81052-99-5

Basic information

• Product Name: 4-(4-Methyl-3-penten-1-ynyl)furan-2(5H)-one
• Synonyms: 4-(4-Methyl-3-penten-1-ynyl)furan-2(5H)-one;Cleviolide
• CAS NO: 81052-99-5
• Molecular Weight: 0
• Mol File: 81052-99-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(4-Methyl-3-penten-1-ynyl)furan-2(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Methyl-3-penten-1-ynyl)furan-2(5H)-one(81052-99-5)
• EPA Substance Registry System: 4-(4-Methyl-3-penten-1-ynyl)furan-2(5H)-one(81052-99-5)

Safety Data

• Hazardous Substances Data: 81052-99-5(Hazardous Substances Data)

Upstream product

• 64305-70-0 1,1-dibromo-4-methyl-1,3-pentadiene 
• 565-68-4 4-methylpent-1-yn-3-ol 
• 56634-50-5 4-bromo-5H-furan-2-one 
• 62338-12-9 trimethyl(4-methylpent-3-en-1-yn-1-yl)silane 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 145439-09-4 4-(tributylstannyl)-2,5-dihydrofuran-2-one 
• 151722-94-0 1-Iodo-4-methylpent-3-en-1-yne 
• 1595-53-5 4-methylpent-3-en-1-yne 
• 31555-04-1 ethyl 4-hydroxy-2-butynoate 

Downstream Products

• 81053-16-9 (E)-Scobinolide 
• 81053-17-0 (Z)-Scobinolide 

Relevant articles and documents

Directing tandem catalyzed reactions as an approach to furans and butenolides

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A concise and efficient novel synthesis of cleviolide

Cleviolide I has been synthesized in 73 % overall yield by a short reaction sequence involving the preparation of 4-methyl-1-trimethylsilylpent- 3-en-1-yne 7 from trimethylsilylethynylzinc chloride 6 and 1-bromo-2- methylpropene 5, the direct conversion of 7 into the corresponding 1- tributylstannyl derivative 8 and the Pd-catalysed reaction of this organotin derivative with 4-bromofuran-2(5H)-one 10.

Synthesis of cleviolide and the scobinolides

The palladium-catalysed cross-coupling reaction of 4-tributylstannylfuran-2(5H)-one 3 with 1-iodo-4-methylpent-3-en-1-yne 4a gives the natural product cleviolide; from this substance may be prepared both (Z)- and (E)-isomers of scobinolide.