3423-02-7

Basic information

• Product Name: l-O-Methylarmepavine
• Synonyms: [1S,(+)]-1,2,3,4-Tetrahydro-6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-2-methylisoquinoline;l-O-Methylarmepavine;N,O,O'-Trimethylcoclaurine
• CAS NO: 3423-02-7
• Molecular Formula: C₂₀H₂₅NO₃
• Molecular Weight: 327.4174
• Mol File: 3423-02-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: l-O-Methylarmepavine(CAS DataBase Reference)
• NIST Chemistry Reference: l-O-Methylarmepavine(3423-02-7)
• EPA Substance Registry System: l-O-Methylarmepavine(3423-02-7)

Safety Data

• Hazardous Substances Data: 3423-02-7(Hazardous Substances Data)

Upstream product

• 518-34-3 Tetrandrin 
• 1246431-52-6 C₁₉H₁₇Cl₃O₇ 
• 1580442-46-1 C₅₃H₅₈N₂O₈ 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 228271-22-5 6,7-dimethoxy-1-[[4-[5-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinyl)methyl-2-methoxy]phenoxy]benzyl]-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 409366-27-4 (3,5-dichloro-4-hydroxyphenyl)acetic acid methyl ester 
• 42583-41-5 2-{4-[5-(carboxymethyl)-2-methoxyphenoxy]phenyl}acetic acid 
• 1580442-44-9 methyl 2-{4-hydroxy-3-[4-(2-methoxy-2-oxoethyl)phenoxy]phenyl}acetate 
• 1246431-54-8 C₁₈H₁₅Cl₃O₆ 
• 87183-74-2 (+)-Vanuatine 
• 93780-79-1 (+)-thaliphylline 
• 182305-80-2 {(S)-1-[(S)-6,7-Dimethoxy-1-(4-methoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-pyrrolidin-2-yl}-methanol 
• 3611-33-4 O,O-Dimethylcoclaurine 
• 182305-82-4 (9R,13S)-2,3-Dimethoxy-6,9,13,15,16,17-hexahydro-7H,12H-11-oxa-8,14-diaza-cyclopenta[a]phenanthrene 

Relevant articles and documents

Practical metal-free C(sp3)-H functionalization: Construction of structurally diverse α-substituted N-benzyl and N-allyl carbamates

Described is a practical and universal C-H functionalization of readily removable N-benzyl and N-allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3CClO4. The metal-free reaction has an excellent functional-group tolerance, and displays a broad scope with respect to both N-carbamates and nucleophile partners (a variety of organoboranes and C-H compounds). The synthetic utility in target- as well as diversity-oriented syntheses is demonstrated. Strategic play: A direct functionalization of the title carbamates with a wide range of nucleophiles has been developed. The reaction proceeds efficiently at low temperature using Ph3CClO4 as an oxidant. Sensitive functional groups are tolerated, thus allowing applications in natural product synthesis, the construction of chemical libraries, and the discovery of potential anticancer targets.

Lewis acid-mediated nucleophilic alkylations on chiral [6,3a,4]oxadiazaindano[5,4-a]isoquinolines. Asymmetric synthesis of 1-alkyl substituted tetrahydroisoquinolines

Lewis acid-mediated nucleophilic alkylation of the chiral [6,3a,4]oxadiazaindano[5,4-a]isoquinoline derivatives with various organometallic reagents leads to highly enantioselective synthesis of 1-alkyl substituted tetrahydroisoquinolines. This methodology was applied to the asymmetric synthesis of (-)-salsolidine and (+)-O-methylarmepavine.

ENZYMIC CONTROL OF STEREOCHEMISTRY AMONG THE THALICTRUM BISBENZYLISOQUINOLINE ALKALOIDS

The new bisbenzylisoquinolines (+)-thaligrisine and (+)-thaliphylline 6 have been isolated from Thalictrum minus var. microphyllum.Four rules are described which correlate the structures os Thalictrum bisbenzylisoquinolines with their stereochemistry at C-1 and C-1'.As a result, (+)-thalrugosamine is shown to be identical with (+)-homoaromoline 14. (+)-Thalisamine and (+)-N'-norhernandezine are also identical and are represented by expression 18.The sole exception to the rules is (-)-isothalidezine 15.