4781-58-2

Basic information

• Product Name: Nor Reticuline
• Synonyms: (-)-(S)-N-Norreticuline;(1S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-Methoxyphenyl)Methyl]-6-Methoxy-7-isoquinolinol;(S)-Norreticuline;2-DeMethylreticuline
• CAS NO: 4781-58-2
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.36364
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 4781-58-2.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Nor Reticuline(CAS DataBase Reference)
• NIST Chemistry Reference: Nor Reticuline(4781-58-2)
• EPA Substance Registry System: Nor Reticuline(4781-58-2)

Safety Data

• Hazardous Substances Data: 4781-58-2(Hazardous Substances Data)

Upstream product

• 74-88-4 methyl iodide 
• 104621-41-2 (Z)-7-Acetoxy-1-<(3-acetoxy-4-methoxyphenyl)methylene>-2-acetyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 72072-54-9 (S)-6,7-dihydroxy-1-(3',4'-dihydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide 
• 485-19-8 (+)-(S)-reticuline 
• 21411-21-2 1,2-dehydroreticulinium iodide 
• 18694-10-5 1-(3'-hydroxy-4'-methoxybenzyl)-6,7-dimethoxyisoquinoline 
• 57231-35-3 4',6-O,O-dimethylpapaveroline 
• 13168-51-9 N-benzoyl-norreticuline 
• 72258-91-4 1,2-dehydronorreticuline 
• 76318-96-2 C₁₈⁽¹⁴⁾CH₂₃NO₄ 

Relevant articles and documents

Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids

(Figure Presented) A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.