3122-95-0

Basic information

• Product Name: (S)-Laudanine
• Synonyms: (S)-Laudanine;2-Methoxy-5-[[(1S)-1,2,3,4-tetrahydro-6,7-diMethoxy-2-Methyl-1-isoquinolinyl]Methyl]-
• CAS NO: 3122-95-0
• Molecular Formula: C₂₀H₂₅NO₄
• Molecular Weight: 343.4168
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 3122-95-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-Laudanine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Laudanine(3122-95-0)
• EPA Substance Registry System: (S)-Laudanine(3122-95-0)

Safety Data

• Hazardous Substances Data: 3122-95-0(Hazardous Substances Data)

Usage

Uses

An alkaloid from Xylopia championii as antioxidant and antifungal agent.

Upstream product

• 119533-72-1 (S)-1-(3-benzoyloxy-4-methoxy-benzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline 
• 87183-78-6 (+)-O,O,O-Trimethylvateamine 
• 87183-75-3 (+)-Vateamine 
• 1344118-32-6 4-methoxy-3-(triisopropylsilanyloxy)benzyl bromide 
• 1344118-29-1 1-(4-methoxy-3-triisopropylsilyloxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1344118-38-2 (S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1344118-30-4 (S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1210-57-7 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 865-50-9 iodomethane-d3 

Downstream Products

• 59654-05-6 (+)-O-methylthalibrine 

Relevant articles and documents

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.

Novel Biogenetic Pathways from (+)-Reticuline. Three Dimeric Alkaloids: (+)-Vanuatine, (+)-Vateamine, and (+)-Malekulatine

The bark of Hernandia peltata Meissner (Hernandiaceae), gathered in the Republic of Vanuatu (New Hebrides), has yielded the bis(benzylisoquinolines) (+)-vanuatine (5), (+)-vateamine (6), and (+)-malekulatine (7).These are the first-known dimers of (+)-reticuline (2).Compounds 5 and 6 are products of tail-to-tail oxidative coupling, whereas 7 involves head-to-tail coupling.