79861-75-9

Basic information

• Product Name: 1-(3,3-Dimethyl-2-exo-bicyclo<2.2.1>heptyl)-2-bromethanon
• CAS NO: 79861-75-9
• Molecular Weight: 245.159
• Mol File: 79861-75-9.mol

Chemical Properties

• CAS DataBase Reference: 1-(3,3-Dimethyl-2-exo-bicyclo<2.2.1>heptyl)-2-bromethanon(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,3-Dimethyl-2-exo-bicyclo<2.2.1>heptyl)-2-bromethanon(79861-75-9)
• EPA Substance Registry System: 1-(3,3-Dimethyl-2-exo-bicyclo<2.2.1>heptyl)-2-bromethanon(79861-75-9)

Safety Data

• Hazardous Substances Data: 79861-75-9(Hazardous Substances Data)

Upstream product

• 15780-34-4 1-(3,3-Dimethyl-2-exo-norbornyl)-ethanone 

Relevant articles and documents

Syntheses in the Isocamphane Series, XXVI. The Synthesis of an Isocamphane-analogous Ephedrine

The synthesis of two new bicyclic phenylethylamine derivatives with potentially simpathomimetic effects is described.The synthesis of the isocamphane analogous apoephedrine (4) starts from the bicyclic methylketone 5 and leads via its α-bromoderivative 6 and the corresponding tosylamidoketone 8 to 4.The synthesis of the title compound 2 has been accomplished by preparing the α-oximinoketone 19 from the bicyclic ethylketone 15 with subsequent reduction to the amino alcohol derivative 20 and final selective monomethylation by the Johnstone procedure via the corresponding trifluoroacetamide. - Keywords: Apoephedrine analogue; Bicycloheptyl-N-methylaminoethanol derivative; Bicycloheptyl-N-methylaminopropane derivative; C-N-Bond formation; Ephedrine analogue; Isocamphane analoguous drugs; α-Oximinoketone; Simpathomimetica

Syntheses in the Isocamphane Series, XVII. Isocamphanyl-γ-butyrolactone, a New Compound with a Sandalwood Odour

The synthesis of a new compound with a sandalwood odour is described.The synthesis of the lactone 1 has been designed by molecular considerations: a bicyclus with a side chain containing 5-7 carbon atoms and an oxygene containing osmophoric group.One route to synthesize 1 leads from the ketone 3 via the Mannich base 4 to the γ-ketonitrile 6 which after hydrolysis to the γ-keto acid 7 and reduction of the latter cyclises spontaneously to 1.A shorter route starts from the α-bromoketone 13 which could be transformed by malonic ester synthesis into 7.Other synthetic routes, e.g. cyanoethylation to the homologous δ-lactone 16, aldol condensation, alkylation, carboxymethylation and carboxyethylation of 3 failed as well as the preparation of the oxazoline protected 3-bromopropionic acid for a Grignard synthesis with 3. 1 exhibits a sweed, warm odour of sandalwood with an interesting note of cedarwood. - Keywords: Cyanoethylation; γ-Keto acid; γ-Ketonitrile; γ-Lactone; Malonic ester synthesis; Mannich reaction; Oxazoline protecting group