5320-36-5

Usage

Chemical class

Naphthalenes

Physical state

White solid

Common uses

Organic synthesis and pharmaceutical research

Structural features

Three methoxy groups attached to the 1, 2, and 3 positions of the naphthalene ring
A trimethoxyphenyl group attached to the 7 position

Potential applications

Development of pharmaceutical drugs and study of the structure and function of organic molecules

Safety precautions

Handle and use with caution due to potential health and safety risks when not properly handled

Versatility

Various potential uses in both industrial and scientific fields

Upstream product

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 182217-53-4 1,2,3-trimethoxy-5-(2-methoxyvinyl)benzene 
• 5320-31-0 3,4,5-trimethoxyphenylacetaldehyde 
• 569-77-7 purpurogallin 

Downstream Products

• 1240372-44-4 7-(3,4,5-trihydroxyphenyl)naphthalene-1,2,3-triol 

Relevant academic research and scientific papers

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.

Facile access to methoxylated 2-phenylnaphthalenes and epoxydibenzocyclooctenes

Methoxylated phenylethanals were treated with concentrated hydrochloric acid in 1,4-dioxane to give methoxylated 2-phenylnaphthalenes or 1,2,9,10-tetrahydro-1,9-epoxydibenzo[a,e]cyclooctenes. Yields in 2-phenylnaphthalenes were quite good and 1,2,9,10-tetrahydro-1,9-epoxydibenzo[a, e]cyclooctenes could be easily isolated. 2-Phenylnaphthalenes were obtained by a tandem aldol condensation-intramolecular Friedel-Crafts cyclisation and 1,2,9,10-tetrahydro-1,9-epoxydibenzo[a,e]cyclooctenes by a O-condensation followed by a double intramolecular Friedel-Crafts alkylation.