29507-75-3

Basic information

• Product Name: 5-Hydroxy-2,2,8-trimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one
• Synonyms: 5-Hydroxy-2,2,8-trimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one;Spatheliachromene
• CAS NO: 29507-75-3
• Molecular Formula: C15H14O4
• Molecular Weight: 258.26926
• Mol File: 29507-75-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Hydroxy-2,2,8-trimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxy-2,2,8-trimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one(29507-75-3)
• EPA Substance Registry System: 5-Hydroxy-2,2,8-trimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one(29507-75-3)

Safety Data

• Hazardous Substances Data: 29507-75-3(Hazardous Substances Data)

Upstream product

• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 1013-69-0 eugenin 
• 578-72-3 5,7-dihydroxy-2-methyl-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one 
• 83805-66-7 7-(1,1-dimethyl-2-propynyloxy)-8-iodo-5-methoxy-2-methyl-4H-1-benzopyran-4-one 
• 24128-11-8 6-Acetyl-5,7-dihydroxy-3,4-dihydro-2,2-dimethyl-2H-<1>benzopyran 
• 83805-61-2 1-(4-benzyloxy-2-hydroxy-6-methoxyphenyl)-1,3-butanedione 
• 83805-64-5 7-hydroxy-8-iodo-5-methoxy-2-methyl-4H-1-benzopyran-4-one 
• 83805-62-3 7-benzyloxy-5-methoxy-2-methyl-4H-1-benzopyran-4-one 
• 39548-89-5 1-(4-(benzyloxy)-2-hydroxy-6-methoxyphenyl)ethan-1-one 
• 3449-40-9 7-hydroxy-5-methoxy-2-methylchromone 
• 13475-11-1 Isopeucenin 
• 4670-29-5 5-Hydroxy-2,8,8-trimethyl-8H-pyrano<2,3-h>chromone 
• 31273-62-8 7-(1,1-dimethyl-prop-2-ynyloxy)-5-hydroxy-2-methyl-chromen-4-one 

Downstream Products

• 33845-34-0 10-(3,3-dimethylallyl)spatheliachromene 

Relevant articles and documents

Studies in Pyranomethylchromones and Prenylated Pyranomethylchromones

5,7-Dihydroxy-2-methylchromone (I) on prenylation with 2-methyl-3-buten-2-ol in the presence of BF3 etherate yields pulverin (II) and peucenin (III), which are separable by column chromatography.Cyclodehydrogenation of II with DDQ in benzene under reflux for 6 hr affords 6-(3,3-dimethylallyl)alloptaeroxylin (IV) and 10-(3,3-dimethylallyl)spatheliachromene (V) while prolonged refluxing (70 hr) yields in addition to IV and V, the bispyranochromone (VI) identified as spatheliabischromene.Pyranochromones IV, V and VI have also been synthesised by alternative routes.Alloptaeroxylin (VII) on prenylation with 2-methyl-3-buten-2-ol in the pres ence of BF3 etherate gives IV.Compound III undergoes cyclodehydrogenation with DDQ to give spatheliachromene (VIII) which on prenylation affords V.Acid-catalysed cyclisation of IV followed by NBS/DDQ dehydrogenation of the resultant dihydrodipyranochromone (IX) furnishes VI.

A Convenient Synthesis of Linear 2-Methylpyranochromones

A convenient synthesis of linear 2-methylpyranochromones, viz., spatheliachromen(5-hydroxy-2,2,8-trimethyl-2H,6H-benzodipyran-6-one), O-methylspatheliachromen (5-methoxy-2,2,8-trimethyl-2H,6H-benzodipyran-6-one) (8) and O-methylallopteroxylin (5-methoxy-2,8,8-trimethyl-4H,8H-benzodipyran-4-one> is described by blocking the eighth position of the corresponding 7-propargyl ether derivative 7-(1,1-dimethyl-2-propynyloxy)-8-iodo-5-methoxy-2-methyl-4H-1-benzopyran-4-one with iodine followed by thermal cyclization.The linear pyranochromones 2,2,8-trimethyl-2H,6H-benzodipyran-6-one and 8 are also synthesized starting with the easily available appropriate 3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-7-ols following the steps of Claisen condensation with ethyl acetate, cyclization with ethanolic sulfuric acid followed by dehydrogenation with NBS.