16750-87-1

Basic information

• Product Name: filifolone
• CAS NO: 16750-87-1
• Molecular Weight: 150.221
• Mol File: 16750-87-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: filifolone(CAS DataBase Reference)
• NIST Chemistry Reference: filifolone(16750-87-1)
• EPA Substance Registry System: filifolone(16750-87-1)

Safety Data

• Hazardous Substances Data: 16750-87-1(Hazardous Substances Data)

Upstream product

• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 164076-52-2 (E,E)-hepta-3,5-dienenitrile 
• 146607-22-9 3-hydroxy-3-methyl-hept-6-enoic acid 
• 40430-69-1 4-methylbicyclo[3.2.0]hept-3-en-6-one 
• 74-88-4 methyl iodide 
• 74994-96-0 (1S,5R)-4,7,7-Trimethyl-bicyclo[3.2.0]hept-2-en-6-one 
• 58193-39-8 8-chloro-2,6-dimethyl-octa-2,6-dien-4-one 
• 95312-02-0 6,6-(tetramethylendithio)fulven 
• 542-92-7 cyclopenta-1,3-diene 
• 95312-04-2 4-(1,3-dithiepan-2-yliden)-7,7-dimethylbicyclo<3.2.0>hept-2-en-6-on 
• 502-33-0 trans-ocimenone 
• 459-80-3 geranic acid 
• 4698-08-2 (E)-geranic acid 
• 127-09-3 sodium acetate 

Downstream Products

• 41793-01-5 4,6,6-trimethyl-1,3-cyclohexadiene-1-carboxaldehyde 
• 529-01-1 isopiperitenone 

Relevant articles and documents

Total Synthesis of the Marine Sesquiterpenoid Raikovenal through a Novel Utilization of the Bicycloheptenone Approach

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TOTAL SYNTHESIS OF (+-)-FILIFOLONE

Monoterpene filifolone has been synthesized by an intramolecular acid catalyzed alkylation of dienic diazoketone.The potential utility of the key transformation in the synthesis of a new terpene synthon is indicated.

Synthesis of Methyl Substituted Bicyclohept-3-en-6-ones and 3,3a,4,6a-Tetrahydro-2H-cyclopentafuran-2-ones.

Treatment of methyl mono- or bisubstituted 3-hydroxy-6-alkenoic acids in acetic anhydride and potassium acetate give the corresponding bicyclohept-3-en-6-ones in fair to good yields.This reaction appears to be of general applicability to prepare the methyl derivatives in all the positions of the five membered ring.The synthesis of 4,7,7-trimethylbicyclohept-3-en-6-one (filifolone) by an efficient bicyclization of 3-hydroxy-3-methyl-6-heptenoic acid followed by the geminal dimethylation of the intermediate 4-methylbicyclohept-3-en-6-one is reported.The latter reaction proved to be a general method when performed on bicyclohept-3-en-6-ones and on bicyclohept-2-en-6-one. 3,3a,4,6a-Tetrahydro-2H-cyclopentafuran-2-ones, important starting materials in the synthesis of linear condensed triquinane sesquiterpenes, have been prepared in an efficient manner by the easy bicyclization of 3-hydroxy-6-heptenoic acids, followed by a Baeyer-Villiger oxidation of the bicyclohept-3-en-6-one intermediates.

Addition of dimethylketene to 6-heterosubstituted fulvenes. Synthesis of (±)-filifolone

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