47355-66-8

Basic information

• Product Name: N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethanamine
• Synonyms: N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethanamine
• CAS NO: 47355-66-8
• Molecular Formula: C₁₉H₂₅NO₄
• Molecular Weight: 331.4061
• Mol File: 47355-66-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethanamine(47355-66-8)
• EPA Substance Registry System: N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethanamine(47355-66-8)

Safety Data

• Hazardous Substances Data: 47355-66-8(Hazardous Substances Data)

Upstream product

• 1521-38-6 2,3-dimethoxybenzoic acid 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 109806-78-2 N-(2,3-dimethoxybenzylidene)-2-(3,4-dimethoxyphenyl)ethanamine 

Downstream Products

• 483-14-7 tetrahydropalmatine 
• 102321-59-5 N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethan-1-aminium chloride 
• 2934-97-6 (+/-)-tetrahydropalmatine 
• 113557-32-7 7,8-dimethoxy-3-(2,3-dimethoxybenzyl)-1-methylthio-1,2,4,5-tetrahydrobenzazepin-2-one 
• 113557-31-6 N-(3,4-dimethoxybenzyl)-N-(2,3-dimethoxyphenethyl)-α-(methylsulfinyl)acetamide 
• 113575-52-3 7,8-dimethoxy-2-(3,4-dimethoxybenzyl)-4-methylthio-1,2,3,4-tetrahydroisoquinolin-3-one 
• 113557-41-8 7,8-dimethoxy-2-(3,4-dimethoxyphenethyl)-1,2,3,4-tetrahydroisoquinolin-3-one 
• 26067-60-7 2,3,9,10-tetramethoxy-5,8-dihydro-6H-isoquinolino[3,2-α]isoquinoline 
• 113557-30-5 N-(3,4-dimethoxybenzyl)-N-(2,3-dimethoxyphenethyl)-α-(methylthio)acetamide 
• 3486-67-7 palmatine 
• 161988-96-1 (2,3-Dimethoxy-benzyl)-[2-(3,4-dimethoxy-phenyl)-ethyl]-[(Z)-2-((R)-2-nitro-benzenesulfinyl)-vinyl]-amine 

Relevant articles and documents

Total Synthesis of (-)-Canadine, (-)-Rotundine, (-)-Sinactine, and (-)-Xylopinine Using a Last-Step Enantioselective Ir-Catalyzed Hydrogenation

A concise asymmetric total synthesis of a group of tetrahydroprotoberberine alkaloids, (-)-canadine, (-)-rotundine, (-)-sinactine, and (-)-xylopinine, has been accomplished in three steps from the commercially available corresponding disubstituted phenylethylamine and disubstituted benzaldehyde. Our synthesis toward these four alkaloids took advantage of the following strategy: In the first step, we achieved an efficient and sustainable synthesis of secondary amine hydrochlorides via a fully continuous flow; in the second step, we developed a Pictet-Spengler reaction/Friedel-Crafts hydroxyalkylation/dehydration cascade for the construction of the dihydroprotoberberine core structure (ABCD-ring); and in the last step, Ir-catalyzed enantioselective hydrogenation was employed for the introduction of the desired stereochemistry at the C-14 position in the tetrahydroprotoberberine alkaloids. This work significantly expedites the asymmetric synthesis of the entire tetrahydroprotoberberine alkaloid family as well as a more diverse set of structurally related non-natural analogues.

Synthesis and antihyperglycemic evaluation of various protoberberine derivatives

Various berberine derivatives (2-17) were synthesized and their antihyperglycemic activities were evaluated in a model of β-cell-membrane chromatography and a model of alloxan-induced diabetes mice. The results indicated that compounds 5 and 14 exhibited antihyperglycemic activity. Their structure-activity relationships were discussed.

Chiral acetylenic sulfoxides in organic synthesis: Secondary amine cyclization and total synthesis of (S)-(-)-carnegine

Michael addition of secondary amines 1b-1g onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded structures of tetrahydroisoquinoline skeleton in high to moderate diastereoselectivity. Optical pure (S)-(-)-carnegine has been sy