18458-71-4

Basic information

• Product Name: cis-2,6-diphenyltetrahydro-4H-pyran-4-one
• Synonyms: cis-2,6-diphenyltetrahydro-4H-pyran-4-one
• CAS NO: 18458-71-4
• Molecular Weight: 252.313
• Mol File: 18458-71-4.mol

Chemical Properties

• CAS DataBase Reference: cis-2,6-diphenyltetrahydro-4H-pyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: cis-2,6-diphenyltetrahydro-4H-pyran-4-one(18458-71-4)
• EPA Substance Registry System: cis-2,6-diphenyltetrahydro-4H-pyran-4-one(18458-71-4)

Safety Data

• Hazardous Substances Data: 18458-71-4(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 40989-96-6 (2S)-2-phenyl-2,3-dihydro-4H-pyran-4-one 
• 98-80-6 phenylboronic acid 
• 25830-20-0 cis-2,6-Diphenyl-4-acetoxy-1-oxacyclohexan 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 55848-87-8 t-butyl 5-hydroxy-3-oxo-5-phenylpentanoate 
• 53063-63-1 5-hydroxy-3-oxo-5-phenyl-valeric acid methyl ester 
• 74854-71-0 t-2,t-6-diphenyl-r-4-aminooxane 
• 74854-79-8 c-2,c-6-diphenyl-r-4-aminooxane 
• 25830-15-3 trans-2,6-diphenyloxan-r-4-ol 
• 65042-30-0 (2R,4s,6S)-2,6-diphenyltetrahydropyran-4-ol 
• 171969-35-0 2,6-diphenyltetrahydro-2H-pyran-4-ol 
• 542-05-2 acetonedicarboxylic acid 

Downstream Products

• 25830-15-3 2,6-Diphenyl-tetrahydro-pyran-4-ol 
• 74854-75-4 N-((2R,4R,6S)-2,6-Diphenyl-tetrahydro-pyran-4-yl)-acetamide 
• 38132-31-9 N-(2,6-diphenyltetrahydro-2H-4-pyranyl)-acetamide 
• 74854-71-0 t-2,t-6-diphenyl-r-4-aminooxane 
• 74854-79-8 c-2,c-6-diphenyl-r-4-aminooxane 
• 131042-74-5 4-Methyl-2,6-diphenyl-tetrahydro-pyran-4-ol 
• 28144-10-7 r-2,cis-6-Diphenyl-4-oxanone Oxime 
• 77743-50-1 6,8-Diphenyl-cis-2,4-diphenyl-3-oxa-7-azabicyclo<3.3.1>nonan-9-one 
• 67608-73-5 6ξ,8ξ-bis-(4-methoxy-phenyl)-2r,4c-diphenyl-3-oxa-7-aza-bicyclo[3.3.1]nonan-9-one 
• 67608-71-3 2r,4c,6ξ,8ξ-tetraphenyl-(1ξC⁹)-3-oxa-7-aza-bicyclo[3.3.1]nonan-9-one 
• 67608-72-4 6ξ,8ξ-bis-(4-chloro-phenyl)-2r,4c-diphenyl-(1ξC⁹)-3-oxa-7-aza-bicyclo[3.3.1]nonan-9-one 
• 28144-10-7 cis-2,6-diphenyl-tetrahydro-pyran-4-one oxime 
• 1227953-31-2 7,9-diphenyl-1,2,4-triaza-8-oxa-spiro(4.5)decan-3-thione 
• 1227953-28-7 C₂₄H₂₃N₃OS 

Relevant articles and documents

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Diastereoselective syntheses via Prins cyclization, crystal structures determination and theoretical studies of cis-2,6-diphenyl-4- hydroxytetrahydropyran and analogues

We report in this article the diastereoselective syntheses of tetrahydropyranyl derivatives 1-5, its cis configurational ascertainment by spectroscopy and finally the crystal structures determination that unequivocally shows the 1-5 configurations and its

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Carbonyl umpolung reactivity of enals: NHC-catalyzed synthesis of aldol products via epoxide ring opening

A novel one-pot N-heterocyclic carbene catalyzed synthesis of aldol products and their application to a facile and highly cis-selective synthesis of tetrahydropyran-4-ones is reported. The protocol involves carbonyl umpolung reactivity of enals in which the carbonyl carbon attacks nucleophilically on electrophilic terminal epoxides, regioselectively, to afford aldol adducts in good to excellent yields. Georg Thieme Verlag Stuttgart - New York.

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A one-pot, multi-component reaction for the synthesis of highly substituted tetrahydropyran-4-ones, based on the long forgotten Maitland-Japp reaction has been realised. Two different aldehydes and a derivative of a β-ketoester can be condensed regioselectively in the presence of a Lewis acid to form tetrahydropyran-4-ones in excellent yields. The diastereoselectively of the reaction was found to be dependant upon the nature of the Lewis acid and the temperature at which the reaction was carried out. This procedure was also extended to the formation of tetrahydropyran-4-ones in greater than 95% enantiomeric excess. The Royal Society of Chemistry 2005.

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Kinetics of oxidation of variously substituted epimeric pairs of 4-aminooxanes by chromium(VI) have been investigated in aqueous acetic acid in the presence of sulphuric acid.The results indicate that the oxidation is first order in and fractional order in .The reaction is acid catalysed and susceptible to solvent polarity.A mechanism involving the formation of an intermediate followed by abstraction of α-hydrogen in the rate limiting step is proposed.The reactivity of aminooxanes has been discussed on the basis of conformational and electronic effects.Activation parameters have also been determined.

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