1143-54-0

Basic information

• Product Name: deoxynupharidine
• Synonyms: deoxynupharidine;(1R)-1α,7β-Dimethyl-4β-(3-furanyl)-1,3,4,6,7,8,9,9aα-octahydro-2H-quinolizine;(1R,9aα)-1α,7β-Dimethyl-4β-(3-furanyl)octahydro-2H-quinolizine;[1R,(-)]-1,3,4,6,7,8,9,9aα-Octahydro-4β-(3-furyl)-1,7β-dimethyl-2H-quinolizine;Desoxynupharidine
• CAS NO: 1143-54-0
• Molecular Formula: C15H23NO
• Molecular Weight: 233.34922
• Mol File: 1143-54-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 308.3°Cat760mmHg
• Flash Point: 140.3°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 0.000685mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: deoxynupharidine(CAS DataBase Reference)
• NIST Chemistry Reference: deoxynupharidine(1143-54-0)
• EPA Substance Registry System: deoxynupharidine(1143-54-0)

Safety Data

• Hazardous Substances Data: 1143-54-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H23NO/c1-11-3-5-14-12(2)4-6-15(16(14)9-11)13-7-8-17-10-13/h7-8,10-12,14-15H,3-6,9H2,1-2H3/t11-,12+,14-,15-/m0/s1

Upstream product

• 32486-93-4 6-dehydrodeoxynupharidine 
• 62740-41-4 3-(5-methyl-2-pyridyl)butan-2-one ethylene acetal 
• 62740-46-9 3-(5-methyl-2-pyridyl)butan-2-one 
• 18113-81-0 2-ethyl-5-methylpyridine 
• 96791-40-1 (R)-1,7-Dimethyl-1,2,3,8,9,9a-hexahydro-quinolizin-4-one 
• 62724-10-1 1,7-dimethyl-4-(3-furyl)quinolizidin-2-one 
• 468-89-3 nupharidine 
• 616866-58-1 (R)-4-[(S)-5-methylene-1-(toluene-4-sulfonyl)piperidin-2-yl]pent-2-enoic acid ethyl ester 
• 616866-56-9 N-{1-[2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-4-(hydroxymethyl)pent-4-enyl}-4-methylbenzenesulfonamide 
• 616866-52-5 2(S)-[2-(tert-butyl-dimethyl-silanyloxy)-1(S)-methyl-ethyl]-5-methylene-1-(toluene-4-sulfonyl)-piperidine 
• 616866-50-3 2(S)-[2-(tert-butyl-dimethyl-silanyloxy)-1(S)-methyl-ethyl]-N-(p-toluenesulfonyl)-aziridine 
• 616866-65-0 (S)-2-[(S)-5-methylene-1-(toluene-4-sulfonyl)piperidin-2-yl]propan-1-ol 
• 616866-46-7 (2R,3S)-N-(p-toluenesulfonyl)-3-methylaspartic acid dimethyl ester 
• 616866-48-9 (1R,2S)-N-(3-hydroxy-1-hydroxymethyl-2-methyl-propyl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Stereoselective synthesis of Nuphar quinolizidine alkaloid, (-)-deoxynupharidine

A stereoselective synthetic route to Nuphar quinolizidine alkaloid, (-)-deoxynupharidine, was established by employing reductive carbon-nitrogen bond cleavage, followed by simultaneous recyclization of a proline derivative with samarium diiodide, and an intramolecular ring-closing metathesis, as the key steps.

Novel chiral synthetic path to indolizidine and quinolizidine alkaloids by means of a samarium diiodide-promoted reductive carbon-nitrogen cleavage reaction: Synthesis of (+)-(8R, 8aR)-perhydro-8-indolizidinol and (-)-deoxynupharidine

Novel chiral synthetic procedures for indolizidine and quinolizidine alkaloids were developed, where a samarium diiodide-promoted carbon-nitrogen bond cleavage reaction was employed as a key step. Application of the procedure led to the total synthesis of (+)-(8R, 8aR)-perhydro-8-indolizidinol and (-)-deoxynupharidine.

Diels-Alder Reaction of 1-Azadienes. A Total Synthesis of Deoxynupharidine

The Diels-Alder reaction of a N-acyl-1-azadiene was a key step in the total synthesis of the quinolizidine alkaloid (-)-deoxynupharidine.