37087-68-6

Basic information

• Product Name: 2-(4-METHOXYPHENYL)-1-CYCLOHEXANONE
• Synonyms: 2-(4-METHOXYPHENYL)-1-CYCLOHEXANONE
• CAS NO: 37087-68-6
• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.26
• Mol File: 37087-68-6.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 335.7°Cat760mmHg
• Flash Point: 149.9°C
• Appearance: /
• Density: 1.068g/cm³
• Vapor Pressure: 0.000118mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: 2-(4-METHOXYPHENYL)-1-CYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-METHOXYPHENYL)-1-CYCLOHEXANONE(37087-68-6)
• EPA Substance Registry System: 2-(4-METHOXYPHENYL)-1-CYCLOHEXANONE(37087-68-6)

Safety Data

• Hazardous Substances Data: 37087-68-6(Hazardous Substances Data)

Usage

Description

2-(4-METHOXYPHENYL)-1-CYCLOHEXANONE is an organic compound that serves as a valuable synthetic intermediate in the pharmaceutical industry. It is characterized by its unique molecular structure, which features a cyclohexanone ring with a 4-methoxyphenyl group attached to the 2nd carbon. This structure endows it with specific chemical properties that make it a versatile building block for the development of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
2-(4-METHOXYPHENYL)-1-CYCLOHEXANONE is used as a synthetic intermediate for the development of rac-14-epi-Dextromethorphan (D299440), an analog of Dextromethorphan (D299445). Dextromethorphan is a well-known antitussive compound that also exhibits analgesic properties, making it a common ingredient in cough medication formulations. The synthesis of rac-14-epi-Dextromethorphan through the use of 2-(4-METHOXYPHENYL)-1-CYCLOHEXANONE allows for the exploration of new therapeutic options and potential improvements in the treatment of cough and pain.

InChI:InChI=1/C13H16O2/c1-15-11-8-6-10(7-9-11)12-4-2-3-5-13(12)14/h6-9,12H,2-5H2,1H3

Upstream product

• 93-59-4 Perbenzoic acid 
• 20758-60-5 1-(4-methoxyphenyl)cyclohexene 
• 854727-09-6 6-(4-methoxy-phenyl)-cyclohex-3-enone 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 822-87-7 2-Chlorocyclohexanone 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 18649-43-9 4-methoxyphenyllead(IV) triacetate 
• 20859-19-2 (+/-)-trans-2-(4-methoxyphenyl)cyclohexanol 
• 2562-37-0 1-nitrocyclohexene 
• 100-66-3 methoxybenzene 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 823-45-0 2-(hydroxymethylene)cyclohexanone 
• 67-56-1 methanol 
• 89008-80-0 2-(4-Methoxy-phenyl)-cyclohexan-1-ol 

Downstream Products

• 102010-21-9 2-(4-Methoxy-phenyl)-1-[2]pyridylmethyl-cyclohexanol 
• 108062-64-2 2-(4-methoxyphenyl)cycloheptan-1-one 
• 613-36-5 4-cyclohexylanisole 
• 20859-19-2 (+/-)-trans-2-(4-methoxyphenyl)cyclohexanol 
• 79664-42-9 2-(4-Methoxy-phenyl)-1-p-tolyl-cyclohexanol 
• 89008-80-0 2-(4-Methoxy-phenyl)-cyclohexan-1-ol 
• 52839-57-3 (2R,3R,4R)-4-(4-Methoxy-phenyl)-1-oxa-spiro[2.5]octane-2-carbonitrile 
• 52839-58-4 (2S,3R,4R)-4-(4-Methoxy-phenyl)-1-oxa-spiro[2.5]octane-2-carboxylic acid methyl ester 
• 84839-21-4 2-(4-Methoxy-phenyl)-2-methyl-cyclohexan-1-on 
• 5537-76-8 6-(4-methoxyphenyl)-6-oxohexanoic acid 
• 20859-19-2 (+/-)-cis-2-(4-Methoxy-phenyl)-cyclohexanol 
• 190256-71-4 (R)-2-(4-methoxyphenyl)cyclohexan-1-one 
• 15638-15-0 1,2-bis(p-methoxyphenyl)cyclohexene 

Relevant articles and documents

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.

I(III)-catalyzed oxidative cyclization - Migration tandem reactions of unactivated anilines

An I(III)-catalyzed oxidative cyclization-migration tandem reaction using Selectfluor as the oxidant was developed that converts unactivated anilines into 3H-indoles is reported herein. The reaction requires as little as 1 mol % of the iodocatalyst and is mild, tolerating pyridine and thiophene functional groups, and the dependence of the diastereoselectivity of the process on the identity of the iodoarene or iodoalkane precatalyst suggests that the catalyst is present for the stereochemical determining C-N bond forming step.

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.