486-89-5

Basic information

• Product Name: ANAGYRINE
• Synonyms: ANAGYRINE;RHOMBININE;3,4,5,6-Tetradehydrospartein-2-one;7,14-Methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one, 7,7a,8,9,10,11,13,14-octahydro-, [7R-(7alpha,7abeta,14alpha)]-;Anagyrin;Monolupin;Monolupine;Rhombinin
• CAS NO: 486-89-5
• Molecular Formula: C15H20N2O
• Molecular Weight: 244.33
• Product Categories: Alkaloids
• Mol File: 486-89-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: bp4 210-215°; bp12 260-270°
• Flash Point: 216.3°C
• Appearance: /
• Density: 1.22±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.73E-08mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• PKA: 9.71±0.20(Predicted)
• CAS DataBase Reference: ANAGYRINE(CAS DataBase Reference)
• NIST Chemistry Reference: ANAGYRINE(486-89-5)
• EPA Substance Registry System: ANAGYRINE(486-89-5)

Safety Data

• Hazardous Substances Data: 486-89-5(Hazardous Substances Data)

Usage

Description

An amorphous alkaloid isolated from Thermopsis rhombifolia (Watt), Richards, and also present in Lupinus macounii Rydb. The base forms a perchlorate, m.p. 313°C and a picrate, m.p. 253°C. On catalytic hydrogenation it yields the octahydro derivative, b.p. l40°CjO.2 mm which also forms a perchlorate, m.p. 213°C; [α]D - 40.9° (H20).

Uses

Anagyrine is a naturally occuring alkaloid found in Genista vuralli, which displays antimicrobial activity.

References

Manske, Marion., Can. J. Res., 20B, 265 (1942) Manske, Marion., ibid, 21B, 144 (1943)

InChI:InChI=1/C15H20N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h3,5-6,11-13H,1-2,4,7-10H2/t11-,12+,13+/m0/s1

Upstream product

• 34389-12-3 (+/-)-(3c-[2]pyridyl-(9ar)-octahydro-quinolizin-1c-yl)-methanol 
• 183859-36-1 methyl (+/-)-N-(tert-butyloxycarbonyl)piperidin-2-ylacetate 
• 122059-35-2 ethyl (1-benzylpiperidin-2-yl)acetate 
• 53439-74-0 ethyl(+/-)-(1RS,9aSR)-1,2,3,6,7,8,9,9a-octahydro-4-oxo-9aH-quinolizine-1-carboxylate 
• 75928-96-0 (+/-)-(1S,10R)-1-(hydroxymethyl)octahydroquinolizin-4-one 
• 142-08-5 2-Pyridone 
• 109600-96-6 (+/-)-(7at)-7,7a,8,9,10,11,13,14-octahydro-6H-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocinylium; bromide 
• 17948-29-7 (+/-)-methyl (1S,10S)-4-oxooctahydroquinolizine-1-carboxylate 

Downstream Products

• 486-89-5 (+/-)-thermopsine 

Relevant articles and documents

The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular “Inside-Out” Approach

Bisquinolizidine alkaloids are characterized by a chiral bispidine core (3,7-diazabicyclo[3.3.1]nonane) to which combinations of an α,N-fused 2-pyridone, an endo- or exo-α,N-annulated piperidin(on)e, and an exo-allyl substituent are attached. We developed a modular “inside-out” approach that permits access to most members of this class. Its applicability was proven in the asymmetric synthesis of 21 natural bisquinolizidine alkaloids, among them more than ten first enantioselective total syntheses. Key steps are the first successful preparation of both enantiomers of C2-symmetric 2,6-dioxobispidine by desymmetrization of a 2,4,6,8-tetraoxo precursor, the construction of the α,N-fused 2-pyridone by using an enamine-bromoacrylic acid strategy, and the installation of endo- or, optionally, exo-annulated piperidin(on)es.