3860-46-6

Basic information

• Product Name: (-)-β-Narcotine
• Synonyms: (3R)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone;(3R)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]isobenzofuran-1(3H)-one;L-β-Narcotine
• CAS NO: 3860-46-6
• Molecular Formula: C₂₂H₂₃NO₇
• Molecular Weight: 413.42052
• Mol File: 3860-46-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 565.3°Cat760mmHg
• Flash Point: 295.7°C
• Appearance: /
• Density: 1.332g/cm³
• CAS DataBase Reference: (-)-β-Narcotine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-β-Narcotine(3860-46-6)
• EPA Substance Registry System: (-)-β-Narcotine(3860-46-6)

Safety Data

• Hazardous Substances Data: 3860-46-6(Hazardous Substances Data)

Upstream product

• 35933-62-1 1S,9S β-narcotine 
• 5780-07-4 3-methoxy-4,5-methylenedioxybenzaldehyde 
• 15896-78-3 (E)-4-methoxy-6-(2-nitrovinyl)benzo[d][1,3]dioxole 
• 23693-38-1 β-(3-methoxy-4,5-methylenedioxy)phenylethylamine 
• 121-33-5 vanillin 
• 1449378-31-7 tert-butyl [2-(7-methoxybenzo[d][1,3]dioxol-5-yl)ethyl]carbamate 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 569-31-3 meconin 
• 73563-23-2 3-bromo-6,7-dimethoxyphthalide 
• 519-05-1 opianic acid 
• 62059-59-0 methyl 6-formyl-2,3-dimethoxybenzoate 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 36017-64-8 (±)-β-N-demethyl noscapine 

Downstream Products

• 569-31-3 meconin 
• 82-54-2 4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol 
• 483-89-6 2,3-dimethoxy-6-{[4-methoxy-6-(2-methylamino-ethyl)-benzo[1,3]dioxol-5-yl]-acetyl}-benzoic acid 
• 128-62-1 (±)-β-noscapine 
• 519-05-1 opianic acid 
• 550-10-7 hydrocotarnine 
• 128-62-1 noscapine 
• 68353-55-9 (S)-7-hydroxy-6-methoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo-[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one 
• 69937-26-4 (3,4-dimethoxy-2-methyl-phenyl)-(4-methoxy-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-methanone 

Relevant articles and documents

An Acid-Catalyzed Epoxide Ring-Opening/Transesterification Cascade Cyclization to Diastereoselective Syntheses of (±)-β-Noscapine and (±)-β-Hydrastine

An acid-catalyzed stereoselective epoxide ring-opening/intramolecular transesterification cascade cyclization reaction and N-Boc deprotection was found to be a successful strategy to construct the phthalide tetrahydroisoquinoline skeleton in one pot. Based on this strategy, the unified and highly diastereoselective routes for the total syntheses of (±)-β-Noscapine and (±)-β-Hydrastine were exploited.

Blocking group-directed diastereoselective total synthesis of (±)-α-noscapine

A new approach for the diastereoselective synthesis of (±)-α- noscapine, a phthalide tetrahydroisoquinoline alkaloid exhibiting several biological activities, is described. The strategy features a blocking group-directed Bischler-Napieralski reaction followed by diastereoselective reduction (α/β>23:1). One of the key intermediates, phthalide-3-carboxylic acid, could be efficiently prepared from simple benzoic acid derivative and glyoxylic acid in one-pot.

Novel Zinc-Promoted Alkylation of Iminium Salts. New Synthesis of Benzylisoquinoline, Phthalidylisoquinoline, and Protoberberine Alkaloids and Related Compounds

Zinc-promoted reductive coupling reaction of iminium salts with alkyl halides was found to be a successful key reaction for synthesis of a variety of alkaloids such as benzylisoquinoline, phthalidylisoquinoline, and protoberberine alkaloids.More specifically, laudanosine, cordrastine, hydrastine, narcotine, tetrahydropalmatine, and canadine were obtained.A new route for the synthesis of the emetine and yohimbine skeletons was exploited.