2082-21-5

Usage

Structure

Cyclic alcohol with a seven-membered ring and a phenyl group attached to the first carbon

Usage

Synthesis of pharmaceuticals and organic chemicals

Industry Applications

Fragrance and flavor industry, perfumes, and cosmetic products

Odor

Mild, flowery, and sweet

Biological Properties

Potential as an antitumor agent

Pharmacological Properties

Inhibitor of the enzyme acetylcholinesterase, involved in Alzheimer's disease

Industrial and Medicinal Applications

Due to its unique structure and properties, it holds promise for various applications in these fields

InChI:InChI=1/C13H18O/c14-13(10-6-1-2-7-11-13)12-8-4-3-5-9-12/h3-5,8-9,14H,1-2,6-7,10-11H2

Upstream product

• 108-86-1 bromobenzene 
• 502-42-1 cycloheptanone 
• 4401-18-7 phenylcycloheptane 
• 100-58-3 phenylmagnesium bromide 
• 17257-32-8 1-propylcycloheptanol 
• 25308-75-2 1-Phenylcycloheptene 
• 3262-89-3 triphenylboroxine 
• 98-80-6 phenylboronic acid 
• 502-41-0 cycloheptanol 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 100-59-4 phenylmagnesium chloride 
• 591-51-5 phenyllithium 

Downstream Products

• 25308-75-2 1-Phenylcycloheptene 
• 59358-72-4 1,1'-Diphenyl-1,1'-bicycloheptyl 
• 17734-41-7 ω-chloroheptanoylbenzene 
• 59397-23-8 1-phenylcycloheptanamine 
• 39162-22-6 Diethyl-[2-(1-phenyl-cycloheptyloxy)-ethyl]-amine 
• 1671-75-6 Heptanophenone 
• 4401-18-7 phenylcycloheptane 
• 51348-25-5 1-phenylcycloheptyl cation 
• 39162-25-9 Diisopropyl-[2-(1-phenyl-cycloheptyloxy)-ethyl]-amine 
• 17138-96-4 S-(1-Phenyl-cycloheptyl)-L-cystein 
• 110719-01-2 7-iodo-1-phenylheptan-1-one 
• 1026791-31-0 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester 
• 1196091-20-9 (R)-3-(1-phenyl-cycloheptanecarbonyloxy)-1-(pyridazin-4-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane formate 
• 1196091-31-2 (R)-3-(1-phenyl-cycloheptanecarbonyloxy)-1-(2-pyrazin-2-yl-ethyl)-azonia-bicyclo[2.2.2]octane bromide 

Relevant academic research and scientific papers

Electrophotochemical Ring-Opening Bromination oftert-Cycloalkanols

An electrophotochemical ring-opening bromination of unstrainedtert-cycloalkanols has been developed. This electrophotochemical method enables the oxidative transformation of cycloalkanols with 5- to 7-membered rings into synthetically useful ω-bromoketones without the use of chemical oxidants or transition-metal catalysts. Alkoxy radical species would be key intermediates in the present transformation, which generate through homolysis of the O-Br bond in hypobromite intermediates under visible light irradiation.

Iodobenzene-catalyzed oxidative cleavage of olefins to carbonyl compounds

A metal-free approach for the oxidative cleavage of carbon–carbon double bonds of olefins to carbonyl compounds was established by using oxidant m-CPBA and non-metallic organocatalyst PhI in toluene/H2O. A broad scope of aromatic olefins was used. All the reactions proceeded smoothly at 35 °C in short reaction time to furnish the respective mono- and double carbonyl compounds selectively in moderate to good yields.

Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols

The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.

Azetidine derivatives and synthesis method thereof

The invention belongs to the field of chemical synthesis, and discloses an azetidine derivative and a synthesis method thereof. The structural formula of the target product azetidine derivatives is asshown in formulae (I), (II), (III), (IV) and (V). The compounds of the formulae are compounds containing an azetidine skeleton, and a nitrogen atom in the skeleton is protected by 2-picolinic acid. The target product azetidine derivatives can be: azetidinyl amide derivatives, azabicyclo[x.1.1] amide derivatives (x=3, 4, 5, 6, 7, 8, 9), azabicyclo[4.1.1] amide derivatives having a substituent at the ring, azabicyclo[4.2.0] amide derivatives and azetidine derivatives containing spirocyclic quaternary carbon. The azetidine derivatives of the present invention have certain protective effect on hydrogen peroxide-induced oxidative stress damage of HC cells.

