731-75-9

Basic information

• Product Name: Alloxanthoxyletin
• Synonyms: Alloxanthoxyletin;2,2-Dimethyl-5-methoxy-2H,8H-benzo[1,2-b:3,4-b']dipyran-8-one;5-Methoxy-2,2-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-8-one;Alloxanthyletin
• CAS NO: 731-75-9
• Molecular Formula: C15H14O4
• Molecular Weight: 258.26926
• Mol File: 731-75-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Alloxanthoxyletin(CAS DataBase Reference)
• NIST Chemistry Reference: Alloxanthoxyletin(731-75-9)
• EPA Substance Registry System: Alloxanthoxyletin(731-75-9)

Safety Data

• Hazardous Substances Data: 731-75-9(Hazardous Substances Data)

Upstream product

• 521097-44-9 3,4-dihydroalloxanthoxyletin 
• 130364-30-6 7-hydroxy-5',5a'-dimethylpyrano[2',3'-f]-(2H)-chromen-2-one 
• 74-88-4 methyl iodide 
• 7661-00-9 5-methoxy-2,2-dimethyl-7-(toluene-4-sulfonyloxy)-chroman-4-one 
• 108-73-6 3,5-dihydroxyphenol 
• 29373-14-6 2,2-dimethylchromane-5,7-diol 
• 883-09-0 5,7-dihydroxy-2,2-dimethylchroman-4-one 
• 50386-17-9 3,4-Dihydro-7-hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran 
• 541-47-9 3-Methylbutenoic acid 
• 54416-00-1 toluene-4-sulfonic acid 5-methoxy-2,2-dimethyl-chroman-7-yl ester 
• 676529-26-3 toluene-4-sulfonic acid 5-hydroxy-2,2-dimethyl-4-oxo-chroman-7-yl ester 
• 16348-68-8 5-methoxy-2,2-dimethyl-2,3-dihydro-pyrano[2,3-f]chromene-4,8-dione 
• 1191-16-8 3-methylbut-2-enyl acetate 

Relevant articles and documents

A catalyst-free one-pot construction of skeletons of 5-methoxyseselin and alloxanthoxyletin in water

In refluxing water and without an additional catalyst, electron-rich phenols could react with alkynoic acids or alkynoates to provide coumarin structures. The skeletons of two natural pyranocoumarins, 5-methoxyseselin and alloxanthoxyletin, could be constructed (total yield up to 76%) in an aqueous multicomponent reaction in which isoprenyl acetate, propiolic acid, and phloroglucinol were simply mixed and refluxed in water.

Atom economy. Palladium-catalyzed formation of coumarins by addition of phenols and alkynoates via a net C-H insertion

A strategy to achieve ortho substitution of phenols initiated by an ortho-palladation to create coumarins was examined. Indeed, treatment of alkynoates with electron-rich phenols in the presence of a palladium catalyst and an acid does generate coumarins. The scope of the reaction with respect to the phenol and the alkynoates is defined. With unsymmetrical aromatic substrates, generally good regioselectivity that reflects the HOMO coefficients can be observed. In the course of these studies, numerous important naturally occurring coumarins have been synthesized, including fraxinol methyl ether, ayapin, herniarin, xanthoxyletin, and alloxanthoxyletin. The fact that a Pd(0) is the precatalyst rather than a Pd(+2) species and that an acid that reduces Pd(+2) salts, formic acid, functions better than other carboxylic acids raises doubts about the initial working hypothesis. A novel mechanism involving a palladium phenoxide formed from a hydridopalladium carboxylate and phenol is invoked to rationalize the results.