24915-04-6

Basic information

• Product Name: Isosparteine
• Synonyms: (7S,7aβ,14aβ)-Dodecahydro-7α,14α-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine;(7S,7aβ,14S,14aβ)-Dodecahydro-7α,14α-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine;Isosparteine;β-Isosparteine;b-Isosparteine
• CAS NO: 24915-04-6
• Molecular Formula: C₁₅H₂₆N₂
• Molecular Weight: 234.3803
• Mol File: 24915-04-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: bp0.2 100-110°
• Flash Point: 148.3°C
• Appearance: /
• Density: 1.08g/cm³
• CAS DataBase Reference: Isosparteine(CAS DataBase Reference)
• NIST Chemistry Reference: Isosparteine(24915-04-6)
• EPA Substance Registry System: Isosparteine(24915-04-6)

Safety Data

• Hazardous Substances Data: 24915-04-6(Hazardous Substances Data)

Upstream product

• 1476-39-7 1,5-diaminopentane dihydrochloride 
• 72074-77-2 d,l-lupanine 
• 505-18-0 2,3,4,5-tetrahydropyridine 

Downstream Products

• 489-72-5 17-oxosparteine 
• 489-72-5 17-oxosparteine 
• 117634-60-3 17-phenyl-16,17-dehydrosparteinium hydroxide 
• 489-72-5 (+/-)-(7ac,14at)-dodecahydro-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocin-6-one 
• 2130-67-8 (+/-)-(14at)-1,3,4,7,9,10,11,13,14,14a-decahydro-2H,6H-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocine 
• 90-39-1 (-)-sparteine 

Relevant articles and documents

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Oxidative deamination of tetrahydroanabasine with o-quinones: An easy entry to lupinine, sparteine, and anabasine

A mild oxidative deamination reaction of tetrahydroanabasine O-methyloxime 17 is described, making use of an o-quinone that is based on topaquinone (TPQ, 11), the cofactor that is present in copper-containing amine oxidases. In situ ring closure of the oxidation product produced double functionalized quinolizidine 5, containing an enamine functionality with excellent reactivity. From this quinolizidine 5 a variety of biogenetically related lupin alkaloids were prepared: lupinine (7) and aminolupinane (8) via reductive sequences and sparteine (9) via a condensation reaction with dehydropiperidine 1. The configurationally more favorable trans isomers epilupinine (25) and β-isosparteine (10) were formed when more drastic reaction conditions were used for oxime hydrolysis. Anabasine (4) and a new 5-piperidylanabasine derivative 6 were formed by an unexpected acid catalyzed ring transformation reaction, whereby the pyridine ring was formed via oxime-induced aromatization. The stereochemistry of the reaction products and the biogenetic implications are discussed.

Correlation between the stereochemistry of quinolizidine alkaloids and their infrared spectra from 2840-2600 CM-1.

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