84694-53-1

Basic information

• Product Name: 8,9-trans-6-<2-(dimethylamino)-1(R)-phenylethoxy>octahydrophenanthrene
• CAS NO: 84694-53-1
• Molecular Weight: 349.516
• Mol File: 84694-53-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 8,9-trans-6-<2-(dimethylamino)-1(R)-phenylethoxy>octahydrophenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: 8,9-trans-6-<2-(dimethylamino)-1(R)-phenylethoxy>octahydrophenanthrene(84694-53-1)
• EPA Substance Registry System: 8,9-trans-6-<2-(dimethylamino)-1(R)-phenylethoxy>octahydrophenanthrene(84694-53-1)

Safety Data

• Hazardous Substances Data: 84694-53-1(Hazardous Substances Data)

Upstream product

• 84694-35-9 2-phenyl>-3,3-dimethyl-5(R)-phenyloxazolidinium iodide 

Downstream Products

• 16804-85-6 8,9-trans-hexahydrophenanthrene 
• 16306-39-1 trans-octahydrophenanthrene 

Relevant articles and documents

A New Approach to Asymmetric Synthesis of Polycycles on the Basis of o-Quinodimethane Generation

The fluoride anion induced 1,4-elimination of 2-phenyl>-3,3-dimethyloxazolidinium salts generates (E,E)-α-alkyl-α'--o-quinodimethane intermediates, which are trapped stereoselectively with dienophiles to give polycycles.Intramolecular cyclization of 2-phenyl>-3,3-dimethyl-4-(R)-methyl-5(R)-phenyloxazolidinium triflate at 0 deg C produces a 3:1 diastereoisomeric mixture of 6--trans-octahydrophenanthrene, which is converted by hydrogenolysis on Pd/C to trans-octahydrophenanthrene with D +46.6 deg (50percent ee).Similarly, intramolecular cyclization of 2-phenyl>-3,3-dimethyl-4(S)-methoxymethyl-5(S)-phenyloxazolidinium triflate produces, after hydrogenolysis on Pd/C, trans-octahydrophenanthrene with D -51.1 deg (55percent ee).The enantioselection in the cycloaddition with o-quinodimethane intermediate may be accounted for on the basis of ?-stacking interaction in the Diels-Alder transition state.