4747-98-2

Basic information

• Product Name: (S)-(-)-Tetrahydropapaverine
• Synonyms: (S)-(-)-TETRAHYDROPAPAVERINE;(1S)-1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline;(1S)-1,2,3,4-tetrahydro-6,7-dimethoxy -1-[(3,4-dimethoxyphenyl)methyl]Isoquinoline;(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-1α-(3,4-dimethoxybenzyl)isoquinoline;(S)-1-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;(S)-Norlaudanosine;[1S,(-)]-6,7-Dimethoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline;(S)-2-((S)-1-(2-chlorophenyl)ethyl)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 4747-98-2
• Molecular Formula: C₂₀H₂₅NO₄
• Molecular Weight: 343.42
• Product Categories: Heterocyclic Compounds;Chirals;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 4747-98-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 80-82 °C
• Boiling Point: 475.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.120
• Solubility: Chloroform, DMSO, Methanol
• PKA: 8.66±0.40(Predicted)
• CAS DataBase Reference: (S)-(-)-Tetrahydropapaverine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-Tetrahydropapaverine(4747-98-2)
• EPA Substance Registry System: (S)-(-)-Tetrahydropapaverine(4747-98-2)

Safety Data

• Hazardous Substances Data: 4747-98-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 4747-98-2 differently. You can refer to the following data:
1. (S)-(-)-Tetrahydropapaverine can be used in the enantioselective.
2. Used in the enantioselective synthesis of (+)-(S)-Laudanosine (L178525) and (-)-(S)-Xylopinine.

Upstream product

• 114105-61-2 (S)-1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-2-((R)-1-phenyl-ethyl)-1,2,3,4-tetrahydro-isoquinoline 
• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 50896-90-7 (-) N-norlaudanosine 
• 132283-68-2 2-(2-chloroethyl)-4,5-dimethoxybenzaldehyde 
• 52806-46-9 1-bromo-4,5-dimethoxy-2-methylbenzene 
• 1309831-74-0 (S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide 
• 1309831-72-8 (S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene 
• 1309831-82-0 (1S)-1-[4,5-dimethoxy-2-[(R)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1309831-77-3 (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1309831-80-8 (1S)-1-[4,5-dimethoxy-2-[(R)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline 
• 1309831-76-2 (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline 
• 114105-58-7 1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-2-((S)-1-phenyl-ethyl)-3,4-dihydro-isoquinolinium; chloride 
• 114105-54-3 2-(3,4-Dimethoxy-phenyl)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-N-((S)-1-phenyl-ethyl)-acetamide 
• 114105-64-5 (S)-(+)-2-(3,4-dimethoxyphenyl)-N-(1-phenylethyl)acetamide 

Downstream Products

• 2688-77-9 (S)-laudanosine 
• 523-02-4 (S)-(-)-norcoralydine 
• 145487-46-3 (+)-N,N'-4,11-dimethyl-4,11-diaza-3,12-dioxotetramethylene-1,14-diyl-bis(S)-tertahydropapaverine 
• 57651-56-6 (S)-1-<(3,4-Dimethoxyphenyl)methyl>-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1344118-31-5 (S)-(+)-1-(2-bromo-4,5-dimethoxybenzyl)-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 4829-34-9 (S)-(+)-1-(2-bromo-4,5-dimethoxybenzyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 50720-57-5 (S)-(-)-norlaudanosine (-)-N-acetyl-L-leucine 
• 64493-09-0 (RS)/meso-N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-tetrahydropapaverine 
• 64229-38-5 (RS)/meso-N,N'-4,7-dioxa-3,8-dioxodecylene-1,10-diyl-bis-tetrahydropapaverine 
• 64229-34-1 N,N'-4,7-dioxa-3,8-dioxodecylene-1,10-diyl-bis-(S)-(+)-tetrahydropapaverine 

Relevant articles and documents

Asymmetric total synthesis of (?)-javaberine A and (?)-epi-javaberine A based on catalytic intramolecular hydroamination of N-methyl-2-(2-styrylaryl)ethylamine

Asymmetric total synthesis of (?)-javaberine A and its epimer was achieved by utilizing two methods for isoquinoline synthesis, asymmetric hydroamination of N-methyl-2-(2-styrylaryl)ethylamine and Bischler-Napieralski cyclization. Intramolecular asymmetric hydroamination of N-methyl aminoalkene 4 was catalyzed by lithium amide–chiral bisoxazoline to give tetrahydroisoquinoline (S)-laudanosine with good enantioselectivity in excellent yield. N-Demethylation of (S)-laudanosine was accomplished by Polonovski-type reaction to give (S)-norlaudanosine. Condensation of (S)-norlaudanosine with homoveratric acid, and subsequent Bischler-Napieralski cyclization, LiAlH4 reduction, and O-demethylation furnished (8R,14S)-(?)-javaberine A, corresponding to antipode of natural javaberine A. (8S,14S)-(?)-Javaberine A, which corresponds to C14-epimer of natural javaberine A, was also successfully synthesized.

Synthesis of Tetrahydroisoquinoline Alkaloids and Related Compounds through the Alkylation of Anodically Prepared α-Amino Nitriles

α-Amino nitrile 2a was conveniently prepared in two individual steps from chiral hexafluorophosphate salt isoquinolinium (-)-8b including anodic cyanation as an efficient means to activate the sp3 C1-H bond of the THIQ nucleus. The lithiation o

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.