Lupanine

Base Information

• Chemical Name: Lupanine
• CAS No.: 550-90-3
• Molecular Formula: C15H24 N2 O
• Molecular Weight: 248.368
• UNII: 183KU7535A,9K48888N9P
• DSSTox Substance ID: DTXSID001023908
• Nikkaji Number: J10.587B
• Wikidata: Q27103558
• Metabolomics Workbench ID: 51616
• ChEMBL ID: CHEMBL459396
• Mol file: 550-90-3.mol

Synonyms:alpha-isolupanine;lupanine;lupanine monohydrobromide, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer;lupanine monohydrochloride, (7S-(7alpha,7aalpha,14alpha,14aalpha))-isomer;lupanine monohydrochloride, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer;lupanine monoperchlorate, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer;lupanine sulfate (1:1), (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer;lupanine, (7R-(7alpha,7abeta,14alpha,14aalpha))-isomer;lupanine, (7S-(7alpha,7aalpha,14alpha,14aalpha))-isomer;lupanine, (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer

Chemical Property of Lupanine

Chemical Property:

• Vapor Pressure: 1.67E-06mmHg at 25°C
• Melting Point: 40-44°
• Refractive Index: nD24 1.5444
• Boiling Point: 396.7°Cat760mmHg
• PKA: 9.47±0.20(Predicted)
• Flash Point: 172.7°C
• PSA: 23.55000
• Density: 1.16g/cm³
• LogP: 1.74750
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 248.188863393
• Heavy Atom Count: 18
• Complexity: 356

Purity/Quality:

99%, ^*data from raw suppliers

(+)-LupaninePerchlorate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CC3CC(C2C1)CN4C3CCCC4=O
• Isomeric SMILES: C1CCN2C[C@@H]3C[C@H]([C@@H]2C1)CN4[C@@H]3CCCC4=O
• Uses: (+)-Lupanine is used in biological studies with quinolizidine alkaloids in seeds of lupin genotypes of different origins.

Technology Process of Lupanine

There total 25 articles about Lupanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadec-12-en-6-one → (+)-lupanine (550-90-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 2.5h; under 760.051 Torr;

DOI:10.1002/anie.201712852

Reference yield: 30.0%

L-(-)-lupanine D-tartrate salt → (+)-lupanine (550-90-3)

Guidance literature:

With potassium hydroxide; In water;

Reference yield: 19.0%

D-(+)-lupanine-L-tartrate → (+)-lupanine (550-90-3)

Guidance literature:

With potassium hydroxide; In water;

upstream raw materials:

lupanine N⁽¹⁶⁾-oxide

5,6-dehydrolupanine

hydrogen iodide

13α-hydroxylupanine

Downstream raw materials:

17-hydroxylupanine

(+)-17-oxolupanine

(-)-sparteine

(+)-2,17-dioxosparteine

Refernces

• 1、 Saito, Kazuki,Takamatsu, Satoshi,Ohmiya, Shigeru,Otomasu, Hirotaka,Yasuda, Masaho,et al.. "LUPIN ALKALOIDS FROM THE SEEDS OF THERMOPSIS LUPINOIDES". . p. 3715 - 3716. Retrieved 1988.
• 2、 Scharnagel, Dagmar,Goller, Jessica,Deibl, Nicklas,Milius, Wolfgang,Breuning, Matthias. "The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular “Inside-Out” Approach". . p. 2432 - 2435. Retrieved 2018/02/16.
• 3、 -. "Process for preparing enantiopure Lupanine and Sparteine". Paragraph 0033. . Retrieved 2014/12/12.