alpha-Isolupanine

Base Information

• Chemical Name: alpha-Isolupanine
• CAS No.: 486-87-3
• Molecular Formula: C15H24 N2 O
• Molecular Weight: 248.368
• European Community (EC) Number: 207-644-3
• DSSTox Substance ID: DTXSID50871681
• Nikkaji Number: J365.219J
• Wikidata: Q104169999
• ChEMBL ID: CHEMBL2008918
• Mol file: 486-87-3.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 alpha-Isolupanine

Chemical Property:

• Vapor Pressure: 1.67E-06mmHg at 25°C
• Melting Point: 75-76°
• 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

α-Isolupanin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCN2CC3CC(C2C1)CN4C3CCCC4=O

Technology Process of alpha-Isolupanine

There total 13 articles about alpha-Isolupanine 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: 68.0%

4-chlorobutyl bromide (6940-78-9) + (1S,2R,9S)-11-tert-butoxycarbonyl-7,11-diazatricyclo[7.3.1.02,7]tridecane-6,10-dione → 2-oxo-α-isosparteine (486-87-3)

Guidance literature:

4-chlorobutyl bromide; With iodine; magnesium; In tetrahydrofuran; at 0 ℃; for 3h;

(1S,2R,9S)-11-tert-butoxycarbonyl-7,11-diazatricyclo[7.3.1.0^2,7]tridecane-6,10-dione; In tetrahydrofuran; at -78 ℃; for 1h; Further stages;

DOI:10.1002/anie.201712852

Reference yield:

6-methyl-3,7-diazabicyclo[3.3.1]non-6-en-2-one → 2-oxo-α-isosparteine (486-87-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; dmap / dichloromethane / 20 h

2.1: triethylamine / tetrahydrofuran / 5 h / 20 °C

3.1: Adam’s catalyst; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr

4.1: magnesium; iodine / tetrahydrofuran / 3 h / 0 °C

4.2: 1 h / -78 °C

With dmap; Adam’s catalyst; hydrogen; iodine; magnesium; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/anie.201712852

Reference yield:

3-tert-butoxycarbonyl-6-methyl-3,7-diazabicyclo[3.3.1]non-6-en-2-one → 2-oxo-α-isosparteine (486-87-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / tetrahydrofuran / 5 h / 20 °C

2.1: Adam’s catalyst; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr

3.1: magnesium; iodine / tetrahydrofuran / 3 h / 0 °C

3.2: 1 h / -78 °C

With Adam’s catalyst; hydrogen; iodine; magnesium; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1002/anie.201712852

upstream raw materials:

ethanol

11,12-dehydrolupanine

acetic acid

4-chlorobutyl bromide

Downstream raw materials:

2-(p-tolyl)-2-dehydrosparteine

Refernces

• 1、 Saito, Kazuki,Takamatsu, Satoshi,Sekine, Toshikazu,Ikegami, Fumio,Ohmiya, Shigeru,et al.. "ABSOLUTE CONFIGURATION OF (+)-5,6-DEHYDROLUPANINE, A KEY INTERMEDIATE IN BIOSYNTHESIS OF LUPIN ALKALOIDS". . p. 958 - 959. Retrieved 2007/10/02.
• 2、 Golebiewski, W. Marek,Spenser, Ian D.. "Lactams of sparteine". . p. 716 - 719. Retrieved 2007/10/02.