60426-81-5

Basic information

• Product Name: (3aS,4aR,7aR,8R,9aS)-4a,8-dimethyl-3-methylidenedecahydroazuleno[6,5-b]furan-2,5-dione
• CAS NO: 60426-81-5
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.3175
• Mol File: 60426-81-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 407.3°C at 760 mmHg
• Flash Point: 181.4°C
• Density: 1.13g/cm³
• Vapor Pressure: 7.61E-07mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: (3aS,4aR,7aR,8R,9aS)-4a,8-dimethyl-3-methylidenedecahydroazuleno[6,5-b]furan-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,4aR,7aR,8R,9aS)-4a,8-dimethyl-3-methylidenedecahydroazuleno[6,5-b]furan-2,5-dione(60426-81-5)
• EPA Substance Registry System: (3aS,4aR,7aR,8R,9aS)-4a,8-dimethyl-3-methylidenedecahydroazuleno[6,5-b]furan-2,5-dione(60426-81-5)

Safety Data

• Hazardous Substances Data: 60426-81-5(Hazardous Substances Data)

Upstream product

• 60403-31-8 (3aS,4aR,5R,7aR,8S,9aR)-5-tert-Butoxy-4a,8-dimethyl-3-methylene-decahydro-azuleno[6,5-b]furan-2-one 
• 123130-59-6 3-(1-methylethenyl)-2-<2-<(trimethylsilyl)methyl>allyl>-2-cyclopenten-1-one 
• 146644-12-4 (+/-)-4-methyl-7-methylene-3,4,5,6,7,8-hexahydroazulen-1(2H)-one 
• 146644-15-7 (+/-)-4-methyl-1,2,3,4,5,8-hexahydro-1-oxoazulene-7-ethanol 
• 74615-16-0 (1R,3aR,4S,6R,7S,8aR)-1-tert-Butoxy-7-(2-hydroxy-ethyl)-4,8a-dimethyl-decahydro-azulen-6-ol 
• 114506-14-8 (<1SR,3aSR,4SR,7SR,8aSR>-1-(t-Butyldimethylsiloxy)-4,8a-dimethyloctahydro-6(1H)-azulenon-7-yl)essigsaeure ethylester 
• 114506-15-9 [(3S,3aS,5S,8S,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-3a,8-dimethyl-6-oxo-decahydro-azulen-5-yl]-acetic acid 
• 72341-88-9 (3aS,4aR,5R,7aR,8R,9aS)-5-Hydroxy-4a,8-dimethyl-2-oxo-dodecahydro-azuleno[6,5-b]furan-3-carboxylic acid 
• 105787-84-6 3-(<1SR,2SR,5SR>-2-(t-Butyldimethylsiloxy)-5-isopropenyl-1-methylcyclopentyl)propionitril 
• 105787-85-7 3-(<1SR,2SR,5SR>-2-(t-Butyldimethylsiloxy)-5-isopropenyl-1-methylcyclopentyl)propionaldehyd 
• 105787-87-9 <1SR,3aSR,6SR,8aSR>-1-(t-Butyldimethylsiloxy)-8a-methyl-4-methylen-decahydro-6-azulenol 
• 105787-86-8 <1SR,6RS,8aSR>-1-(t-Butyldimethylsiloxy)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-6-azulenol 
• 105787-86-8 <1SR,6SR,8aSR>-1-(t-Butyldimethylsiloxy)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-6-azulenol 
• 105787-83-5 3-((1S,5S)-2-Hydroxy-5-isopropenyl-1-methyl-cyclopentyl)-propionitrile 

Downstream Products

• 5945-42-6 (+/-)-aromaticin 

Relevant articles and documents

Allylsilane-Based Annulations. Direct Stereoselective Syntheses of (+/-)-Graveolide and (+/-)-Aromaticin

An allylsilane-based annulation was used to construct a functionalized perhydroazulene.The C(1), C(5), and C(10) stereocenters, characteristic of the helenanolides, were established using a reductive alkylation strategy.Stereoselective syntheses of the pseudoguaianolides graveolide and aromaticin were achieved.

An Annulation Approach to the Synthesis of Pseudoguaianolide Sequiterpene Lactones. Total Syntheses of dl-Confertin and dl-Aromatin

Annulation of 2-methyl-1,3-cyclopentanedione with 4-(halomethyl)-5-(1-oxopropyl)-3-furancarboxylic esters 6a or 6b provides the fully assembled tricyclic framework, 1, of the cytotoxic pseudoguaianolide sequiterpene lactones.Dienedione 1 has been used to construct (+/-)-confertin (2) and (+/-)-aromatin (3).Experiments relevant to a total synthesis of the more complex helenanolides (e.g., the fastigilins, 4) also are discussed.

Total Synthesis of Pseudoguaianolides: (+/-)-Aromaticin and (+/-)-Aromatin

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