167026-40-6

Basic information

• Product Name: (1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol
• Synonyms: (1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol
• CAS NO: 167026-40-6
• Molecular Weight: 293.193
• Mol File: 167026-40-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol(167026-40-6)
• EPA Substance Registry System: (1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol(167026-40-6)

Safety Data

• Hazardous Substances Data: 167026-40-6(Hazardous Substances Data)

Upstream product

• 79560-19-3 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one 
• 95-50-1 1,2-dichloro-benzene 
• 90-15-3 α-naphthol 
• 124379-29-9 (4S)-4-(3,4-dichlorophenyl)-1-tetralone 
• 195388-54-6 (R)-4-tert-butyl(4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-1-yloxy)diphenylsilane 
• 1026451-65-9 tert-Butyl-((R)-3,4-dibromo-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-diphenyl-silane 
• 195388-53-5 (R)-4-bromo-1-tert-butyldiphenylsiloxy-1,2-dihydro-naphthalene 
• 195388-52-4 (R)-1-tert-butyldiphenylsiloxy-1,2-dihydro-naphthalene 
• 123849-23-0 (R)-(+)-1-hydroxy-1,2-dihydronaphthalene 
• 439134-46-0 1-(3,4-dichlorophenyl)-1,2-dihydronaphthalene 
• 195388-55-7 (+)-(1R)-4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-1-ol 

Downstream Products

• 87857-41-8 norsertraline 
• 79617-96-2 Sertraline 
• 79951-46-5 trans-(1R,4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 312620-93-2 (S)-N-(4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-ylidene)methanamine 
• 195388-56-8 (1S,4S)-1-azido-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalene 
• 124379-29-9 (4S)-4-(3,4-dichlorophenyl)-1-tetralone 

Relevant articles and documents

Chemoenzymatic Synthesis of Sertraline

A chemoenzymatic approach has been developed for the preparation of sertraline, an established anti-depressant drug. Ketoreductases (KREDs) were employed to yield a key chiral precursor. The bioreduction of the racemic tetralone exhibited excellent enantioselectivity (>99 % ee) and diastereomeric ratio (99:1) at 29 % conversion (the maximum theoretical yield is 50 %) after 7 hours. The resulting (S,S)-alcohol was efficiently oxidized to an enantiopure (S)-ketone, an immediate precursor of sertraline, by using sodium hypochlorite as oxidant and 2-azaadamantane N-oxyl (AZADO) as organocatalyst. Alternative routes aiming at the direct biocatalytic amination using imine reductases and transaminases were unsuccessful.

Efficient kinetic resolution in hydroboration of 1,2-dihydronaphthalenes

1-Substituted 1,2-dihydronaphthalenes undergo kinetic resolution during asymmetric hydroboration with Rh-QUINAP complexes.

General strategy toward the tetrahydronaphthalene skeleton. An expedient total synthesis of sertraline

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