26503-67-3

Basic information

• Product Name: (S)-1,2,3,5,8,8a-hexahydro-6,7-bis(3,4-dimethoxy-phenyl)indolizine
• CAS NO: 26503-67-3
• Molecular Weight: 395.499
• Mol File: 26503-67-3.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: (S)-1,2,3,5,8,8a-hexahydro-6,7-bis(3,4-dimethoxy-phenyl)indolizine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2,3,5,8,8a-hexahydro-6,7-bis(3,4-dimethoxy-phenyl)indolizine(26503-67-3)
• EPA Substance Registry System: (S)-1,2,3,5,8,8a-hexahydro-6,7-bis(3,4-dimethoxy-phenyl)indolizine(26503-67-3)

Safety Data

• Hazardous Substances Data: 26503-67-3(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 77513-56-5 (+/-)-6,7-di(3-hydroxy-4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizine 
• 2859-78-1 4-Bromoveratrole 
• 138207-09-7 Trifluoro-methanesulfonic acid 6-bromo-1,2,3,5,8,8a-hexahydro-indolizin-7-yl ester 
• 138207-05-3 Trifluoro-methanesulfonic acid 6-(3,4-dimethoxy-phenyl)-1,2,3,5,8,8a-hexahydro-indolizin-7-yl ester 
• 76787-76-3 6,7-Di(3',4'-dimethoxyphenyl)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizine 
• 156424-91-8 6,7-bis-(3,4-dimethoxyphenyl)-1,2,3-trihydroindolizine-5-one 
• 184221-07-6 3-[4,5-Bis-(3,4-dimethoxy-phenyl)-pyridin-2-yl]-propan-1-ol 
• 60890-29-1 (3,4-dimethoxybenzoyl)acetic acid 
• 60890-27-9 1-(3,4-dimethoxyphenyl)-2-(pyrrolidin-2-yl)ethan-1-one 
• 74053-93-3 methyl 3-(3,4-dimethoxyphenyl)-3-oxopropionate 
• 76787-77-4 1-(3,4-Dimethoxyphenyl)-2-<1-<(3,4-dimethoxyphenyl)acetyl>pyrrolidin-2-yl>ethanone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 159730-37-7 1-(3,4-dimethoxyphenyl)-2-methoxyethylene 

Downstream Products

• 30061-35-9 Tylocrebrin 
• 90243-12-2 2,3,6,7-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline 
• 25908-92-3 2,3,6,7-Tetramethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopenta[b]triphenylene 

Relevant articles and documents

A Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade: Concise Synthesis of (±)-seco-Antofine and (±)-Septicine

A concise and flexible procedure for the synthesis of highly functionalized N-heterocyclic 1,6-annulated 2-pyridones and 2,3-annulated 4-pyrimidinones has been elaborated through a gold-catalyzed tandem hydroamination/cycloisomerization cascade. This novel and highly efficient method allows the rapid construction of these diverse N-heterocyclic scaffolds starting from readily available building blocks, and shows a wide scope and good functional group tolerance. The total synthesis of (±)-seco-antofine and (±)-septicine were realized employing this strategy.

Formal Synthesis of Indolizidine and Quinolizidine Alkaloids from Vinyl Cyclic Carbonates

Cyclic carbonates have long been considered relatively inert molecules acting as protecting groups in complex multistep synthetic routes. This study shows that a concise, yet modular synthesis of indolizidine and quinolizidine alkaloids can be developed from vinyl-substituted cyclic carbonate (VCC) intermediates. Through a highly stereoselective palladium-catalyzed allylic alkylation reaction, these alkaloid motifs can be assembled in four synthetic and only two column purification steps. The combined results help to further advance functionalized cyclic carbonates as useful and reactive intermediates in natural product synthesis.

Cyano Group Removal from Cyano-Promoted Aza-Diels-Alder Adducts: Synthesis and Structure-Activity Relationship of Phenanthroindolizidines and Phenanthroquinolizidines

Phenanthroindolizidines and phenanthroquinolizidines were concisely synthesized by the reductive decyanization of cyano-promoted intramolecular aza-Diels-Alder cycloadducts followed by aryl-aryl coupling. Cyano groups were removed from α-aminoacrylonitriles via treatment with sodium borohydride in 2-propanol in almost quantitative yields; a possible mechanism was proposed and examined using D-labeling experiments. A systematic study of the effects of the phenanthrene substitution pattern on the anticancer activity against three human cancer cell lines was discussed. (Chemical Equation Presented).