Inotilone

Base Information

• Chemical Name: Inotilone
• CAS No.: 906366-79-8
• Molecular Formula: C₁₂H₁₀O₄
• Molecular Weight: 218.209
• European Community (EC) Number: 618-603-8
• UNII: CN7VXC9PKS
• Metabolomics Workbench ID: 118985
• Wikipedia: Inotilone
• Mol file: 906366-79-8.mol

Synonyms:inotilone

Chemical Property of Inotilone

Chemical Property:

• Melting Point: 177.4 °C
• Boiling Point: 491.9±45.0 °C(Predicted)
• PKA: 8.58±0.35(Predicted)
• PSA: 66.76000
• Density: 1.433±0.06 g/cm3(Predicted)
• LogP: 1.94180
• Solubility.: ≤1mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 218.05790880
• Heavy Atom Count: 16
• Complexity: 356

Purity/Quality:

98%min ^*data from raw suppliers

Inotilone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C(=CC2=CC(=C(C=C2)O)O)O1
• Isomeric SMILES: CC1=CC(=O)/C(=C/C2=CC(=C(C=C2)O)O)/O1
• Uses: A potent COX-2 inhibitor. Inotilone is used for treating degenerative conditions from overexpression of iNOS.

Technology Process of Inotilone

There total 9 articles about Inotilone 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: 70.9%

5-methyl-3(2H)-furanone (3511-32-8) + 3,4-dihydroxybenzaldehyde (139-85-5) → inotilone (1284249-40-6,906366-79-8)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; water; at 20 ℃; Reflux;

DOI:10.1080/00397910903047778

Reference yield: 70.0%

5-methyl-3-trimethylsilyloxyfuran (942294-32-8) + 3,4-dihydroxybenzaldehyde (139-85-5) → 2-(2,4-dihydroxybenzylidene)-5-methylfuran-3-one (906366-79-8)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at -30 ℃; for 72h;

DOI:10.1016/j.tetlet.2007.03.166

Reference yield: 20.0%

5-methyl-3(2H)-furanone (3511-32-8) + 2,3-dihydroxybenzaldehyde (24677-78-9) → inotilone (1284249-40-6,906366-79-8)

Guidance literature:

5-methyl-3(2H)-furanone; 2,3-dihydroxybenzaldehyde; With tri-sec-butylborate; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃;

With acetic acid; In dichloromethane; N,N-dimethyl-formamide; at 60 ℃; for 0.5h;

upstream raw materials:

5-methyl-3-trimethylsilyloxyfuran

3,4-dihydroxybenzaldehyde

5-methyl-3(2H)-furanone

1-bromo-2,4-dioxopentane

Refernces

• 1、 Al-Busafi, Saleh,Al-Belushi, Muna,Al-Muqbali, Khalid. "Short synthesis of COX-2 inhibitor inotilone". experimental part. p. 1088 - 1092. Retrieved 2010/05/18.