1884-42-0

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-Methoxyphenyl)cyclohexanol is used as a therapeutic agent for treating different forms of cancer. Its interaction with the NMDA receptor coupled PCP-binding site allows it to exhibit potential anticancer properties, making it a promising candidate for cancer treatment and research.

Upstream product

• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 108-94-1 cyclohexanone 
• 10365-98-7 3-methoxyphenylboronic acid 
• 2398-37-0 3-methoxyphenyl bromide 

Downstream Products

• 706793-32-0 1-(1-azidocyclohexyl)-3-(methyloxy)benzene 
• 43050-17-5 (+/-)-1-(3-Methoxy-phenyl)-7-oxa-bicyclo[4.1.0]heptane 
• 43050-31-3 2-(3-methoxyphenyl)cyclohex-2-en-1-ol 
• 125802-07-5 1-(3-methoxyphenyl)cyclohexan-1-amine 
• 1884-41-9 1-Cyclohex-1-enyl-3-methoxy-benzene 

Relevant academic research and scientific papers

Synthesis of 4H-1,3-Benzoxazines via Metal- and Oxidizing Reagent-Free Aromatic C-H Oxygenation

An unprecedented electrochemical aromatic C-H oxygenation reaction for the synthesis of 4H-1,3-benzoxazines from easily available N-benzylamides is reported. These oxidative cyclization reactions proceed in a transition metal- and oxidizing reagent-free fashion and produce H2 as only theoretical byproduct. Adapting the C-H oxygenation reaction in an electrochemical microreactor has been demonstrated.

Synthesis of methoxetamine, its metabolites and deuterium labelled analog as analytical standards and their HPLC and chiral capillary electrophoresis separation

Methoxetamine, a designer drug marketed as a replacement for the dissociative anaesthetic ketamine, has been associated with significant numbers of hospital related intoxications and deaths in Europe. The fast and user-friendly identification and quantification of methoxetamine and its metabolites is a key factor for successful treatment of intoxication. Therefore, we suggested a convenient preparation method which was used for the synthesis of methoxetamine, seven methoxetamine metabolites and a deuterium labelled derivative as analytical standards. Methoxetamine and normethoxetamine were used as starting materials for the preparation of O-demethylated and N-dealkylated metabolites. The multistep synthesis starts from commercially available compounds and offers good yields. Our prepared analytical standards were used for the confirmation of the suggested structure of methoxetamine metabolites in rat urine by LCMS. Capillary electrophoresis was used for the chiral separation of MXE and its metabolites using β-cyclodextrin, carboxymethylated β-cyclodextrin, and sulphated β-cyclodextrin as chiral selectors at various concentrations. Chiral separation was successful for four analytes. A mixture of MXE and its metabolites was subsequently analyzed under optimal conditions, i.e. when using 15 mmol L-1 β-cyclodextrin in 50 mmol L-1 phosphate buffer, pH 2.5. In this case, chiral separation was achieved for three analytes and all analytes were separated from each other.

BACE-2 INHIBITORY COMPOUNDS AND RELATED METHODS OF USE

Provided herein are novel compounds of Formulae I-III, and methods of using the same to selectively inhibit BACE2.

The Barbier-Grignard-Type Arylation of Ketones and Unexpected Cross-Coupling of Phenolic Ketones using Unactivated Aryl Bromides

A novel, highly versatile and efficient method has been developed for the Barbier-Grignard-type arylation of ketones and an unexpected cross-coupling of phenolic ketones was observed using unactivated bromides and magnesium in tetrahydrofuran/toluene at 96°C promoted by multicatalysts of cupric bromide (15 mol%), bismuth chloride (5 mol%) and silver bromide (10 mol%). The substituent and electronic effects on the reaction have been discussed. High yields of arylation and cross-coupling have been attained under mild conditions. A novel reasonable mechanism involving a quinone intermediate is proposed. The high chemical selectivity in the cross-coupling to the hydroxy group of phenolic ketones should help ketones find new applications.

