1811-23-0

Basic information

• Product Name: Confertifolin
• Synonyms: Confertifolin;(5aS)-4,5,5a,6,7,8,9,9a-Octahydro-6,6,9aβ-trimethylnaphtho[1,2-c]furan-3(1H)-one;(5aS)-6,6,9aβ-Trimethyl-4,5,5aα,6,7,8,9,9a-octahydronaphtho[1,2-c]furan-3(1H)-one
• CAS NO: 1811-23-0
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33398
• Mol File: 1811-23-0.mol

Chemical Properties

• Boiling Point: 365.5°Cat760mmHg
• Flash Point: 152.9°C
• Appearance: /
• Density: 1.07g/cm³
• Vapor Pressure: 1.57E-05mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: Confertifolin(CAS DataBase Reference)
• NIST Chemistry Reference: Confertifolin(1811-23-0)
• EPA Substance Registry System: Confertifolin(1811-23-0)

Safety Data

• Hazardous Substances Data: 1811-23-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H22O2/c1-14(2)7-4-8-15(3)11-9-17-13(16)10(11)5-6-12(14)15/h12H,4-9H2,1-3H3/t12-,15+/m0/s1

Upstream product

• 81306-20-9 (5aS,9aS)-1,3-Dimethoxy-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan 
• 4795-87-3 (+)-winterin 
• 124313-88-8 11,12-diethoxy-11,12-epoxydrim-8-ene 
• 69748-51-2 13,14-dihydroxy-13-deisopropyldehydroabietane 
• 67119-95-3 (5S,10S)-abieta-9,11,13-trien-14-ol 
• 67919-45-3 (+)-euryfuran 
• 16776-06-0 2-Hydroxymethylen-5,5,9-trimethyl-trans-decalon 
• 60134-39-6 (-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one 
• 81306-29-8 2-(butylthiomethylene)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one 
• 81306-30-1 (5aS,9aS)-3-Butylsulfanyl-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan 
• 37866-99-2 royleanone 
• 124313-87-7 11,12-dihydrxy-11-homo-(hydroxymethyl)-drim-8-ene 
• 124313-83-3 11ξ-hydroxy-11-homo-(carboxymethyl)-drim-8-en-12,11ξ-olide 
• 81306-20-9 (5aR,9aR)-1,3-Dimethoxy-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan 

Downstream Products

• 103665-49-2 (4aS,8aS)-1,2-bis(hydroxymethyl)-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene 
• 87570-58-9 (5aS,9aS)-6,6,9a-Trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan 
• 248608-06-2 (+)-3β-hydroxyconfertifolin 
• 60134-39-6 (-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one 
• 366490-96-2 8α,9α-epoxidriman-11,12-diol 
• 58698-99-0 8αH,9αH-11,12-drimantriol 
• 364044-96-2 2,3-dehydroconfertifolin 
• 366490-98-4 12-hydroxy-(8βH)-11-nordriman-9-one 
• 364044-97-3 1α-hydroxy-2,3-dehydroconfertifolin 
• 364044-98-4 1α,11α-dihydroxy-2,3-dehydroconfertifolin 
• 366490-97-3 (8βH)-9α,11,12-drimantriol 
• 364045-02-3 1α-acetoxy-11α-hydroxy-2,3-dehydroconfertifolin 
• 364045-03-4 1α,11α-diacetoxy-2,3-dehydroconfertifolin 
• 85202-02-4 (-)-drim-7-ene-9α,11,12-triol 

Relevant articles and documents

A Regioselective Annulation of Butenolides. The Total Synthesis of (+/-) Confertifolin

γ-(Phenylsulfinyl)-α,β-unsaturated aldehydes 2, prepared from α-(n-butylthio)methylene ketones 1 via addition of lithium followed by hydrolysis and oxidation, are converted into butenolides 4 or 5 depending upon the reaction conditions.

