15547-89-4

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-Methoxyphenyl)cyclohexanone is used as a starting reagent for the synthesis of octahydrophenanthrene, an important intermediate in the production of morphinans. It plays a crucial role in the development of new pharmaceutical compounds with potential therapeutic applications.
Used in Organic Chemistry:
2-(3-Methoxyphenyl)cyclohexanone is also utilized in the synthesis of 2-methyl-5-phenyl morphan, a compound with potential applications in various fields of organic chemistry. Its versatility as a starting material makes it valuable for the creation of a wide range of chemical products.

Synthesis Reference(s)

The Journal of Organic Chemistry, 20, p. 1197, 1955 DOI: 10.1021/jo01126a008

InChI:InChI=1/C13H16O2/c1-15-11-6-4-5-10(9-11)12-7-2-3-8-13(12)14/h4-6,9,12H,2-3,7-8H2,1H3/t12-/m0/s1

Upstream product

• 408308-18-9 6-(3-methoxy-phenyl)-cyclohex-3-enone 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 822-87-7 2-Chlorocyclohexanone 
• 21300-30-1 lithium 1-cyclohexenolate 
• 100-66-3 methoxybenzene 
• 766-51-8 2-Chloroanisole 
• 108-94-1 cyclohexanone 
• 766-85-8 3-methoxy-1-iodobenzene 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 2398-37-0 3-methoxyphenyl bromide 
• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 286-20-4 cyclohexane-1,2-epoxide 
• 31600-88-1 m-methoxyphenyllithium 
• 2562-37-0 1-nitrocyclohexene 

Downstream Products

• 106740-45-8 [2-(3-methoxy-phenyl)-cyclohex-1-enyl]-acetic acid 
• 58559-70-9 3-[1-(3-methoxy-phenyl)-2-oxo-cyclohexyl]-propionitrile 
• 75209-39-1 morpholine enamine of 2-(m-methoxyphenyl)cyclohexanone 
• 76778-38-6 2-ethyl-2-(3-methoxyphenyl)cyclohexanone 
• 53661-21-5 2-(2-dimethylamino-ethyl)-2-(3-methoxy-phenyl)-cyclohexanone 
• 1884-40-8 6-(3-methoxyphenyl)-6-oxohexanoic acid 
• 19626-25-6 2-(3-methoxyphenyl)-2-ethoxycarbonylmethylcyclohexanone 
• 440089-99-6 7-(3,4-dimethoxyphenyl)oxepan-2-one 
• 75210-10-5 3-(9-Phenethylamino-bicyclo[3.3.1]non-1-yl)-phenol; hydrobromide 
• 75209-93-7 1-(m-methoxyphenyl)-9-phenethylaminobicyclo<3.3.1>nonane hydrochloride 
• 75210-03-6 [1-(3-Methoxy-phenyl)-bicyclo[3.3.1]non-9-yl]-methyl-phenethyl-amine; hydrochloride 
• 75209-51-7 9-amino-1-(m-methoxyphenyl)bicyclo<3.3.1>nonane 
• 767580-25-6 1-(m-methoxyphenyl)-9-(methylamino)bicyclo<3.3.1>nonane 
• 1172637-92-1 2-(3-Methoxy-phenyl)-2-propyl-cyclohexanone 

Relevant academic research and scientific papers

PREPARATION AND REACTIVITY OF λ6-VERATROLEMANGANESE TRICARBONYL TETRAFLUOROBORATE

Reaction of pentacarbonylmanganese tetrafluoroborate with veratrole (1,2-dimethoxybenzene) affords η6-veratrolemanganese tricarbonyl tetrafluoroborate in 66percent yield.This complex does not react satisfactorily with alkyllithium compounds, but it does undergo highly regioselective reaction with the lithium enolate of cyclohexanone, ortho to the MeO substituent.The product was converted to 2-(2,3-dimethoxyphenyl)cyclohexanone, thereby giving a novel and unique method for regioselective functionalization of veratrole.Similarly, anisolemanganese tricarbonyl tetrafluoroborate, and 4-bromoveratrolemanganese tricarbonyl tetrafluoroborate were prepared and their reactivity toward the enolate nucleophile was examined.

NMDA receptor antagonist and use thereof

The present invention relates to an NMDA receptor antagonist and use thereof. The NMDA receptor antagonist is a compound as shown in the formula I, and pharmaceutically acceptable salts, enantiomers, diastereoisomers, tautomers, solvates, isotope substitutes, polymorphic substances, prodrugs or metabolites thereof, and in the formula, ring A, ring B and R2 are as described in the specification. The invention also provides pharmaceutical compositions containing the compounds, and applications of the compounds in preparation of drugs for treating or preventing NMDA receptor mediated diseases.

Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl

A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.

Synthesis of Benzo[ b]furans by Intramolecular C-O Bond Formation Using Iron and Copper Catalysis

One-pot processes for the synthesis of benzo[b]furans from 1-aryl- or 1-alkylketones using nonprecious transition metal catalysts have been developed. Regioselective iron(III)-catalyzed halogenation of the aryl ring, followed by iron- or copper-catalyzed O-arylation allowed the synthesis of various structural analogues, including the benzo[b]furan-derived natural products corsifuran C, moracin F, and caleprunin B.

Diversity-Oriented Synthesis of Bioactive Azaspirocycles

A collection of novel azaspirocyclic β-arylethylamines was prepared in good yield and excellent diastereoselectivity by an expedient strategy that features condensation of a cyclic ketone with an amino allylsilane and a tandem aza-Sakurai cyclization to generate several different spirocyclic N-heterocycles. Subsequent elaboration of the spirocyclic scaffold was achieved via Pictet-Spengler cyclizations, Suzuki cross-coupling reactions, N-functionalizations, and olefin refunctionalization reactions to create a diverse library of compounds, several of which have nanomolar affinity for the sigma 1 receptor and transmembrane protein 97 (TMEM97).

Aromatic compound, preparation method and use of aromatic compound

The invention relates to an aromatic compound, a preparation method and use of the aromatic compound, andspecifically discloses a compound represented by the following formula (I), or a tautomer or anenantiomer or a diastereomer or a racemate of the compound or a mixture of the compound or a pharmaceutically acceptable salt of the compound. The invention further discloses a preparation method ofthe compound and application of the compound in treating nervous systemdiseases.

Direct Asymmetric α-Hydroxylation of Cyclic α-Branched Ketones through Enol Catalysis

Enantiopure α-hydroxy carbonyl compounds are common scaffolds in natural products and pharmaceuticals. Although indirect approaches towards their synthesis are known, direct asymmetric methodologies are scarce. Herein, we report the first direct asymmetric α-hydroxylation of α-branched ketones through enol catalysis, enabling a facile access to valuable α-keto tertiary alcohols. The transformation, characterized by the use of nitrosobenzene as the oxidant and a new chiral phosphoric acid as the catalyst, delivers a good scope and excellent enantioselectivities.

Discovery of Orally Efficacious Tetrahydrobenzimidazoles as TGR5 Agonists for Type 2 Diabetes

We have discovered a novel series of tetrahydrobenzimidazoles 3 as TGR5 agonists. Initial structure-activity relationship studies with an assay that measured cAMP levels in murine enteroendocrine cells (STC-1 cells) led to the discovery of potent agonists with submicromolar EC50 values for mTGR5. Subsequent optimization through methylation of the 7-position of the core tetrahydrobenzimidazole ring resulted in the identification of potent agonists for both mTGR5 and hTGR5 (human enteroendocrine NCI-H716 cells). While the lead compounds displayed low to moderate exposure after oral dosing, they significantly reduced blood glucose levels in C57 BL/6 mice at 30 mg/kg and induced a 13-22% reduction in the area under the blood glucose curve (AUC)0-120 min in oral glucose tolerance tests (OGTT).

Protonation of silylenol ether via excited state proton transfer catalysis

We demonstrate the photocatalytic protonation of a silylenol ether using 7-bromo-2-naphthol as an ESPT catalyst with phenol as the sacrificial proton source. Greater than 95% conversion is achieved with 1 mol% catalyst. The reaction cycle is dependent on the significantly increased acidity of the catalyst in the excited state as well as the long lifetime for the triplet excited state of 7-bromo-2-naphthol. The reaction does not occur in the absence of light (367 nm) and can readily be controlled by light intensity modulation. We also demonstrate that a 72% reaction yield can be obtained with unsubstituted naphthol as the catalyst by coupling triplet energy transfer, via a visible light absorbing (445 nm) sensitizer, into the catalytic cycle. These results open the door to an entirely new class of sensitized photocatalytic reactions that harness the excited state acidity of ESPT dyes.

Construction of a chiral quaternary carbon center by catalytic asymmetric alkylation of 2-arylcyclohexanones under phase-transfer conditions

In this paper, we present an asymmetric alkylation of modified 2-arylcyclohexanones that employs a novel chiral ammonium bromide as a phase-transfer catalyst and an achiral auxiliary as a controller to improve the enantioselectivity to afford optically enriched products having a chiral quaternary carbon center.