Synthesis and application of 2,6-bis(trifluoromethyl)-4-pyridyl phosphanes: The most electron-poor aryl phosphanes with moderate bulkiness

The poor will be rich: BFPy phosphanes (see scheme) mimic the electronic and steric characters of P(C6F5)3 and PPh 3, respectively. These novel ligands showed a large ligand acceleration effect on Stille coupling, the Rh-catalyzed 1,2-addition of aryl boronic acid to unactivated ketones and the asymmetric arylation of N-tosylimine using phenylboronic acid. Copyright

Application of microreactor technology in process development

The microreactor technology is an efficient tool for kilogram-scale syntheses in continuous mode and is particularly effective for hazardous reactions that do not allow scale-up in conventional reactors. Applications to several classes of reactions including highly exothermic reactions, high-temperature reactions, reactions with unstable intermediates, and reactions involving hazardous reagents are described herein.

HYDROXYETHYLAMINE DERIVATIVES FOR THE TREATMENT OF ALZHEIMER'S DISEASE

The present invention relates to novel hydroxyethylamine compounds of formula (I): (I) having Asp2 (-secretase, BACE1 or Memapsin) inhibitory activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases characterised by elevated-amyloid levels or-amyloid deposits, particularly Alzheimer's disease.

Tramadol analogs and uses thereof

Compounds of formula I are effective in treating disorders modulated by opiate receptor activity and/or monoamine activity. In formula I, R1 is selected from alkyl, aryl, alkylaryl, substituted alkyl, substituted aryl, and substituted alkylaryl; R2 is selected from hydrogen, hydroxy, cyano, haloalkyl, glycosyl, SO2R5, and OR5; R3 and R4 are independently selected from hydrogen and lower alkyl, or R3 and R4 taken together with nitrogen form a five- or six-membered heterocyclic or substituted heterocyclic ring; and R5 is selected from alkyl, aryl, alkylaryl, substituted alkyl, substituted aryl, and substituted alkylaryl.

Organocalcium Chemistry: Preparation and Reactions of Highly Reactive Calcium

A highly reactive form of calcium was prepared by the reduction of Ca(II) salts with preformed lithium biphenylide.Remarkably, this activated calcium undergoes oxidative addition to organic bromides, chlorides, or even fluorides to form the organocalcium reagents under very mild conditions in high yields.The resulting organocalcium compounds undergo Grignard-type reactions.Transmetalation with Cu(I) salts forms calcium cuprate reagents which undergo a variety of cross-coupling reactions.The activated calcium reacts with 1,3-dienes to yield the corresponding 2-butene-1,4-diylcalcium complexes.These bis-organocalcium reagents can undergo dialkylation reactions with α,ω-alkylene dihalides and dichlorosilanes to form the corresponding 3-, 5-, and 6-membered ring derivatives.Significantly, these reactions are highly stereospecific and regioselective.

Synthesis and Anticonvulsant Activity of 1-Phenylcyclohexylamine Analogues

Thirty-eight analogues of 1-phenylcyclohexylamine (PCA), a phencyclidine (PCP) derivative, were examined for their activities in the mouse maximal electroshock (MES) seizure test and in a motor-toxicity assay.In addition, we determined the binding affinities of the compounds for PCP acceptor sites in rat brain membranes labeled with -1-piperidine.Many of the analogues were protective against MES seizures (ED50s of 4-41 mg/kg, ip) and all of these compounds caused motor toxicity.The potencies in the motor toxicity and MES seizure tests showed a moderate correlation with the affinities for PCP sites.Several analogues exhibited a greater separation of potencies in the motor toxicity and MES seizure tests than did the parent compound PCA.These were obtained by (i) 3-methylation of the cyclohexyl ring trans to the phenyl ring, (ii) methoxylation at the ortho position on the phenyl ring, and (iii) contraction of the cyclohexane ring to form the corresponding cyclopentane.