DIISOBUTYLALUMINUM HYDRIDE REDUCTION OF UNSATURATED SYLYLCYANOHYDRINS: A NEW ENTRY TO CONFERTIFOLIN

A new entry to the drimane-related sesquiterpene Confertifolin is reported.The key step involves the conversion of a β-phenylthio-α,β-unsaturated ketone into the corresponding silylcyanohydrin followed by diisobutylaluminum hydride reduction to the homologous α,β-unsaturated aldehyde.

A NEW AND EFFICIENT ROUTE TO OPTICALLY ACTIVE DRIMANES. SYNTHESIS OF (+)-WINTERIN, (+)-CONFERTIFOLIN, (+)-ISODRIMENIN, AND (+)-BICYCLOFARNESOL

The drimane sesquiterpenes (+)-winterin, (+)-confertifolin, (+)-isodrimenin, and (+)-bicyclofarnesol were synthesised starting from royleanone, an abietane diterpenoid easily available as a main constituent of the root of some Salvia species.

A new approach to annelated butenolides. The total synthesis of (+/-)-isodrimenin

A new approach to annelated butenolides has been developed starting from trans-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-1(2H)-naphthalenone (3) and cyclohexanones.A reaction sequence consisting of formylation of the enolates of these ketones, protection of the formyl group as its dioxolane and addition of methoxy(phenylthio)methyllithium has been used to introduce the necessary functionalized carbon atoms.Rearrangement of the adduct to α-(phenylthio)aldehydes, followed by hydrolysis of the dioxolane, resulted in the formation of butenolides.The method has been demonstrated in the total synthesis of (+/-)-isodrimenin.Direct hydrolysis of the adducts, obtained after addition of methoxy(phenylthio)methyllithium, followed by treatment with acid, also gave butenolides.

Synthesis of the Drimane-related Sesquiterpenes Euryfuran, Confertifolin, and Valdiviolide

trans-3,4,4a,5,6,7,8,8a-Octahydro-5,5,8a-trimethylnaphthalene-1-(2H)-one (1) was converted into the drimane sesquiterpene euryfuran (5) in 59percent yield.Euryfuran was then used as a starting material for the synthesis two other drimane natural products, confertifolin and valdiviolide.The preparation of valdiviolide constitutes the first total synthesis of this molecule.

SYNTHESIS OF EURYFURAN, VALDIVIOLIDE, AND CONFERTIFOLIN

Starting from 5,5,9-trimethyl-trans-1-decalone (4), short and highly efficient synthesis of three drimane natural products, euryfuran (1), valdiviolide (2), and confertifolin (3) have been developed.

OZONOLYSIS OF PHENOLIC DEHYDROABIETANE DERIVATIVES. - SYNTHESES OF OPTICALLY ACTIVE (+)-CONFERTIFOLIN, (+)-VALDIVIOLIDE, (+)-WINTERIN, (+)-ISODRIMERIN, AND (+)-PALLESCENSIN A-

Ozonolysis of phenolic dehydroabietane derivatives was investigated and the products obtained by cleavage of the aromatic ring were found to be determined by the hydroxyl substitution pattern of the aromatic C-ring.Ozonolysis of the 12-hydroxy compound (ferruginol (12) gave pentanorlabdane-type compounds (14, 15, and 16).Ozonolysis of the 11-hydroxy derivative (18) and/or the 14-hydroxy derivatives (19 and 20 afforded optically active drimanic sesquiterpenes ((+)-isodrimenin (8), (+)-confertifolin (7), (+)-valdiviolide (9), and (+)-winterin (10) in one step.In this case, the mode of cleavage was different from that of 12.On the other hand, ozonolysis of the 13-hydroxy compound (3) caused cleavage in yet another manner to give the butenolide (23), which was easily converted into optically active pallescensin A (11).The mechanisms of the cleavage reactions are discussed.Keywords: - aromatic ring cleavage; ozonolysis; drimanic sesquiterpenes; phenolic diterpenes; catechol