Eupolauridine

Base Information

• Chemical Name: Eupolauridine
• CAS No.: 58786-39-3
• Molecular Formula: C14H8 N2
• Molecular Weight: 204.23
• UNII: M3LXQ9G7MF
• DSSTox Substance ID: DTXSID80974311
• Nikkaji Number: J13.838J
• Wikidata: Q5851990
• Metabolomics Workbench ID: 44239
• ChEMBL ID: CHEMBL477708
• Mol file: 58786-39-3.mol

Synonyms:eupolauridine;indeno(1,2,3-ij)(2,7)naphthyridine

Chemical Property of Eupolauridine

Chemical Property:

• Vapor Pressure: 3.05E-06mmHg at 25°C
• Melting Point: 153-155 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 399.9°C at 760 mmHg
• PKA: 4.00±0.10(Predicted)
• Flash Point: 181.6°C
• PSA: 25.78000
• Density: 1.375g/cm³
• LogP: 3.27720
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 204.068748264
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=NC=CC4=C3C2=NC=C4
• Description: An uncharacterized alkaloid, canangine has recently been isolated from the bark of Cananga odorata.

Technology Process of Eupolauridine

There total 9 articles about Eupolauridine 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:

4-((E)-2-Dimethylamino-vinyl)-indeno[1,2-b]pyridin-5-one → Indeno<1,2,3ij><2,7>naphthyridine (58786-39-3)

Guidance literature:

With ammonium acetate; In N,N-dimethyl-formamide; at 140 ℃; for 0.5h; Yield given;

DOI:10.1002/ardp.19893220511

Reference yield:

ethyl 2-phenyl-4-methyl-3-pyridinecarboxylate (58787-21-6) → Indeno<1,2,3ij><2,7>naphthyridine (58786-39-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / polyphosphoric acid / 4 h / 130 - 140 °C

2: dimethylformamide / 0.75 h / 120 °C

3: NH₄OAc / dimethylformamide / 0.5 h / 140 °C

With PPA; ammonium acetate; In N,N-dimethyl-formamide;

DOI:10.1002/ardp.19893220511

Reference yield:

onychine (58787-04-5) → Indeno<1,2,3ij><2,7>naphthyridine (58786-39-3)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylformamide / 0.75 h / 120 °C

2: NH₄OAc / dimethylformamide / 0.5 h / 140 °C

With ammonium acetate; In N,N-dimethyl-formamide;

DOI:10.1002/ardp.19893220511

upstream raw materials:

eupolauridine N-oxide

onychine

N,N-dimethylformamide diethyl diacetal

ethyl 3-oxo-3-phenylpropionate

Refernces

• 1、 Waterman, Peter G.,Muhammad, Ilias. "SESQUITERPENES AND ALKALOIDS FROM CLEISTOPHOLIS PATENS". . p. 523 - 528. Retrieved 1985.
• 2、 Bracher, Franz. "Polycyclic Aromatic Alkaloids, II: Synthesis of Onychine and Eupolauridine". . p. 293 - 294. Retrieved 2007/10/02.