90-39-1

Basic information

• Product Name: (-)-SPARTEINE
• Synonyms: L-(-)-SPARTEINE;(-)-LUPINIDINE;LUPINIDINE;6β,7α,9α,11α-Pachycarpine;7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine,dodecahydro-, (7S,7aR,14S,14aS)-;(7S,7aα,14α,14aβ)-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine;1-Sparteine;Lupinindin
• CAS NO: 90-39-1
• Molecular Formula: C15H26N2
• Molecular Weight: 234.38
• EINECS: 201-988-8
• Product Categories: Alkaloids;Alkaloids (Others);Biochemistry
• Mol File: 90-39-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 30.5°C
• Boiling Point: 137-138 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.02 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.528(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethanol (Slightly)
• PKA: 2.24, 9.46(at 20℃)
• Water Solubility: 3.04g/L(25 oC)
• Merck: 14,8737
• BRN: 82447
• CAS DataBase Reference: (-)-SPARTEINE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-SPARTEINE(90-39-1)
• EPA Substance Registry System: (-)-SPARTEINE(90-39-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• RIDADR: 3140
• WGK Germany: 3
• RTECS: WG5950000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 90-39-1(Hazardous Substances Data)

Usage

Chemical Properties

Viscous oily liquid; boils around 180°C(356°F); density 1.02 at 20°C (68°F); stronglybasic, a 0.01 M soln. has pH 11.6; slightlysoluble in water (0.3 g/100 mL), dissolvesreadily in alcohol, ether, or chloroform.

Uses

Sparteine occurs in yellow and black lupinbeans (Lupinus luteus L. and L. niger). Italso occurs in other Lupinus species aswell as in Cytisus and Spartium species.Therapeutically, it is used as an oxytocicagent.

Health Hazard

Toxic actions of sparteine are similar to thoseof coniine but are much less toxic than thoseof coniine. The toxic symptoms in mice weretremor, muscle contraction, and respiratorydistress. An intraperitoneal dose lethal toguinea pigs is 23 mg/kg.LD50 value, oral (mice): 220 mg/kg.

InChI:InChI=1/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m1/s1

Upstream product

• 550-90-3 (+)-lupanine 
• 505-18-0 2,3,4,5-tetrahydropyridine 
• 1476-39-7 1,5-diaminopentane dihydrochloride 
• 299-39-8 (-)-sparteine; bis-hydrogen sulfate 
• 2739-98-2 ethyl 2-(pyridinyl-2)acetate 
• 773070-58-9 ethyl {(2S)-1-[(1R)-1-phenylethyl]piperidin-2-yl}acetate 
• 90-39-1 (+-)-sparteine 
• 72074-77-2 d,l-lupanine 
• 489-54-3 (1R,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^2,7.0^10,15]heptadecane-8,16-dione 

Downstream Products

• 489-72-5 (-)-17-oxosparteine 
• 477-22-5 (7S,7'R)-(7at,7'ac',14'at')-Δ^1(14a)-docosahydro-7r,14c;7'r',14'c'-dimethano-[1,6'ξ]bi[dipyrido[1,2-a;1',2'-e][1,5]diazocinyl] 
• 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 
• 489-72-5 (+/-)-(7ac,14at)-dodecahydro-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocin-6-one 
• 2130-67-8 5,6-Didehydrosparteine 
• 489-72-5 17-oxosparteine 
• 486-87-3 (-)-(6S,7R,9R,11R)-lupanine 
• 82263-24-9 (+)-6-benzylsparteine 
• 549503-58-4 2-(2-fluorophenyl)-1-methylethyl diisopropylcarbamate 
• 152857-74-4 (R)-(+)-[1-Benzyl-3-(N,N-dibenzylamino)-propyl] 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 

Relevant articles and documents

ALKALOID DISTRIBUTION IN SOME SPECIES OF THE PAPILIONACEOUS TRIBES SOPHOREAE, DALBERGIEAE, LOTEAE, BRONGNIARTIEAE AND BOSSIAEEAE

Quinolizidine and dipiperidine alkaloid profiles have been determined for various plant parts of ten papilionaceous species in the tribes Sophoreae, Dalbergieae, Brongniartieae and Bossiaeeae.Alkaloids have been identified for the first time from species in the tribes Dalbergieae (Dalbergia monetaria) and Brongniartieae (Harpalyce formosa var. formosa) of Polhill's classification system of the Papilionoideae.No alkaloids were detected in seeds of several Lotus species (tribe Loteae).Quinolizidine-indolizidine alkaloids of the leontidine type, including 11-epileontidane, a new compound, were obtained from the leaves and stems of Maackia amurensis. 11,12-Dehydrosparteine, a compound which has not previously been characterized as a natural product, was observed in an extract of the stems of Templetonia egena. - Key Word Index - Papilionoideae; tribes Sophoreae, Dalbergieae, Loteae, Brongniartieae, Bossiaeeae; Leguminosae; chemotaxonomy; quinolizidine alkaloids; 11-epileontidane; 11,12-dehydrosparteine.

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.

PROCESS FOR CONVERTING LUPANINE INTO SPARTEINE

The present invention relates to processes for preparing enantiopure Lupanine and Sparteine.