18367-70-9

Basic information

• Product Name: [(1S,3aR,4S,8aS)-4,8,8-trimethyldecahydro-1,4-methanoazulen-9-yl]methyl acetate
• CAS NO: 18367-70-9
• Molecular Formula: C₁₇H₂₈O₂
• Molecular Weight: 264.403
• EINECS: 242-240-0
• Mol File: 18367-70-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 302.4°C at 760 mmHg
• Flash Point: 136.3°C
• Density: 0.986g/cm³
• Vapor Pressure: 0.000991mmHg at 25°C
• Refractive Index: 1.482
• CAS DataBase Reference: [(1S,3aR,4S,8aS)-4,8,8-trimethyldecahydro-1,4-methanoazulen-9-yl]methyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: [(1S,3aR,4S,8aS)-4,8,8-trimethyldecahydro-1,4-methanoazulen-9-yl]methyl acetate(18367-70-9)
• EPA Substance Registry System: [(1S,3aR,4S,8aS)-4,8,8-trimethyldecahydro-1,4-methanoazulen-9-yl]methyl acetate(18367-70-9)

Safety Data

• Hazardous Substances Data: 18367-70-9(Hazardous Substances Data)

Usage

General Description

The chemical compound "[(1S,3aR,4S,8aS)-4,8,8-trimethyldecahydro-1,4-methanoazulen-9-yl]methyl acetate" is a complex organic molecule with a unique structure. It consists of a methyl acetate group attached to a 1,4-methanoazulen-9-yl moiety, which is a bicyclic hydrocarbon. The molecule has a total of 16 carbon atoms and 26 hydrogen atoms, and its molecular formula is C15H26O2. [(1S,3aR,4S,8aS)-4,8,8-trimethyldecahydro-1,4-methanoazulen-9-yl]methyl acetate is likely to possess interesting chemical and pharmacological properties, and its structure suggests that it may have potential applications in the fields of organic synthesis, pharmaceuticals, and materials science. Further research and analysis are needed to fully understand the properties and potential uses of this compound.

Upstream product

• 126899-53-4 Acetic acid (1R,3aS,4S,6R,7R,9R)-6-hydroxy-7-methoxy-4,8,8-trimethyl-decahydro-1,4-methano-azulen-9-ylmethyl ester 
• 126899-54-5 Acetic acid (1R,3aS,4S,7S,9R)-7-methoxy-4,8,8-trimethyl-decahydro-1,4-methano-azulen-9-ylmethyl ester 
• 126899-57-8 Acetic acid (1R,3aS,4S,6R,7R,9R)-7-methoxy-4,8,8-trimethyl-6-phenoxythiocarbonyloxy-decahydro-1,4-methano-azulen-9-ylmethyl ester 

Downstream Products

• 475-20-7 longifolene 

Relevant articles and documents

Cycloaddition Routes to Tricyclo1,7.02,9>undecanes: A Direct Total Synthesis of (+)-Longifolene via an Intramolecular Diels-Alder Strategy

The total synthesis of the sesquiterpene (+)-longifolene (1) by an intramolecular Diels-Alder cycloaddition strategy is described.Addition of methyllithium to the epoxyfulvene 13, derived from cyclopentadiene and 3,4-epoxy-2-butanone, led to an exo-tet cyclization of the resulting cyclopentadienyl anion to generate the spirohepta-4,6-diene alcohol 14.Resolution of this material was effected via its menthyl carbonate derivative 15.Oxidation of the (+)-R-alcohol with active MnO2 afforded the cyclopropyl aldehyde 16 which was condensed with the anion derived from methyl 3-methylcrotonate in the presence of cadmium chloride to gen erate the unsaturated lactone 20 or the unsaturated ester 18.Microwave heating of the silyl triene 19 effected cycloaddition to the adduct 21.Hydrogenolysis of the alcohol 22 afforded the "sinularene" skeleton 25.Cyclopropane ring cleavage of the derived ketones 23, 30, and the thiocarbonate 27 was examined but only in the Li/NH3 reduction of 30 was the longifolene skeleton 33 produced as a significant product which unfortunately could not be separated from its isomer 32.Consequently the successful route utilized regiospecific cleavage of the cyclopropane ring in the cyclopentadiene 20 in methanol catalyzed by BF3*Et2O to afford the substituted cyclopentadiene lactone(s) 34 (83percent).Cyclization proceeded smoothly, in a sealed tube, in toluene, in a microwave oven to afford the single tetracyclic adduct 39 in 97percent yield.Double bond hydrogenation and reduction of the lactone with LiAlH4 afforded the substituted longifolene skeleton, and the resulting primary alcohol was acetylated selectively to give 40.Free-radical-mediated replacement of the secondary oxygen functions was accomplished via the phenoxythiocarbonate derivative to afford the methoxy acetate 43.Alternatively the reaction sequence could b e modified to convert 39 to 41 to 42 and then to 43.Methoxy cleavage (Me3SiI) and a second free-radical reaction gave the acetate 44.Pyrolysis of this acetate (525 deg C) provided (+)-longifolene (1).