22562-09-0

Basic information

• Product Name: 5-Methoxy-8,8-dimethyl-6-(2-methyl-1-oxo-2-butenyl)-4-phenyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one
• Synonyms: 5-Methoxy-8,8-dimethyl-6-(2-methyl-1-oxo-2-butenyl)-4-phenyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one;Apetalolide
• CAS NO: 22562-09-0
• Molecular Formula: C₂₆H₂₄O₅
• Molecular Weight: 416.46576
• Mol File: 22562-09-0.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Methoxy-8,8-dimethyl-6-(2-methyl-1-oxo-2-butenyl)-4-phenyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methoxy-8,8-dimethyl-6-(2-methyl-1-oxo-2-butenyl)-4-phenyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one(22562-09-0)
• EPA Substance Registry System: 5-Methoxy-8,8-dimethyl-6-(2-methyl-1-oxo-2-butenyl)-4-phenyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one(22562-09-0)

Safety Data

• Hazardous Substances Data: 22562-09-0(Hazardous Substances Data)

Upstream product

• 31525-67-4 dimethylacetal of 3-methyl-3-hydroxybutyraldehyde 
• 161633-73-4 5-Methoxy-8,8-dimethyl-6-(2-methylbutanoyl)-4-phenyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one 
• 98192-58-6 5,7-Dihydroxy-6-(2-methylbutanoyl)-4-phenyl-2H-chromen-2-one 
• 30390-18-2 5-Hydroxy-8,8-dimethyl-6-(2-methylbutanoyl)-4-phenyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one 
• 172805-16-2 6-(2-Bromo-2-methylbutanoyl)-5-methoxy-8,8-dimethyl-4-phenyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-8-one 

Relevant articles and documents

Synthesis of the Calophyllum coumarins. Part 2

Synthetic routes leading to the synthesis of the natural 4-phenyl, 4-propyl and 4-methyl coumarins isolated from Calophyllum sp. are presented. 4-Aryl or -alkyl, 8- and 6-acyl 5,7-dihydroxy coumarins were chromenylated and then methylated at the 5 or 7 positions.A 4-step hydrobromination-bromination-double dehydrobromination sequence converted the 2-methylbutanoyl side chain into the (E)-2-methylbut-2-enoyl (tigloyl) group to give calophyllolide, oblongulide, their natural 4-propyl analogue and the corresponding regioisomers.Demethylation and cyclisation of the tigloyl group gave inophyllums C and E, tomentolides A and B, and calanolide D.Sodium boranuide reduction of the 2,3-dimethylchromanone ring afforded inophyllums A, B, D and P, soulattrolide, calanolides A-C, costatolide, and cordatolides A and B.The structures of calanolides C and D, oblongulide and apetatolide have been reassigned.The previously unknown stereochemistry about the 2,3-dimethylchromanone ring of tomentolides A and B has been established as trans.