Protoanemonin

Base Information

• Chemical Name: Protoanemonin
• CAS No.: 108-28-1
• Molecular Formula: C5H4O2
• Molecular Weight: 96.0856
• Hs Code.: 2932209090
• European Community (EC) Number: 203-567-4
• UNII: 66FQZ1A5SO
• DSSTox Substance ID: DTXSID10148346
• Nikkaji Number: J10.112E
• Wikipedia: Protoanemonin
• Wikidata: Q421294
• Metabolomics Workbench ID: 51888
• Mol file: 108-28-1.mol

Synonyms:5-methylene-2(5H)-furanone;5-methylene-2-furanone;protoanemonin

Chemical Property of Protoanemonin

Chemical Property:

• Vapor Pressure: 0.122mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: 1.492
• Boiling Point: 219 °C at 760 mmHg
• Flash Point: 81.5 °C
• PSA: 26.30000
• Density: 1.14g/cm³
• LogP: 0.61310
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 96.021129366
• Heavy Atom Count: 7
• Complexity: 144

Purity/Quality:

≥95% ^*data from raw suppliers

5-Methylene-2(5H)-furanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1C=CC(=O)O1

Technology Process of Protoanemonin

There total 50 articles about Protoanemonin 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: 82.0%

5-hydroxy-5-methyl-2(5H)-furanone (14300-71-1) → protoanemonin (108-28-1)

Guidance literature:

With trifluoroacetic acid; In chloroform; at 10 - 15 ℃; for 2h;

Reference yield: 80.0%

3,5-di-O-p-toluoyl-2-deoxy-D-ribono-1,4-lactone (53009-05-5) → protoanemonin (108-28-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1081/SCC-120025181

Reference yield: 60.0%

γ-hydroxymethyl-α,β-butenolide (10374-60-4) → protoanemonin (108-28-1)

Guidance literature:

With sodium acetate; Heating;

upstream raw materials:

5-(acetyloxy)-5-methyl-2(5H)-furanone

pent-2t-en-4-ynoic acid

4-oxo-2-pentenoic acid

2-methylfuran

Downstream raw materials:

valeric acid

3,3'-bis(p-tolyl)-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]

2,5-dihydro-3'-(p-tolyl)spiroisoxazolino-[5',5]furan-2-one

3,3'-diphenyl-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]

Refernces

• 1、 Iovel, Irina,Goldberg, Yuri,Shymanska, Mariya. "A Novel Synthesis of Protoanemonin by the Catalytic Vapour-phase Oxidation of Silvan". . p. 1079 - 1080. Retrieved 1990.
• 2、 Crey, Caroline,Dumy, Pascal,Lhomme, Jean,Kotera, Mitsuharu. "A Convenient Synthesis of Protoanemonin". . p. 3727 - 3732. Retrieved 2003.
• 3、 Tsuboi, Sadao,Wada, Hiroshi,Mimura, Shigetoshi,Takeda, Akira. "A Facile Synthesis of γ-Alkylidene-α,β-unsaturated γ-Lactones". . p. 937 - 938. Retrieved 1987.
• 4、 HILL,VAN HEYNINGEN. "Ranunculin; the precursor of the vesicant substance of the buttercup.". . p. 332 - 335. Retrieved 1951.
• 5、 Munoz, Alberto,Murelli, Ryan P.. "Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: Synthesis of a new class of spirocyclic ketal-lactones". . p. 6779 - 6781,3. Retrieved 2012.
• 6、 Roupioz, Yoann,Lhomme, Jean,Kotera, Mitsuharu. "Chemistry of the 2-deoxyribonolactone lesion in oligonucleotides: Cleavage kinetics and products analysis". . p. 9129 - 9135. Retrieved 2002.
• 7、 Grundmann,Kober. "-". . p. 2332. Retrieved 1955.
• 8、 -. "Synthetic method for protoanemonin". Paragraph 0039-0040; 0041-0042. . Retrieved 2019/05/15.