Spizofurone

Base Information

• Chemical Name: Spizofurone
• CAS No.: 72492-12-7
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.21
• UNII: 94F21T5G3C
• DSSTox Substance ID: DTXSID20868144
• Nikkaji Number: J20.578H
• Wikidata: Q27271678
• NCI Thesaurus Code: C73190
• Metabolomics Workbench ID: 144609
• ChEMBL ID: CHEMBL18098
• Mol file: 72492-12-7.mol

Synonyms:5-acetylspiro(benzofuran-2(3H)-1'-cyclopropan)-3-one;AG-629;spizofurone

Chemical Property of Spizofurone

Chemical Property:

• Vapor Pressure: 1.73E-06mmHg at 25°C
• Melting Point: 150.0℃~155.0℃
• Refractive Index: 1.5080 (estimate)
• Boiling Point: 396.3 °C at 760 mmHg
• Flash Point: 180.6 °C
• PSA: 43.37000
• Density: 1.33 g/cm³
• LogP: 1.99690
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 202.062994177
• Heavy Atom Count: 15
• Complexity: 330

Purity/Quality:

99% ^*data from raw suppliers

SPIZOFURONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC2=C(C=C1)OC3(C2=O)CC3
• Description: Spizofurone is an antiulcer agent that acts primarily by increasing mucus secretion and microcirculation in gastric mucosa and also by its inhibitory effect on acid secretion.

Technology Process of Spizofurone

There total 8 articles about Spizofurone 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: 88.0%

C13H10O5 (72491-93-1) → 5-acetylspiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (72492-12-7)

Guidance literature:

With sodium chloride; In dimethyl sulfoxide; at 150 ℃; for 1.5h;

DOI:10.1248/cpb.32.3532

Reference yield: 67.0%

methyl 5-acetyl-2-<(tetrahydro-2-oxo-3-furanyl)oxyl>benzoate (80901-29-7) → 5-acetylspiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (72492-12-7) + 5,10'-diacetyl-5',6'-dihydrospirooxocino<3,2-b>benzofuran>-3-one (94243-45-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium chloride; In N,N-dimethyl-formamide; at 150 ℃; for 2h;

DOI:10.1248/cpb.32.3373

Reference yield:

estere metilico dell'acido 5-acetilsalicilico (16475-90-4) → 5-acetylspiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (72492-12-7)

Guidance literature:

Multi-step reaction with 3 steps

2: 55 percent / Et₃N / acetic anhydride / Heating

3: 88 percent / NaCl / dimethylsulfoxide / 1.5 h / 150 °C

With triethylamine; sodium chloride; In acetic anhydride; dimethyl sulfoxide;

DOI:10.1248/cpb.32.3532

upstream raw materials:

α-bromo-γ-butyrolactone

estere metilico dell'acido 5-acetilsalicilico

C₁₃H₁₀O₅

methyl 5-acetyl-2-<(tetrahydro-2-oxo-3-furanyl)oxyl>benzoate

Downstream raw materials:

Toluene-4-sulfonic acid 2-(5-acetyl-benzofuran-2-yl)-ethyl ester

Refernces

• 1、 Kawada,Watanabe,Okamoto,Sugihara,Hirata,Maki,Imada,Sanno. "Spirocyclopropane compounds. III. Synthesis of spiro[benzofuran-2(3H),1'-cyclopropan]-3-ones for evaluation of gastric antisecretory and antiulcer agents". . p. 3532 - 3550. Retrieved 2007/10/02.