Lomifylline

Base Information

• Chemical Name: Lomifylline
• CAS No.: 10226-54-7
• Molecular Formula: C13H18 N4 O3
• Molecular Weight: 278.311
• Hs Code.: 2933990090
• European Community (EC) Number: 233-547-0
• UNII: NA91GV8GDJ
• DSSTox Substance ID: DTXSID10144848
• Nikkaji Number: J10.481G
• Wikidata: Q27166504
• NCI Thesaurus Code: C66030
• ChEMBL ID: CHEMBL311948
• Mol file: 10226-54-7.mol

Synonyms:Cervilane;lomifylline

Chemical Property of Lomifylline

Chemical Property:

• Vapor Pressure: 3.97E-11mmHg at 25°C
• Boiling Point: 525.3°Cat760mmHg
• Flash Point: 271.5°C
• PSA: 78.89000
• Density: 1.31g/cm³
• LogP: 0.19300
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 278.13789045
• Heavy Atom Count: 20
• Complexity: 426

Purity/Quality:

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

Lomifylline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CCCCN1C=NC2=C1C(=O)N(C(=O)N2C)C
• Uses: Lomifylline is a methylxanthine analogue which induces Ca2+-release from intracellular stores via the ryanodine receptor.
• Therapeutic Function: Vasodilator

Technology Process of Lomifylline

There total 9 articles about Lomifylline 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: 96.0%

theophylline (58-55-9,75448-53-2) + trimethyl 5-bromoorthopentanoate (87307-20-8) → 7-(5-keto-hexyl)-1,3-dimethylxanthine (10226-54-7)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; at 80 ℃; for 20h;

DOI:10.1021/jacs.1c09587

Reference yield: 94.0%

C13H16N4O2 → 7-(5-keto-hexyl)-1,3-dimethylxanthine (10226-54-7)

Guidance literature:

With methanol; [Co((dimethylglyoximate)BF₂)₂?2H₂O]; at 65 ℃; for 20h; regioselective reaction; Sealed tube; Neutral conditions;

DOI:10.1039/c7cc03919k

Reference yield:

5-Hexen-2-one (109-49-9) → 7-(5-keto-hexyl)-1,3-dimethylxanthine (10226-54-7)

Guidance literature:

Multi-step reaction with 5 steps

1: p-toluenesulfonic acid / benzene / 2 h / Heating

2: 1.) BH₃, 2.) aq. NaOH, H₂O₂ / 1.) THF, RT, 2 h, 2.) THF, 50 deg C

3: pyridine / 18 h / Ambient temperature

4: 1.) K₂CO₃ / 1.) DMF, 120 deg C, 1 h, 2.) DMF, 120 deg C

5: HCl, MeOH / Ambient temperature

With pyridine; hydrogenchloride; methanol; sodium hydroxide; borane; dihydrogen peroxide; potassium carbonate; toluene-4-sulfonic acid; In benzene;

DOI:10.1021/jm980469t

upstream raw materials:

2-(but-3-en-1-yl)-2-methyl-1,3-dioxolane

4-(2-methyl-[1,3]-dioxolan-2-yl)butan-1-ol

5-Hexen-2-one

toluene-4-sulfonic acid 4-(2-methyl-[1,3]dioxolan-2-yl)-butyl ester

Downstream raw materials:

Methylenetriphenylphosphorane

Refernces

• 1、 Hou, Shengtai,Yang, Hongjian,Cheng, Bin,Zhai, Hongbin,Li, Yun. "Cobaloxime-catalyzed hydration of terminal alkynes without acidic promoters". . p. 6926 - 6929. Retrieved 2017/07/10.
• 2、 -. "Use of antibodies to TNF or fragments derived thereof and xanthine derivatives for combination therapy and compositions therefor". . . Retrieved 2008/06/13.