Naxifylline

Base Information

• Chemical Name: Naxifylline
• CAS No.: 166374-49-8
• Molecular Formula: C₁₈H₂₄N₄O₃
• Molecular Weight: 344.414
• UNII: B3G45WC37L
• Wikidata: Q27274317
• NCI Thesaurus Code: C83991
• ChEMBL ID: CHEMBL3989819
• Mol file: 166374-49-8.mol

Synonyms:1,3-dipropyl-8-(2-(5,6-epoxy)norbornyl)xanthine;1,3-ENX;Adentri;BG 9719;BG-9719;BG9719;CVT 124;CVT-124;ENX cpd

Chemical Property of Naxifylline

Chemical Property:

• Vapor Pressure: 3.57E-14mmHg at 25°C
• Boiling Point: 596.1°C at 760 mmHg
• Flash Point: 314.3°C
• Density: 1.32g/cm³
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 344.18484064
• Heavy Atom Count: 25
• Complexity: 599

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCN1C2=C(C(=O)N(C1=O)CCC)NC(=N2)C3CC4CC3C5C4O5
• Isomeric SMILES: CCCN1C2=C(C(=O)N(C1=O)CCC)NC(=N2)[C@H]3C[C@H]4C[C@@H]3[C@H]5[C@@H]4O5

Technology Process of Naxifylline

There total 13 articles about Naxifylline 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: 66.0%

8-<(1S,2S)-5-Norbornen-2-yl>-1,3-dipropylxanthine (190316-05-3) → 1,3-dipropyl-8-[5,6-exo-epoxy-(1S,2S)-norbornan-2-yl]xanthine (190316-06-4,166374-48-7,166374-49-8)

Guidance literature:

With magnesium monoperoxyphthalate hexahydrate; In water; isopropyl alcohol; for 20h; Ambient temperature;

DOI:10.1021/jm970013w

Reference yield: 58.3%

1,3-dipropyl-8-((1R,2R)-5-norbornen-2-yl)xanthine (190316-03-1) → CVT-124 (166374-48-7,166374-49-8)

Guidance literature:

With magnesium monoperoxyphthalate hexahydrate; In water; isopropyl alcohol; for 20h; Ambient temperature;

DOI:10.1021/jm970013w

Reference yield:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) → 1,3-dipropyl-8-[5,6-exo-epoxy-(1S,2S)-norbornan-2-yl]xanthine (190316-06-4,166374-48-7,166374-49-8)

Guidance literature:

Multi-step reaction with 5 steps

1: oxalyl chloride / CH₂Cl₂ / 2 h / 20 °C

2: 14.5 g / Et₃N / tetrahydrofuran / 20 °C

3: 43 percent / aq. NaOH / methanol / 15 h / Heating

4: 44 percent / peracetic acid / CH₂Cl₂ / 16 h / 20 °C

5: tetrahydrofuran / 6 h / 45 - 50 °C / Irradiation

With peracetic acid; sodium hydroxide; oxalyl dichloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1081/SCC-120021980

upstream raw materials:

1,3-dipropyl-8-((1R,2R)-5-norbornen-2-yl)xanthine

5-norbornene-2-carboxylic acid

(1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester

5-norbornene-endo-2-carbonyl chloride

Refernces

• 1、 Pfister, Jürg R.,Belardinelli, Luiz,Lee, Gavin,Lum, Robert T.,Milner, Peter,Stanley, William C.,Linden, Joel,Baker, Stephen P.,Schreiner, George. "Synthesis and biological evaluation of the enantiomers of the potent and selective A1-adenosine antagonist 1,3-dipropyl-8-[2-(5,6-epoxynorbonyl)]- xanthine". . p. 1773 - 1778. Retrieved 2007/10/03.