3-Furancarboxylic acid, tetrahydro-2-oxo-5-phenyl-, methyl ester

Base Information

• Chemical Name: 3-Furancarboxylic acid, tetrahydro-2-oxo-5-phenyl-, methyl ester
• CAS No.: 22984-61-8
• Molecular Formula: C12H12O4
• Molecular Weight: 220.225
• DSSTox Substance ID: DTXSID10453482
• Nikkaji Number: J705.840C
• Mol file: 22984-61-8.mol

Synonyms:22984-61-8;3-Furancarboxylic acid, tetrahydro-2-oxo-5-phenyl-, methyl ester;DTXSID10453482;2-Oxo-5-phenyltetrahydrofuran-3-carboxylic acid methyl ester

Chemical Property of 3-Furancarboxylic acid, tetrahydro-2-oxo-5-phenyl-, methyl ester

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 220.07355886
• Heavy Atom Count: 16
• Complexity: 281

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1CC(OC1=O)C2=CC=CC=C2

Technology Process of 3-Furancarboxylic acid, tetrahydro-2-oxo-5-phenyl-, methyl ester

There total 15 articles about 3-Furancarboxylic acid, tetrahydro-2-oxo-5-phenyl-, methyl ester 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: 87.0%

C12H12O4 → methyl 2-oxo-5-phenyltetrahydrofuran-3-carboxylate (22984-61-8)

Guidance literature:

With ammonium chloride; In dimethyl sulfoxide; at 135 ℃; for 1h; Solvent; Temperature; Time;

DOI:10.1021/ol402252u

Reference yield: 82.0%

dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate (3709-20-4) → methyl 2-oxo-5-phenyltetrahydrofuran-3-carboxylate (22984-61-8)

Guidance literature:

With gallium(III) trichloride; water; In dichloromethane;

DOI:10.1016/j.tetlet.2011.07.001

Reference yield: 79.0%

dimethyl (rel)-(2S,4aR,5S)-5-(4-methoxyphenyl)-7,7-dimethyl-2-phenylhexahydro-4H-[1,2]oxazino[2,3-b][1,2]oxazine-4,4-dicarboxylate → methyl 2-oxo-5-phenyltetrahydrofuran-3-carboxylate (22984-61-8)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 25 ℃; for 24h;

DOI:10.1007/s11172-016-1575-9

upstream raw materials:

styrene

bis(methoxycarbonyl)(phenyliodinio)methanide

monomethyl monopotassium malonate

malonic acid dimethyl ester

Refernces

• 1、 Allegretti,D'Annibale,Trogolo. "Lactonization of olefins mediated by Mn(OAc)3: A sonochemical approach". . p. 10705 - 10714. Retrieved 1993.
• 2、 Grover, Huck K.,Emmett, Michael R.,Kerr, Michael A.. "γ-substituted butanolides from cyclopropane hemimalonates: An expedient synthesis of natural (R)-dodecan-4-olide". . p. 4838 - 4841. Retrieved 2013/10/08.
• 3、 Chagarovskiy, Alexey O.,Ivanova, Olga A.,Rakhmankulov, Eduard R.,Budynina, Ekaterina M.,Trushkov, Igor V.,Melnikov, Mikhail Ya.. "Lewis acid-catalyzed isomerization of 2-arylcyclopropane-1,1- dicarboxylates: A new efficient route to 2-styrylmalonates". scheme or table. p. 3179 - 3184. Retrieved 2011/02/22.