Polycyclic Azetidines and Pyrrolidines via Palladium-Catalyzed Intramolecular Amination of Unactivated C(sp3)-H Bonds

A novel strategy to construct complex polycyclic nitrogen-containing heterocycles from aliphatic amines via picolinamide-assisted palladium-catalyzed C-H bond activation reaction was reported. The reaction exhibits broad substrate scope for the synthesis of various azabicyclic scaffolds, including azetidines and tropane-class alkaloids. Application of this method to naturally occurring (-)-cis-myrtanylamine, an unprecedented type of carbon-carbon bond activation, in which the electron-pair involved initiates an intramolecular "SN2-like" displacement of a cyclopalladium-fragment from a tertiary center, is described.

Auto de-bromine-coupling reactions of 1-aryl-7-bromocycloheptenes

Auto de-bromine-coupling reactions of 1-aryl-7-bromocycloheptenes to a new series of [7-6-6] tricyclic system were described. A variety of substituents at the para-position of the phenyl were amenable to this transformation, including electron-donating groups and halides. The presence of electron-donating groups resulted in a more efficient reaction, with higher yields than the case of halides.

Syntheses and N-methyl-D-aspartate receptor antagonist pharmacology of fluorinated arylcycloheptylamines

Selective uncompetitive antagonists of the phencyclidine (PCP) binding site of the N-methyl-D-aspartate receptor (NMDAR) are known to have therapeutic potential as anticonvulsants and neuroprotective agents. Several fluorinated molecules with each containing a cycloheptane ring were designed to probe the PCP pharmacophore and test the influence of fluorine substitution on NMDAR binding and in vivo efficacy. Syntheses and analyses of six novel compounds, 1-(4-fluorophenyl)cycloheptanamine (3), 1-(1-(4-fluorophenyl)cycloheptyl)piperidine (4), 1-(1-(4-fluorophenyl)cycloheptyl) pyrrolidine (5), 1-(3-fluorophenyl)cycloheptanamine (6), 1-(1-(3-fluorophenyl)cycloheptyl)piperidine (7), 1-(1-(3-fluorophenyl)cycloheptyl)pyrrolidine (8) and several related reference arylcyloalkylamines are described. Receptor binding was performed at the PCP site of NMDAR for each compound using [3H]-(+)-MK-801 displacement. Unexpectedly, the 3-fluoro-primary amine 6 had the greatest affinity of the series and these binding results support a different structure activity relationship (SAR) profile for arylcycloheptylamines when compared to arylcyclohexylamines like PCP. Five of the novel compounds have affinity (Ki) in the hundred nM (10-7) range. In addition, compounds 3, 5, 6, 7 and 8 were evaluated and found to exhibit neuroprotective effects from NMDA induced toxicity in vitro and compounds 6, 7 and 8 exhibited anticonvulsant activities in rats. An ED50 of 13.84 mg/kg was found for compound 6 in rat maximal electroshock (MES) test with a protective index (PI) of 3.66 against ataxia. These results support further investigation of the arylcycloheptylamine class.

The design of a novel series of muscarinic receptor antagonists leading to AZD8683, a potential inhaled treatment for COPD

A novel series of muscarinic receptor antagonists was developed, with the aim of identifying a compound with high M3 receptor potency and a reduced risk of dose-limiting side effects with potential for the treatment of COPD. Initial compound mo

Rhodium(I)/diene-catalyzed addition reactions of arylborons with ketones

Rh(I)/diene-catalyzed addition reactions of arylboroxines/arylboronic acids with unactivated ketones to form tertiary alcohols in good to excellent yields are described. By using C2-symmetric (3aR,6aR)-3,6-diaryl-1,3a,4,6a- tetrahydropentalenes as ligands, the asymmetric version of such an addition reaction, with up to 68% ee, was also realized.

QUINUCLIDINE DERIVATIVES AS MUSCARINIC M3 RECEPTOR ANTAGONISTS

The invention provides named compounds of formula (I), wherein R4 is a N-substituted quinuclidine (I) pharmaceutical compositions containing them and a process for preparing the pharmaceutical compositions. Their use in therapy for’ the treatment of conditions mediated by M3 muscarinic receptors, such as chronic obstructive pulmonary disease is also disclosed.