gamma-Fagarine

Base Information

• Chemical Name: gamma-Fagarine
• CAS No.: 524-15-2
• Molecular Formula: C13H11NO3
• Molecular Weight: 229.2313
• Hs Code.: 2934999090
• UNII: GKS8Q870TY
• DSSTox Substance ID: DTXSID20200409
• Nikkaji Number: J6.637K
• Wikidata: Q27108657
• Metabolomics Workbench ID: 44245
• ChEMBL ID: CHEMBL252925
• Mol file: 524-15-2.mol

Synonyms:gamma-fagarine

Chemical Property of gamma-Fagarine

Chemical Property:

• Vapor Pressure: 1.15E-05mmHg at 25°C
• Melting Point: 142°
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 381°Cat760mmHg
• PKA: 6.55±0.40(Predicted)
• Flash Point: 184.2°C
• PSA: 44.49000
• Density: 1.261g/cm³
• LogP: 2.99820
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 229.07389321
• Heavy Atom Count: 17
• Complexity: 273

Purity/Quality:

99%, ^*data from raw suppliers

γ-Fagarine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC2=C1N=C3C(=C2OC)C=CO3
• Uses: Fagarine can be used for its anti-inflammatory constituents. This compound can also be synthesized and evaluated as an anti-HIV-1 agents.

Technology Process of gamma-Fagarine

There total 19 articles about gamma-Fagarine 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%

diazomethane (186581-53-3,908094-01-9,334-88-3) + robustine (2255-50-7) → 4,8-dimethoxyfuro[2,3-b]quinoline (524-15-2)

Guidance literature:

DOI:10.1039/b506944k

Reference yield:

(7S,8R)-4-methoxy-7,8-dihydrofuro[2,3-b]quinoline-7,8-diol (865878-14-4) → 4,8-dimethoxyfuro[2,3-b]quinoline (524-15-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / H₂ / Pd/C

2: 90 percent / acetonitrile

3: 68 percent / NBS / CCl₄

4: 90 percent / NaOMe

5: TFA

With N-Bromosuccinimide; hydrogen; sodium methylate; trifluoroacetic acid; palladium on activated charcoal; In tetrachloromethane; acetonitrile;

DOI:10.1039/b506944k

Reference yield:

(7S,8R)-4-methoxy-5,6,7,8-tetrahydrofuro[2,3-b]quinoline-7,8-diol (865878-22-4) → 4,8-dimethoxyfuro[2,3-b]quinoline (524-15-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / acetonitrile

2: 68 percent / NBS / CCl₄

3: 90 percent / NaOMe

4: TFA

With N-Bromosuccinimide; sodium methylate; trifluoroacetic acid; In tetrachloromethane; acetonitrile;

DOI:10.1039/b506944k

upstream raw materials:

4-chloro-8-methoxy-furo[2,3-b]quinoline

3-chloro-4,8-dimethoxy-furo[2,3-b]quinoline

(2,4,8-trimethoxy-quinolin-3-yl)-acetaldehyde

2,4,8-trimethoxy-3-oxiranyl-quinoline

Refernces

• 1、 Boyd, Derek R.,Sharma, Narain D.,Carroll, Jonathan G.,Loke, Pui L.,O'Dowd, Colin R.,Allen, Christopher C. R.. "Biphenyl dioxygenase-catalysed cis-dihydroxylation of tricyclic azaarenes: Chemoenzymatic synthesis of arene oxide metabolites and furoquinoline alkaloids". . p. 10944 - 10955. Retrieved 2013/09/02.
• 2、 Bhoga, Umadevi,Mali,Adapa, Srinivas R.. "New synthesis of linear furoquinoline alkaloids". . p. 9483 - 9485. Retrieved 2007/10/03.