14400-96-5

Basic information

• Product Name: 4-[[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]methyl]phenol
• Synonyms: 4-[[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]methyl]phenol
• CAS NO: 14400-96-5
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.39
• Mol File: 14400-96-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-[[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]methyl]phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]methyl]phenol(14400-96-5)
• EPA Substance Registry System: 4-[[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]methyl]phenol(14400-96-5)

Safety Data

• Hazardous Substances Data: 14400-96-5(Hazardous Substances Data)

Upstream product

• 36506-66-8 Pakistanamine 
• 16202-66-7 O-methyl-hayatidin 
• 50-00-0 formaldehyd 
• 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 
• 611182-78-6 [4-(bromomethyl)phenoxy][tri(propan-2-yl)]silane 
• 1210-57-7 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 1344118-36-0 (S)-(-)-1-(4-triisopropylsilanyloxy)benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Pakistanine and pakistanamine, two novel dimeric isoquinoline alkaloids.

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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.

Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile

Under controlled conditions, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline- 1-carbonitrile can be quantitatively deprotonated in the α-position. Its alkylation directly furnishes 3,4-dihydroisoquinolines which can serve as starting materials for the preparation of various alkaloids. Here, the preparation of the benzylisoquinolines (+)-laudanidine, (+)-armepavine, and (+)-laudanosine as well as the tetrahydroprotoberberines ( - )-corytenchine and ( - )-tetrahydropseudoepiberberine using Noyori's asymmetric transfer hydrogenation are described. The dimeric alkaloids (+)-O-methylthalibrine and (+)-tetramethylmagnolamine were obtained from nonracemic precursors in Ullmann diaryl ether syntheses.

Kalashine, a novel type aporphine-benzylisoquinoline alkaloid

Berberis orthobotrys produces the new dimer kalashine (1), together with the previously reported pakistanamine (2) and pakistanine (3). Kalashine is the first aporphine-benzylisoquinoline known to be substituted at C-11. Acid catalyzed rearrangement of pa