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

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

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

Downstream Products

• 3486-67-7 palmatine 
• 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 
• 161988-96-1 (2,3-Dimethoxy-benzyl)-[2-(3,4-dimethoxy-phenyl)-ethyl]-[(Z)-2-((R)-2-nitro-benzenesulfinyl)-vinyl]-amine 
• 113557-30-5 N-(3,4-dimethoxybenzyl)-N-(2,3-dimethoxyphenethyl)-α-(methylthio)acetamide 

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 structure-activity relationships of a series of aporphine derivatives with antiarrhythmic activities and acute toxicity

Some aporphine alkaloids, such as crebanine, were found to present arrhythmic activity and also higher toxicity. A series of derivatives were synthesized by using three kinds of aporphine alkaloids (crebanine, isocorydine, and stephanine) as lead compound

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.

Convenient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids

New and convenient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids through the same intermediates was developed. Acylation of the brominated benzylphenethylamine (13) with α- chloro-α-(methylthio)acetyl chloride, followed by cyclization with stannic chloride, furnished the key intermediates 4-methylthio-3- phenethylisoquinolin-3-ones (14), which were methylated to provide their methyl derivatives (17). Both isoquinolin-3-ones (14, 17) were easily transformed into protoberberine alkaloids (16) and their 13-methyl alkaloids (21) in good yield.

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

A NEW AND CONVENIENT SYNTHESIS OF PROTOBERBERINE ALKALOIDS: (+/-)-TETRAHYDROPALMATINE, (+/-)-SINACTINE, (+/-)-CANADINE AND-)-STYLOPINE

2,3,9,10-Tetraoxygenated protoberberine alkaloids (14) were efficiently synthesized from the readily available benzaldehyde (2 or 10) via the benzylphenethylamines (11) and 2-phenethylisoquinolin-3-ones (12 or 13).