of a catalyst and the application range of the substrate are further improved. The chiral raw materials used in the invention are commercial bulk products, and the ligand synthesis route is simpler, so that large-scale production can be well carried out, and the method has a huge commercial application prospect.

Erbium-Catalyzed Regioselective Isomerization-Cobalt-Catalyzed Transfer Hydrogenation Sequence for the Synthesis of Anti-Markovnikov Alcohols from Epoxides under Mild Conditions

Herein, we report an efficient isomerization-transfer hydrogenation reaction sequence based on a cobalt pincer catalyst (1 mol %), which allows the synthesis of a series of anti-Markovnikov alcohols from terminal and internal epoxides under mild reaction conditions (≤55 °C, 8 h) at low catalyst loading. The reaction proceeds by Lewis acid (3 mol % Er(OTf)3)-catalyzed epoxide isomerization and subsequent cobalt-catalyzed transfer hydrogenation using ammonia borane as the hydrogen source. The general applicability of this methodology is highlighted by the synthesis of 43 alcohols from epoxides. A variety of terminal (23 examples) and 1,2-disubstituted internal epoxides (14 examples) bearing different functional groups are converted to the desired anti-Markovnikov alcohols in excellent selectivity and yields of up to 98%. For selected examples, it is shown that the reaction can be performed on a preparative scale up to 50 mmol. Notably, the isomerization step proceeds via the most stable carbocation. Thus, the regiochemistry is controlled by stereoelectronic effects. As a result, in some cases, rearrangement of the carbon framework is observed when tri-and tetra-substituted epoxides (6 examples) are converted. A variety of functional groups are tolerated under the reaction conditions even though aldehydes and ketones are also reduced to the respective alcohols under the reaction conditions. Mechanistic studies and control experiments were used to investigate the role of the Lewis acid in the reaction. Besides acting as the catalyst for the epoxide isomerization, the Lewis acid was found to facilitate the dehydrogenation of the hydrogen donor, which enhances the rate of the transfer hydrogenation step. These experiments additionally indicate the direct transfer of hydrogen from the amine borane in the reduction step.

Method for preparing alcohol through reaction of Suzuki no exogenous alkali (by machine translation)

The method for synthesizing the alcohol compound by. using the method disclosed by the invention for preparing .the alcohol compound by adopting the method Suzuki disclosed by the invention has the advantages that the reaction system, is convenient and convenient, to prepare, and the reaction system is convenient to prepare . Suzuki. (by machine translation)

A Practical and Stereoselective In Situ NHC-Cobalt Catalytic System for Hydrogenation of Ketones and Aldehydes

Homogeneous catalytic hydrogenation of carbonyl groups is a synthetically useful and widely applied organic transformation. Sustainable chemistry goals require replacing conventional noble transition metal catalysts for hydrogenation by earth-abundant base metals. Herein, we report how a practical in situ catalytic system generated by easily available pincer NHC precursors, CoCl2, and a base enabled efficient and high-yielding hydrogenation of a broad range of ketones and aldehydes (over 50 examples and a maximum turnover number [TON] of 2,610). This is the first example of NHC-Co-catalyzed hydrogenation of C=O bonds using flexible pincer NHC ligands consisting of a N-H substructure. Diastereodivergent hydrogenation of substituted cyclohexanone derivatives was also realized by fine-tuning of the steric bulk of pincer NHC ligands. Additionally, a bis(NHCs)-Co complex was successfully isolated and fully characterized, and it exhibits excellent catalytic activity that equals that of the in-situ-formed catalytic system. Catalytic hydrogenation is a powerful tool for the reduction of organic compounds in both fine and bulk chemical industries. To improve sustainability, more ecofriendly, inexpensive, and earth-abundant base metals should be employed to replace the precious metals that currently dominate the development of hydrogenation catalysts. However, the majority of the base-metal catalysts that have been reported involve expensive, complex, and often air- and moisture-sensitive phosphine ligands, impeding their widespread application. From a mixture of the stable CoCl2, imidazole salts, and a base, our newly developed catalytic system that formed easily in situ enables efficient and stereoselective hydrogenation of C=O bonds. We anticipate that this easily accessible catalytic system will create opportunities for the design of practical base-metal hydrogenation catalysts. A practical in situ catalytic system generated by a mixture of easily available pincer NHC precursors, CoCl2, and a base enabled highly efficient hydrogenation of a broad range of ketones and aldehydes (over 50 examples and up to a turnover number [TON] of 2,610). Diastereodivergent hydrogenation of substituted cyclohexanone derivatives was also realized in high selectivities. Moreover, the preparation of a well-defined bis(NHCs)-Co complex via this pincer NHC ligand consisting of a N-H substructure was successful, and it exhibits equally excellent catalytic activity for the hydrogenation of C=O bonds.

(Poly)cationic λ3-Iodane-Mediated Oxidative Ring Expansion of Secondary Alcohols

Herein, a simplified approach to the synthesis of medium-ring ethers through the electrophilic activation of secondary alcohols with (poly)cationic λ3-iodanes (N-HVIs) is reported. Excellent levels of selectivity are achieved for C–O bond migration over established α-elimination pathways, enabled by the unique reactivity of a novel 2-OMe-pyridine-ligated N-HVI. The resulting hexafluoroisopropanol (HFIP) acetals are readily derivatized with a range of nucleophiles, providing a versatile functional handle for subsequent manipulations. The utility of this methodology for late-stage natural product derivatization was also demonstrated, providing a new tool for diversity-oriented synthesis and complexity-to-diversity (CTD) efforts. Preliminary mechanistic investigations reveal a strong effect of alcohol conformation on the reactive pathway, thus providing a predictive power in the application of this approach to complex molecule synthesis.

Directed β C-H Amination of Alcohols via Radical Relay Chaperones

A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.

Diastereoselective and enantioselective alkaline-hydrolysis of 2-aryl-1-cyclohexyl acetate: a CAL-B catalyzed deacylation/acylation tandem process

Candida antarctica lipase proved to be a particularly efficient lipase for the resolution of racemic 2-arylcyclohexyl acetate in hydrolysis reaction with Na2CO3 in an organic medium. The (1R,2S)-trans-2-arylcyclohexanols 2a–2d were obtained with high ee values (up to >99%) and the selectivity reached E > 200. The influence of the enol ester and the solvent on (±)-trans-2-arylcyclohexanol in the CAL-B catalyzed acylation was also studied and compared with the deacylation. The CAL-B exhibits a better affinity for the alkaline hydrolysis reaction compared with acylation with the enol esters in the same organic solvents. The best conditions were applied to resolve a stereoisomeric mixture cis/trans-2-phenyl-1-cyclohexanol and its corresponding acetate by acylation and deacylation. The obtained results show a highly enantio- and diastereoselectivity of the CAL-B during the acylation and the deacylation in favor of the trans-(R)-enantiomer product. The resolution of a mixture of cis/trans-2-arylcyclohexanols was an easy, convenient approach to provide only one stereoisomer of a mixture of four with high enantiomeric excess.