Lamprolobine

Base Information

• Chemical Name: Lamprolobine
• CAS No.: 18688-40-9
• Molecular Formula: C₁₅H₂₄N₂O₂
• Molecular Weight: 264.368
• Hs Code.: 2925190090
• DSSTox Substance ID: DTXSID00171946
• Nikkaji Number: J1.076.775J
• Wikidata: Q27107171
• Metabolomics Workbench ID: 67969
• Mol file: 18688-40-9.mol

Synonyms:Lamprolobine;18688-40-9;Lamprolobin;1-[[(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methyl]piperidine-2,6-dione;(1R-cis)-1-((Octahydro-2H-quinolizin-1-yl)methyl)-2,6-piperidinedione;1-(((1R,9aR)-octahydro-2H-quinolizin-1-yl)methyl)piperidine-2,6-dione;2,6-Piperidinedione, 1-((octahydro-2H-quinolizin-1-yl)methyl)-, (1R-cis)-;AC1L3EBU;AC1Q6FAJ;2,6-Piperidinedione, 1-[(octahydro-2H-quinolizin-1-yl)methyl]-, (1R-cis)-;SureCN40596;SCHEMBL40596;CHEBI:6369;DTXSID00171946;AKOS040752400;Q27107171

Chemical Property of Lamprolobine

Chemical Property:

• Vapor Pressure: 3.36E-07mmHg at 25°C
• Boiling Point: 418.1°C at 760 mmHg
• Flash Point: 182.2°C
• PSA: 40.62000
• Density: 1.15g/cm³
• LogP: 1.66580
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 264.183778013
• Heavy Atom Count: 19
• Complexity: 353

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CCCC(C2C1)CN3C(=O)CCCC3=O
• Isomeric SMILES: C1CCN2CCC[C@@H]([C@H]2C1)CN3C(=O)CCCC3=O
• Description: The leaves of Lamprolobium fruticosum yields this alkaloid as a colourless oil, [α]20Do + 29° (EtOH) and furnishing a crystalline picrate, m.p. 153-4°C. Acid hydrolysis of the alkaloid yields glutaric acid and (+ )-l-aminoethylquinolizidine. The stereochemistry of the latter has been established by demonstrating the identity of the N-acetyl derivative, m.p. l44-5°C; [α]20Do + 46° (EtOH) with that prepared from epilupinine. The structure has been confirmed from the infrared, NMR and mass spectra. The total synthesis of the optically inactive alkaloid and its epimer has been carried out.

Technology Process of Lamprolobine

There total 19 articles about Lamprolobine 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:

piperidine-2-thione (13070-01-4) → (+/-)-lamprolobine (18688-40-9,22142-02-5,29944-17-0,31679-48-8,56805-12-0,80374-24-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / NaH / tetrahydrofuran / 44.5 h / 50 - 54 °C

2: 2) Et₃N, PPh₃ / 1) r.t., 4 h, 2) CH₂Cl₂, r.t., 165 min

3: 74 percent / LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 3 h, 2) r.t., 62 h

5: 43 percent / NaBH₃CN, conc.HCl / ethanol / 1.33 h / Ambient temperature; pH 4

6: 55 percent / NaH / benzene / 150 h / Heating

7: 84 percent / 3 M aq.NaOH, Ni-Al / aq. ethanol / 94 h / Ambient temperature

8: 2) Ac₂O, NaOAc / 1) Et₂O, 32 min, 2) 120 deg C, 40 min

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; aluminum nickel; sodium acetate; acetic anhydride; sodium hydride; sodium cyanoborohydride; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; benzene;

DOI:10.1016/S0040-4020(01)89049-9

Reference yield:

1-(2-ethoxycarbonylethyl)piperidine-2-thione (58576-26-4) → (+/-)-lamprolobine (18688-40-9,22142-02-5,29944-17-0,31679-48-8,56805-12-0,80374-24-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 2) Et₃N, PPh₃ / 1) r.t., 4 h, 2) CH₂Cl₂, r.t., 165 min

2: 74 percent / LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 3 h, 2) r.t., 62 h

4: 43 percent / NaBH₃CN, conc.HCl / ethanol / 1.33 h / Ambient temperature; pH 4

5: 55 percent / NaH / benzene / 150 h / Heating

6: 84 percent / 3 M aq.NaOH, Ni-Al / aq. ethanol / 94 h / Ambient temperature

7: 2) Ac₂O, NaOAc / 1) Et₂O, 32 min, 2) 120 deg C, 40 min

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; aluminum nickel; sodium acetate; acetic anhydride; sodium hydride; sodium cyanoborohydride; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; benzene;

DOI:10.1016/S0040-4020(01)89049-9

Reference yield:

1-azabicyclo<4.4.0>dec-5-ene-5-carbonitrile (145801-19-0) → (+/-)-lamprolobine (18688-40-9,22142-02-5,29944-17-0,31679-48-8,56805-12-0,80374-24-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 43 percent / NaBH₃CN, conc.HCl / ethanol / 1.33 h / Ambient temperature; pH 4

2: 55 percent / NaH / benzene / 150 h / Heating

3: 84 percent / 3 M aq.NaOH, Ni-Al / aq. ethanol / 94 h / Ambient temperature

4: 2) Ac₂O, NaOAc / 1) Et₂O, 32 min, 2) 120 deg C, 40 min

With hydrogenchloride; sodium hydroxide; aluminum nickel; sodium acetate; acetic anhydride; sodium hydride; sodium cyanoborohydride; In ethanol; benzene;

DOI:10.1016/S0040-4020(01)89049-9

upstream raw materials:

glutaric anhydride,

(±)-aminolupinane

piperidine-2-thione

1-(2-ethoxycarbonylethyl)piperidine-2-thione

Refernces

• 1、 Michael,Jungmann. "New syntheses of (±)-lamprolobine and (±)-epilamprolobine". . p. 10211 - 10220. Retrieved 2007/10/02.