26294-41-7

Usage

Uses

1. Used in Pharmaceutical Industry:
Ipalbidine is used as a pharmaceutical compound for its potential therapeutic applications. The alkaloid's unique structure and properties make it a promising candidate for the development of new drugs and treatments.
2. Used in Chemical Research:
Ipalbidine serves as a valuable subject for chemical research, particularly in the study of indolizine alkaloids and their potential applications in various fields.
3. Used in Organic Chemistry:
Ipalbidine can be utilized as a starting material or intermediate in the synthesis of other organic compounds, contributing to the advancement of organic chemistry.
4. Used in Crystallography:
The formation of colorless crystals and crystalline salts by ipalbidine makes it an interesting subject for crystallographic studies, which can provide insights into the structural properties of similar compounds.
5. Used in Spectroscopy:
The spectroscopic data obtained from ipalbidine can be used to improve the understanding of the structure and properties of indolizine alkaloids, as well as to develop new techniques and methods in spectroscopy.

References

Gourley et al., Chem. Commun., 709 (1969)

InChI:InChI=1/C15H19NO/c1-11-9-13-3-2-8-16(13)10-15(11)12-4-6-14(17)7-5-12/h4-7,13,17H,2-3,8-10H2,1H3

Upstream product

• 29079-30-9 6-(4-methoxyphenyl)-7-methyl-1,2,3,5,8,8a-hexahydroindolizine 
• 111752-02-4 6-(4'-acetoxyphenyl)-1,2,3,5,6,7,8,8a-octahydro-7-methylindolizin-7-yl acetate 
• 104267-39-2 6-(4-methoxyphenyl)-7-methyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one 
• 220312-30-1 2-(4-Methoxy-phenyl)-1-[2-((E)-3-phenylsulfanyl-allyl)-pyrrolidin-1-yl]-ethanone 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 111751-82-7 2-(4'-acetoxyphenyl)-3-(pyrrol-1-yl)propionic acid 
• 111751-87-2 6-(4'-acetoxyphenyl)-5,6-dihydro-7(8H)-indolizinone 
• 111751-83-8 3-(4'-acetoxyphenyl)-1-diazo-4-(pyrrol-1-yl)-2-butanone 
• 71294-64-9 norhygrine 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 170491-63-1 N-Boc-prolinol 
• 136235-11-5 (S)-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-pyrrolidinecarboxylic acid,1,1-dimethylethyl ester 
• 15761-39-4 N-tert-butoxycarbonyl-proline 

Relevant academic research and scientific papers

Superacid-promoted synthesis of indolizidine derivatives

A series of amido-acetals were reacted with the Br?nsted superacid, CF3SO3H, to provides indolizidine derives by a cyclization cascade. A mechanism is proposed involving formation of a vinylogous enol which undergoes a 6π-electrocycl

Synthesis of (+)-Ipalbidine Based on 6-exo-trig Radical Cyclization of a β-Amino Radical

N-Boc (S)-proline was converted into (2S)-2-[(phenylselanyl)methyl]pyrrolidine, which was alkylated on nitrogen with 2-bromo-1-(4-methoxyphenyl)ethan-1-one. Reaction with vinyllithium, 6-exo-trig radical cyclization (Bu3SnH, AIBN, PhMe, 110 °C), dehydration (P2O5, H3PO4), and demethylation (BBr3) gave (+)-ipalbidine with ee >99%.

A synthesis of (±)-ipalbidine using sulfur-controlled 6-exo selective radical cyclization of α-phenylthio amide

A synthesis of (±)-ipalbidine (1) has been achieved using Bu3SnH- mediated 6-exo selective radical cyclization of 2-[3-(phenylthio)prop-2- enyl]-N-[α(p-methoxyphenyl)-α-(phenylthio)acetyl]pyrrolidine (15) as a key step.

Intramolecular Carbenoid Reactions of Pyrrole Derivatives. A Total Synthesis of (+/-)-Ipalbidine

A mew method for alkaloid synthesis is described.The rhodium(II)-acetate-catalyzed decomposition of 3-(4-acetoxyphenyl)-1-diazo-4-(pyrrol-1-yl)-2-butanone (5d) gave 6-(4-acetoxyphenyl)-5,6-dihydro-7(8H)-indolizinone (6d) in 82percent yield via an intramolecular carbenoid reaction.The latter compound was converted in four steps in 13percent overall yield to (+/-)-ipalbidine (1b).

A Concise Total Synthesis of (+/-)-Ipalbidine by Application of the Aldimine-Diene Cyclocondensation Reaction

The scope of the diene-imine cyclocondensation reaction has been extended to the unstable Δ1-pyrroline.Cyclocondensation of this compound with the silylketene acetal derived from ethyl 2-p-anisyl-3-methylcrotonate provides the basis for a rapid

SYNTHESIS OF THE ALKALOIDS JULANDINE AND IPALBIDINE - USE OF SILICON (IV) CHLORIDE

Titanium (IV) chloride and silicon (IV) chloride with high oxygen affinity are the best Lewis acid catalysts, of a number tested, for cyclisation of an enamine-ketone (1) leading to the alkaloid, julandine (2); cyclisation of (6) in methanol solution without catalyst yields O-methylipalbidine (7).