2884-83-5

Basic information

• Product Name: (+)-stylopine
• CAS NO: 2884-83-5
• Molecular Weight: 323.348
• Mol File: 2884-83-5.mol
• Article Data: 24

Chemical Properties

• CAS DataBase Reference: (+)-stylopine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-stylopine(2884-83-5)
• EPA Substance Registry System: (+)-stylopine(2884-83-5)

Safety Data

• Hazardous Substances Data: 2884-83-5(Hazardous Substances Data)

Upstream product

• 41431-72-5 rac-7-methyl-2,3;9,10-bis-methylenedioxy-berbinium; chloride 
• 58995-64-5 1-(N,N-dimethylaminomethyl)-3,4-(methylenedioxy)benzene 
• 106544-63-2 (2-((tert-butyldimethylsiloxy)methyl)-3,4-(methylenedioxy)benzyl)trimethylsilane 
• 106544-57-4 N,N-dimethyl-2-((tert-butyldimethylsiloxy)methyl)-3,4-(methylenedioxy)benzylamine 
• 106544-62-1 2-((tert-butyldimethylsiloxy)methyl)-3,4-(methylenedioxy)benzyl chloride 
• 87167-69-9 N,N-dimethyl-2-(hydroxymethyl)-3,4-(methylenedioxy)benzylamine 
• 106544-64-3 2,3-(methylenedioxy)-6-((trimethylsilyl)methyl)benzyl iodide 
• 106544-67-6 2,3-(methylenedioxy)-6-((trimethylsilyl)methyl)benzyl alcohol 
• 106544-66-5 2-(2,3-(methylenedioxy)-6-((trimethylsilyl)methyl)benzyl)-6,7-(methylenedioxy)-3,4-dihydroisoquinolinium perchlorate 
• 247579-59-5 1-[2-bromo-3,4-(methylenedioxy)benzyl]-6,7-(methylenedioxy)-3,4-dihydroisoquinoline 
• 247579-86-8 1-[2-bromo-3,4-(methylenedioxy)benzyl]-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline 
• 247579-56-2 N-[(3,4-methylenedioxy)phenethyl]-2-bromo-3,4-(methylenedioxy)phenylacetamide 
• 247579-53-9 (4-bromo-benzo[1,3]dioxol-5-yl)-acetyl chloride 
• 247579-50-6 2-bromo-3,4-(methylenedioxy)benzyl alcohol 

Downstream Products

• 6020-18-4 coptisine chloride 
• 49870-84-0 corydamine 
• 130-86-9 protopine 

Relevant articles and documents

Fumaria densiflora DC. Alkaloids

Twenty isoquinoline alkaloids were identified in the aerial part of Fumaria densiflora DC. In addition to bicuculline, densiflorine, fumaritine, fumariline, scoulerine, coptisine, cryptopine, parfumine, protopine, and sinactine which have been found previously, the following alkaloids were isolated for the first time from this species: adlumine, fumaricine, fumaritridine, fumarophycine, fumarofine, corytuberine, cis-N-methylstylopinium iodide, stylopine, and two new 1-benzylisoquinoline alkaloids, viz. fumaflorine and fumaflorine methyl ester. The cytoprotectivity of extracts of F. densiflora and F. officinalis, and that of protopine, cryptopine, and parfumine was tested on primary cultures of rat hepatocytes intoxicated with carbon tetrachloride. The cytoprotective effect of the extracts is associated with the alkaloids.

From protopines to berbines: Synthesis of 1-methoxystylopine and its N-metho salts from coulteropine

The transformation of protopines into berbines under improved conditions has been used to synthesize 1-methoxystylopine. Coulteropine, the main alkaloid from Romneya coulteri, was used as the starting protopine to accomplish the stereocontrolled synthesis of both cis and trans N-methyl-1-methoxystylopinium salts. The results of ab initio calculations (B3LYP/6-31G**) which are consistent with experimental data, sustain the influence of the C-1 substituent on both the conformational equilibrium of berbines and the rate of N-methylation.

Berberine type alkaloid production (by machine translation)

[Problem] to efficiently produce the alkaloid production-type alkaloid berberine berberine. 2, 6 - Di - tert - butyl -4 - methylpyridine [solution] trifluoromethanesulfonic anhydride with certain compound after the intramolecular cyclization reaction, after reduction, de-bromo, quinone oxidants including a step of the manufacturing method of an aromatic ring. Figure 1 [drawing] (by machine translation)

A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps

A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A3 reaction, Pd-catalyzed reductive carbocyclization, and PtO2-catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.