16479-72-4

Basic information

• Product Name: 3,5-Methano-2H-cyclopenta[b]furan-2-one, hexahydro-6-hydroxy-, (3R,3aS,5R,6R,6aR)-rel-
• CAS NO: 16479-72-4
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• Mol File: 16479-72-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3,5-Methano-2H-cyclopenta[b]furan-2-one, hexahydro-6-hydroxy-, (3R,3aS,5R,6R,6aR)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Methano-2H-cyclopenta[b]furan-2-one, hexahydro-6-hydroxy-, (3R,3aS,5R,6R,6aR)-rel-(16479-72-4)
• EPA Substance Registry System: 3,5-Methano-2H-cyclopenta[b]furan-2-one, hexahydro-6-hydroxy-, (3R,3aS,5R,6R,6aR)-rel-(16479-72-4)

Safety Data

• Hazardous Substances Data: 16479-72-4(Hazardous Substances Data)

Upstream product

• 68763-55-3 dioxa-3,5 exo phenyl-4 syn carbomethoxy-9 endo tricyclo <5.2.1.0^2,6> decane 
• 117835-14-0 bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride 
• 77299-91-3 Benzoic acid (1S,2S,3S,6S,7R)-5-oxo-4-oxa-tricyclo[4.2.1.0^3,7]non-2-yl ester 
• 2903-75-5 (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 
• 120-74-1 endo-norbornenecarboxylic acid 

Relevant articles and documents

Amides containing two norbornene fragments. Synthesis and chemical transformations

Reactions of stereochemically pure bicyclo[2.2.1]hept-5-en-exo- and endo-2-ylmethylamines with bicyclo[2.2.1]hept-2-ene-5-carbonyl chlorides gave the corresponding carboxamides having two norbornene fragments. Their conformations and steric strains were studied by the MM2 molecular mechanics method, and electron density distribution in their molecules was determined by PM3 quantum-chemical calculations. The results of calculation of the energy of activation for epoxidation of the dienes in the gas phase and in solution (COSMO) showed that chemoselective oxidation of only one double bond therein is impossible. The corresponding diepoxy derivatives were synthesized by oxidation of the dienes with peroxyacetic acid; the oxidation of amides with endo orientation of the carbonyl group was accompanied by heterocyclization with formation of exo-2-hydroxy-4-oxatricyclo[4.2.1.03,7]nonan-5-one. Reduction of the amides and their epoxy derivatives with lithium tetrahydridoaluminate afforded the corresponding secondary amines possessing two cage-like fragments; the reduction products were functionalized at the nitrogen atom by treatment with p-nitrobenzenesulfonyl chloride and p-toluenesulfonyl isocyanate. The structure of the prepared compounds was confirmed by the IR and 1H and 13C NMR spectra.

ACTION DU N-BROMOSUCCINIMIDE SUR LES DIOXOLANNES EN SERIE BICYCLOHEPTANIQUE. LIMITATION DES TRANSPOSITIONS DE WAGNER-MEERWEIN

Vicinal benzoyloxy-trans-bicycloheptanic bromhydrins, otherwise difficult to obtain are formed from N-bromosuccinimide and norbornanes bearing a 2-aryl-1,3 dioxolane skeleton.The greater stability of the intermediate dioxolenium ion reduces the tendency towards both Wagner-Meerwein rearrangement and neighbouring group participation by chlorine, processes usually observed when a less stable intermediate is involved.Nevertheless, methoxycarbonyl neighbouring group participation and Wagner-Meerwein rearrangement occur in methoxycarbonylbicycloheptane and in a bornanic compound respectively.