14796-31-7

Basic information

• Product Name: threo-2-(α-hydroxybenzyl)-3-coumaranone
• Synonyms: threo-2-(α-hydroxybenzyl)-3-coumaranone
• CAS NO: 14796-31-7
• Molecular Weight: 240.258
• Mol File: 14796-31-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: threo-2-(α-hydroxybenzyl)-3-coumaranone(CAS DataBase Reference)
• NIST Chemistry Reference: threo-2-(α-hydroxybenzyl)-3-coumaranone(14796-31-7)
• EPA Substance Registry System: threo-2-(α-hydroxybenzyl)-3-coumaranone(14796-31-7)

Safety Data

• Hazardous Substances Data: 14796-31-7(Hazardous Substances Data)

Upstream product

• 129878-47-3 (E)-2'-hydroxychalcone epoxide 
• 145694-66-2 2-((2S,3R)-3-Phenyl-oxiranecarbonyl)-phenol anion 
• 25518-22-3 (2-hydroxy-phenyl)-(3-phenyl-oxiranyl)-methanone 

Relevant articles and documents

Synthesis and cyclization of 1-(2-hydroxyphenyl)-2-propen-1-one epoxides: 3-Hydroxychromanones and -flavanones versus 2-(1-hydroxyalkyl)-3-coumaranones

Competitive α and β cyclization of 2'-hydroxychalcone epoxides affords 2-(α-hydroxybenzyl)-3-coumaranone and/or 3-hydroxyflavanones, which depends on the conditions employed. Epoxidation of 2'-hydroxychalcones by dimethyldioxirane followed by either base- or acid-catalyzed ring closure provides a novel, general, and efficient method for the synthesis of trans-3-hydroxyflavanones, which includes also the naturally occurring derivatives. Extension of this two-step procedure to 1-(2-hydroxyphenyl)-2-alken-1-ones was also accomplished. A strong preference for α cyclization was observed in the case of β-unsubstituted or -monoalkylated α,β-enones, while both 2,2-dimethyl-3-hydroxychromanones and 2-(1-hydroxy-1-methylethyl)-3-coumaranones were obtained from the β,β-dimethylated substrates.

Kinetics and Mechanism of the Cyclisation of Some 2'-Hydroxychalcone Epoxides and Subsequent Elimination Reactions of Aurone Hydrates

Analysis of the pH-rate profile for the cyclisation of the monoanion of 2'-hydroxychalcone epoxide which gives 3-hydroxyflavanone and of some 6'-alkoxy-substituted analogues which give mostly aurone hydrate, gives rate coefficients which quantify the preference for α over β cyclisation when 6'-substituents are present.These are considered in terms of stereoelectronic factors which may be responsible for the preference.Also reported are rate coefficients for the subsequent reaction of aurone hydrates in which aurones and coumaranones are formed.