Norloline

Base Information

• Chemical Name: Norloline
• CAS No.: 4839-19-4
• Molecular Formula: C7H12N2O
• Molecular Weight: 140.183
• Wikidata: Q105256924
• Mol file: 4839-19-4.mol

Synonyms:Norloline;N-Depropionyldecorticasine;(1S,6R,7R,7aS)-Hexahydro-1H-1,6-epoxypyrrolizin-7-amine;4839-19-4;(1R,3S,7S,8R)-2-oxa-6-azatricyclo[4.2.1.03,7]nonan-8-amine;2,4-Methano-4H-furo(3,2-b)pyrrol-3-amine, hexahydro-, (2R-(2alpha,3alpha,3abeta,4alpha,6abeta))-;CHEBI:156447;AKOS006338916

Chemical Property of Norloline

Chemical Property:

• Vapor Pressure: 0.0926mmHg at 25°C
• Boiling Point: 224.2°Cat760mmHg
• Flash Point: 89.4°C
• Density: 1.3g/cm³
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 140.094963011
• Heavy Atom Count: 10
• Complexity: 173

Purity/Quality:

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

N-Demethylloine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CN2CC3C(C2C1O3)N
• Isomeric SMILES: C1CN2C[C@@H]3[C@@H]([C@H]2[C@H]1O3)N
• Description: A simple amino-pyrrolizidine alkaloid, present in the seeds of Lolium cuneatum, the base is a colourless liquid which is dextrorotatory with [α] 16 D+ 15.1 0. The above structure has been elucidated from spectroscopic data.

Technology Process of Norloline

There total 13 articles about Norloline 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: 90.0%

C7H10N4O (1315552-06-7) → Norlolin (4839-19-4,103531-60-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1038/nchem.1072

Reference yield:

(1S,3S,7R)-2-Oxa-6-aza-tricyclo[4.2.1.03,7]nonane-8-carboxylic acid hydrazide (103478-47-3) → dl-norloline (4839-19-4,103531-60-8)

Guidance literature:

With sodium hydroxide; In methanol; water;

DOI:10.1021/jo00368a035

Reference yield:

(1S,3S,7R)-1-(2-Oxa-6-aza-tricyclo[4.2.1.03,7]non-8-yl)-methanol (103478-45-1) → dl-norloline (4839-19-4,103531-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Jones reagent, 2.) H₂SO₄ / 2.) benzene

2: hydrazine hydrate / Heating

3: 10percent aq. NaOH / H₂O; methanol

With sodium hydroxide; jones reagent; sulfuric acid; hydrazine hydrate; In methanol; water;

DOI:10.1021/jo00368a035

upstream raw materials:

N-acetylnorloline

C₇H₁₁ClN₄O

C₇H₁₀N₄O

(1S,3S,7R)-2-Oxa-6-aza-tricyclo[4.2.1.0^3,7]nonane-8-carboxylic acid hydrazide

Downstream raw materials:

N-Formyl-norlolin