5544-50-3

Basic information

• Product Name: 5-(3,4-dimethoxybenzyl)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline
• Synonyms: 5-(3,4-dimethoxybenzyl)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline
• CAS NO: 5544-50-3
• Molecular Weight: 341.407
• Mol File: 5544-50-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-(3,4-dimethoxybenzyl)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3,4-dimethoxybenzyl)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline(5544-50-3)
• EPA Substance Registry System: 5-(3,4-dimethoxybenzyl)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline(5544-50-3)

Safety Data

• Hazardous Substances Data: 5544-50-3(Hazardous Substances Data)

Upstream product

• 19918-74-2 5-[(3,4-dimethoxyphenyl)methyl]-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline 
• 74-88-4 methyl iodide 
• 65628-87-7 6-methyl[1,3]dioxolo[4,5-g]isoquinoline-5,7(6H,8H)-dione 
• 28281-84-7 2-carboxy-4,5-methylenedioxyphenylacetic acid 
• 135798-21-9 C₁₁H₁₃BF₃NO₂ 
• 494-55-3 N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 51486-66-9 5-(3,4-dimethoxybenzyl)-6,6-dimethyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide 

Relevant articles and documents

Total Synthesis of Tetrahydroisoquinoline-Based Bioactive Natural Products Laudanosine, Romneine, Glaucine, Dicentrine, and Their Unnatural Analogues Isolaudanosine and Isoromneine

Starting from suitably substituted homophthalic acids, total synthesis of titled alkaloids have been demonstrated in very good yields. The obtained natural products laudanosine and romneine were utilized to accomplish synthesis of two isoquinoline-based alkaloids glaucine and dicentrine. Base-induced selective generation of two different types of benzylic carbanions, their coupling reactions with 3,4-dimethoxybenzyl mesylate, and the regioselective iodination followed by intramolecular aryl-aryl coupling reactions to form the fused biaryl systems were the strategic steps.

Synthesis of Benzyltetrahydroisoquinoline Alkaloids with the Use of 1,3-Dithianes of Aromatic Aldehydes

A practical synthesis of 1-benzyl-2-methyl-1,2,3,4-tetrahydroisoquinolines (4) is described. Condensation of 6,7-disubstituted N-methyl-3,4-dihydroisoquinolinium iodide 1 with 1,3-dithianes 2 gave addition products 3 from which alkaloids 4 were obtained by desulfuration. Key words: 1-benzyltetrahydroisoquinolines, dithianes, tetrahydroisoquinolinium alkaloids