108013-15-6

Basic information

• Product Name: 5,7-DIHYDROXY-4-PHENYL-2-CHROMANONE
• Synonyms: 5,7-DIHYDROXY-4-PHENYL-2-CHROMANONE;5,7-dihydroxy-4-phenyl-3,4-dihydro-2H-1-benzopyran-2-one
• CAS NO: 108013-15-6
• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.25
• Mol File: 108013-15-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,7-DIHYDROXY-4-PHENYL-2-CHROMANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-DIHYDROXY-4-PHENYL-2-CHROMANONE(108013-15-6)
• EPA Substance Registry System: 5,7-DIHYDROXY-4-PHENYL-2-CHROMANONE(108013-15-6)

Safety Data

• Hazardous Substances Data: 108013-15-6(Hazardous Substances Data)

Upstream product

• 4360-47-8 cinnamonitrile 
• 108-73-6 3,5-dihydroxyphenol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 5962-06-1 N-formamido-3-phenyl-2-propenamide 
• 103-26-4 methyl cinnamate 
• 102-92-1 cinnamoyl chloride 
• 621-82-9 Cinnamic acid 
• 102-92-1 Cinnamoyl chloride 
• 109853-54-5 N-cinnamoyl oxazolidin-2-one 
• 104-55-2 3-phenyl-propenal 

Relevant articles and documents

Annulation of a Highly Functionalized Diazo Building Block with Indoles under Sc(OTf)3/Rh2(OAc)4 Multicatalysis through Michael Addition/Cyclization Sequence

A highly functionalized and easily accessible six-carbon diazo building block has been developed and utilized as a 1,4-diacceptor for an efficient synthesis of functionalized tetrahydrocarbazoles, carbazoles, and tetrahydropyrido[1,2-a]indoles. The synthesis involves concurrent tandem catalysis by Sc(OTf)3 and Rh2(OAc)4. The role of Sc(OTf)3 is critical as it facilitates both the initial intermolecular Michael reaction of the indole and the subsequent Rh(II)-catalyzed intramolecular annulation. The products, tetrahydrocarbazoles and tetrahydropyridoindoles, are equipped with a β-ketoester and ester functionalities which can be utilized for further synthetic elaborations.

N-Acylation of Oxazolidinones via Aerobic Oxidative NHC Catalysis

The first N-acylation of synthetically useful oxazolidinones with aldehydes using aerobic oxidative NHC catalysis is reported. The reaction offers a broad scope of functionalized oxazolidinones in good to excellent yields. Careful choice of electron transfer mediators proved pivotal to achieve efficient aerobic N-acylation, which has previously proven difficult using NHC catalysis. The methodology allows a mild entry to acylated oxazolidinones, avoiding the use of hazardous and reactive prefunctionalized substrates.

Fast and efficient synthesis of flavanones from cinnamic acids

A fast and efficient synthesis of flavanones from cinnamic acids in three steps has been developed. First, the cinnamic acid was converted to cinnamyol chlorides using SOCl2. The acid chlorides were then treated with substituted phenols in BF3· OEt2to furnish corresponding chalcones in 42(75% yields. Base-catalyzed cyclization of the chalcones at room temperature afforded corresponding flavones in 85–95% yields. The conversion of the cinnamic acid derivatives to corresponding chalcones was found to be sensitive to the position and nature of the substituents on the aromatic rings.

An efficient synthesis of neoflavonoid antioxidants based on Montmorillonite K-10 catalysis

A new approach to synthesis of neoflavonoids, based on a high yielding Montmorillonite K-10 catalyzed lactone ring forming cyclization process, is described. The utility of this methodology is exemplified by its employment in the preparation of the substituted 4-phenylneoflavonoids 1-8. The free radical scavenging properties of these substances were evaluated. The neoflavonoids 1 and 5, which mimic esculetin-type antioxidants, were observed to quench hydrazyl free radicals.

The Michael reaction of N-cinnamoylazoles with phenols. A simple synthesis of 4-arylchroman-2-ones and 1-arylbenzo[f]chroman-3-ones

4-Arylchroman-2-ones 3 and 1-arylbenzo[f]chroman-3-ones 6 have been prepared in moderate to good yields by reaction of dihydric or trihydric phenols with p-substituted N-cinnamoylazoles in dichloromethane under reflux in the presence of DBU.

Condensation of phenols with alkylcinnamates in the presence of FeCl3

Ferric chloride catalyses the condensation of phenols with alkylcinnamates to produce 3,4-dihydro-4-arylcoumarins.

α, β-Unsaturated N-Acylureas as Useful Intermediates for the Synthesis of Indanones, Chromanones and Coumarins

α,β-Unsaturated N-acylureas, viz-N-formamido-2-butenamide (I), N-formamido-3-methyl-2-butenamide (II) and N-formamido-3-phenyl-2-propenamide (III) react with aryl alkyl ethers in the presence of PPA to afford the corresponding crotonophenones and chalcones (IV) at lower temperature and 1-indanones (V) at a higher temperature.Reactions of I and II with phenols in the presence of PPA afford the 4-chromanones (VI), while III gives 3,4-dihydro-4-phenylcoumarins (VII) in excellent yields.

THE REACTION OF MELDRUM'S ACID WITH ALDEHYDES AND PHLOROGLUCINOL: A SYNTHESIS OF DEHYDROCOUMARINS

The methylene derivatives resulting from the reaction of aldehydes with Meldrum's acid have been intercepted with phloroglucinol.The procedure offers a convenient route to certain dihydrocoumarins.