10252-12-7

Basic information

• Product Name: (12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine
• Synonyms: (12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine
• CAS NO: 10252-12-7
• Molecular Formula: C15H18N2
• Molecular Weight: 226.31682
• Mol File: 10252-12-7.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine(CAS DataBase Reference)
• NIST Chemistry Reference: (12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine(10252-12-7)
• EPA Substance Registry System: (12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine(10252-12-7)

Safety Data

• Hazardous Substances Data: 10252-12-7(Hazardous Substances Data)

Usage

General Description

(12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine, also known as rauwolscine, is a chemical compound found in various plant species, including Rauwolfia serpentina. It is a stereoisomer of yohimbine and belongs to the indole alkaloid class of compounds. Rauwolscine has been studied for its potential medicinal properties, including its role as an alpha-2 adrenergic receptor antagonist, which may contribute to its use as a potential treatment for erectile dysfunction and as a dietary supplement for weight loss and athletic performance enhancement. Its structure and pharmacological activities have made it a subject of interest in drug development and medicinal research.

Upstream product

• 181218-86-0 (S)-1-allyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 4942-85-2 1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-4-one 
• 1444254-58-3 tert-butyl (1S,12bR)-1-acetoxy-4-oxo-1,3, 4 ,6,7,12bhexahydroindolo[2,3-a]quinolizine-12(2H)-carboxylate 
• 1444254-50-5 tert-butyl (S)-3-(2-(3-acetoxy-2,6-dioxopiperidin-1-yl)ethyl)-1H-indole-1-carboxylate 
• 1444254-46-9 tert-butyl (S)-3-(2-(3-hydroxy-2,6-dioxopiperidin-1-yl)ethyl)-1H-indole-1-carboxylate 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 167015-84-1 3-(2-aminoethyl)-indole-1-carboxylic acid tert-butyl ester 
• 1444254-42-5 tert-butyl (S)-3-(2-(5-oxotetrahydrofuran-2-carboxamido)ethyl)-1H-indole-1-carboxylate 
• 1444254-70-9 (1S,12bR)-4-oxo-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]-quinolizin-1-yl phenyl carbonate 
• 1444254-66-3 (-)-(1S,12bR)-1-hydroxy-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one 
• 6067-48-7 1,2,3,4,6,7-Hexahydro-12H-indolo<2.3-a>chinolizinium-chlorid 
• 99545-57-0 (1S)-(+)-2--1-(4-chlorobutyl)-9-methoxymethyl-1,2,3,4-tetrahydro-β-carboline 
• 137119-61-0 (+)-(1R,12bR,SR)-1-<(4-methylphenyl)sulfinyl>-1,2,3,4,6,7,12,12b-octahydro-4-oxoindolo<2,3-a>quinolizine 
• 123642-80-8 (+)-(R)-3,4-dihydro-1-<<(4-methylphenyl)sulfinyl>methyl>-β-carboline 

Relevant articles and documents

Highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to indole natural product synthesis

We report a novel, facile and highly stereoselective approach to the indolo[2,3-a]quinolizine ring system from a readily available, non-racemic chiral template. We demonstrate the potential for application of this methodology to natural product synthesis through conversion of the template to a simple indole alkaloid with high enantiomeric purity.

Enantioselective synthesis of some tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids

Four alkaloids: (R)-(+)-cryspine A 5, (R)-(+)-octahydroindolo[2,3-a]quinolizidine 8, (R)-(+)-harmicine 19 and (R)-(+)-desbromoarborescidine 22 were prepared via the asymmetric transfer hydrogenation reaction of a prochiral enamine (iminium salt). The enan

Enantioselective total synthesis of desbromoarborescidines A-C and the formal synthesis of (S)-deplancheine

Starting from Boc-protected tryptamine and (S)-tetrahydro-5-oxo-2- furancarboxylic acid, facile enantioselective total synthesis of desbromoarborescidines A-C and the formal synthesis of (S)-deplancheine have been accomplished via a common intermediate (S

A highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to natural product synthesis

We present a facile and highly stereoselective approach to the indolo[2,3-a]quinolizine ring system from a readily available, non-racemic chiral template. We demonstrate the potential for application of this methodology to natural product synthesis throug