Lupinine

Base Information

• Chemical Name: Lupinine
• CAS No.: 486-70-4
• Molecular Formula: C10H19NO
• Molecular Weight: 169.267
• European Community (EC) Number: 207-638-0,815-126-9
• NSC Number: 21723
• UNII: 33BAJ73U1F,F74RAC8A5Q
• DSSTox Substance ID: DTXSID00197565
• Nikkaji Number: J37.652C
• Wikipedia: Lupinine
• Wikidata: Q412589
• Metabolomics Workbench ID: 51555
• ChEMBL ID: CHEMBL459397
• Mol file: 486-70-4.mol

Synonyms:1S-cis-octahydro-2H-quinolizine-1-methanol;epilupinine;lupinine;lupinine hydrochloride, (1R-trans)-isomer;lupinine, (1S-cis)-isomer;octahydroquinolizine-1-methanol

Chemical Property of Lupinine

Chemical Property:

• Vapor Pressure: 0.000928mmHg at 25°C
• Melting Point: 62-65°C
• Refractive Index: 1.525
• Boiling Point: 245 °C at 760 mmHg
• PKA: 14.90±0.10(Predicted)
• Flash Point: 99.1 °C
• PSA: 23.47000
• Density: 1.04 g/cm³
• LogP: 1.18110
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 169.146664230
• Heavy Atom Count: 12
• Complexity: 149

Purity/Quality:

98%,99%, ^*data from raw suppliers

(-)-Lupinine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-41
• Safety Statements: 22-36/37-39-26

MSDS Files:

Useful:

• Canonical SMILES: C1CCN2CCCC(C2C1)CO
• Isomeric SMILES: C1CCN2CCC[C@H]([C@H]2C1)CO
• Description: This lupin alkaloid was first obtained by Baumert and is present in numerous plants of the Lupinus family, the most important sources being L. luteus, L. niger and L. palmeri Wats. It crystallizes from light petroleum in colourless rhombs and may be boiled without decomposition in a stream of hydrogen. It is laevorotatory with [α]17D - 20.35° (EtOH) and is soluble in H20 and most organic solvents but only sparingly so in petroleum ether. It is a sufficiently strong base to liberate ammonia from its salts. The hydrochloride forms colourless rhombic crystals from aqueous EtOH, m.p. 2l2-3°C; [α]D - 14° (H20); the hydriodide has m.p. 140-1 DC; aurichloride, m.p. 211-3°C; platinichloride as yellow crystals, m.p. 166-166.5°C; (+)-tartrate, m.p. 171°C; [α]D + 15.5° (EtOH); methochloride, m.p. 212-3°C; methiodide, m.p. 295-6°C; phenylurethane, m.p. 98-9°C; (-)-camphorsulphonate, m.p. 184°C; [α]D - 15.3° and the (+)-camphorsulphonate, m.p. 182-3°C; [α]D + 22.5°. The formation of a benzoyl derivative, m.p. 49-S00 C, oxidation of the alkaloid to lupininic acid, C9H16.COOH, m.p. 255°C and dehydration to anhydrolupinine, ClOH17N, a colourless oil of unpleasant odour, b.p. 216-7°C/726 mm all show the presence of a primary alcoholic hydroxyl group. Lupinine does not contain a methylimino group and behaves as a tertiary base. On exhaustive methylation it gives, in three stages, trimethylamine and an unsaturated alcohol. From this, it may be deduced that the alkaloid contains a bicyc1ic system. Several unsuccessful attempts were made to synthesize the alkaloid before this was finally achieved by Clemo and his co-workers. This alkaloid, like the others of the lupinane group, is of little importance in medicine although the p-aminobenzoate has been shown to possess a marked local anaesthetic action. The (+ )-form of the alkaloid has m.p. 68°C; [α]D + 19.9° and yields the (-)- tartrate, m.p.167-8°C; [α]D -15.8°.
• Uses: antifeedant, antiinflammatory, oxytoxic (-)-Lupinine is an alkaloid capable of counteracting ethanol anesthesia. The ι-form of lupinine occurs in seeds andherb of Lupinus luteous L., Chenopodiaceae,and other lupinus species. Its clinical applications are very limited.

Technology Process of Lupinine

There total 79 articles about Lupinine 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: 91.0%

(1R,9aR)-octahydro-1H-quinolizine-1-carboxylic acid (574-99-2) → lupinine (486-70-4)

Guidance literature:

With aluminium hydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1055/s-0030-1258356

Reference yield: 90.0%

(1R)-(9aR)-octahydro-quinolizine-1-carboxylic acid methyl ester (725250-71-5) → lupinine (486-70-4)

Guidance literature:

(1R)-(9aR)-octahydro-quinolizine-1-carboxylic acid methyl ester; With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; for 3h; Inert atmosphere; Reflux;

With Glauber's salt; In tetrahydrofuran; diethyl ether;

DOI:10.1016/j.tet.2011.07.017

Reference yield: 90.0%

(1S,9aR)-Octahydro-1-hydroxymethyl-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine (138713-64-1) → lupinine (486-70-4)

Guidance literature:

With nickel; In ethanol; at 25 ℃; for 10h;

DOI:10.1055/s-1991-26620

upstream raw materials:

lupinine

Ethyl (1R,9aR)-Octahydro-2H-quinolizine-1-carboxylate

(1S,9aR)-Octahydro-1-hydroxymethyl-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine

1,5-diaminopentane dihydrochloride

Downstream raw materials:

phenylurethane of (-)-lupinin

4-nitro-benzoic acid-((9aR)-(9ar)-octahydroquinolizin-1t-ylmethyl ester)

(9aR)-1t-(toluene-4-sulfonyloxymethyl)-(9ar)-octahydro-quinolizin

(+)-epilupinine

Refernces

• 1、 Davies, Stephen G.,Fletcher, Ai M.,Foster, Emma M.,Houlsby, Ian T. T.,Roberts, Paul M.,Schofield, Thomas M.,Thomson, James E.. "An efficient asymmetric synthesis of (-)-lupinine". . p. 8309 - 8311. Retrieved 2014/07/22.
• 2、 Fustero, Santos,Moscardó, Javier,Sánchez-Roselló, María,Flores, Sonia,Guerola, Marta,Pozo, Carlos Del. "Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide". experimental part. p. 7412 - 7417. Retrieved 2011/10/09.