16804-85-6

Basic information

• Product Name: 1,2,3,4,4a,10a-hexahydrophenanthrene
• CAS NO: 16804-85-6
• Molecular Formula: C₁₄H₁₆
• Molecular Weight: 184.2768
• Mol File: 16804-85-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 307°C at 760 mmHg
• Flash Point: 131.4°C
• Density: 1.015g/cm³
• Vapor Pressure: 0.00135mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: 1,2,3,4,4a,10a-hexahydrophenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,4a,10a-hexahydrophenanthrene(16804-85-6)
• EPA Substance Registry System: 1,2,3,4,4a,10a-hexahydrophenanthrene(16804-85-6)

Safety Data

• Hazardous Substances Data: 16804-85-6(Hazardous Substances Data)

Usage

General Description

1,2,3,4,4a,10a-hexahydrophenanthrene is a polycyclic hydrocarbon compound with a molecular formula of C14H16. It is a colorless, oily liquid with a faint odor and is insoluble in water. This chemical is produced during the high-temperature pyrolysis of certain hydrocarbons and can be found in coal tar and petroleum. It is also used in the synthesis of various pharmaceuticals and organic compounds. 1,2,3,4,4a,10a-hexahydrophenanthrene is known for its potential health hazards and should be handled with caution, as inhalation or skin contact can lead to irritation and other adverse effects.

Upstream product

• 25662-65-1 1,2,3,4,4a,9,10,10a-Octahydro-phenanthrol-⁽⁹⁾ 
• 17040-65-2 1-cyclohexenyl(phenyl)methanone 
• 36702-38-2 5,6-dihydro-[1,1'-biphenyl]-2(1H)-one 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 84694-53-1 8,9-trans-6-<2-(dimethylamino)-1(R)-phenylethoxy>octahydrophenanthrene 
• 25662-65-1 trans-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-ol 
• 52092-27-0 (+/-)-(cis-2-phenyl-cyclohexyl)-acetic acid 
• 1203-67-4 cis-1,2,3,4,4a,9a-hexahydro-9H-fluoren-9-one 
• 110-83-8 cyclohexene 
• 19634-93-6 cis-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-one 
• 52092-27-0 trans-(2-phenylcyclohexyl)acetic acid 
• 21656-46-2 trans-1,2,3,4,4a,10a-hexahydro-9(10H)-phenanthrenone 
• 80738-31-4 <(1S*,2R*)-3-oxo-2-phenylcyclohexyl>acetic acid 

Downstream Products

• 53446-96-1 (4aR,9R,10S,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-phenanthrene-9,10-diol 
• 53446-99-4 (4aR,9S,10S,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-phenanthrene-9,10-diol 
• 28352-34-3 syn-9.10-Epoxy-1.2.3.4.4a.9.10.10a-(trans-4a.10a)-octahydrophenanthren 
• 53446-97-2 (4aR,9S,10R,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-phenanthrene-9,10-diol 
• 28352-32-1 (1aR,1bR,5aR,9bS)-1a,1b,2,3,4,5,5a,9b-Octahydro-1-oxa-cyclopropa[l]phenanthrene 

Relevant articles and documents

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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.