Ethyl 2-oxo-4-phenylbutyrate

Base Information

• Chemical Name: Ethyl 2-oxo-4-phenylbutyrate
• CAS No.: 64920-29-2
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• Hs Code.: 2918300090
• European Community (EC) Number: 265-276-9
• UNII: 5YNU9LPT51
• DSSTox Substance ID: DTXSID1057793
• Nikkaji Number: J138.296I
• Wikidata: Q27263064
• ChEMBL ID: CHEMBL3183364
• Mol file: 64920-29-2.mol

Synonyms:2-Oxo-4-phenylbutanoicacid ethyl ester;2-Oxo-4-phenylbutyric acid ethyl ester;4-Phenyl-2-oxobutyricacid ethyl ester;Ethyl 2-oxo-4-phenylbutanoate;Ethyl 3-benzylpyruvate;Ethyl 4-phenyl-2-ketobutyrate;Ethyl4-phenyl-2-oxobutanoate;Ethyl benzylpyruvate;

Chemical Property of Ethyl 2-oxo-4-phenylbutyrate

Chemical Property:

• Appearance/Colour: Pale yellow or yellow liquid
• Vapor Pressure: 0.000657mmHg at 25°C
• Refractive Index: n20/D 1.504(lit.)
• Boiling Point: 309 °C at 760 mmHg
• Flash Point: 140 °C
• PSA: 43.37000
• Density: 1.091 g/cm³
• LogP: 1.75140
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 206.094294304
• Heavy Atom Count: 15
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 2-oxo-4-phenylbutyrate, 90+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=O)CCC1=CC=CC=C1
• Uses: Ethyl 2-oxo-4-phenylbutyrate may be used in the synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate, an important chiral precursor for angiotensin-converting enzyme (ACE) inhibitor.

Technology Process of Ethyl 2-oxo-4-phenylbutyrate

There total 29 articles about Ethyl 2-oxo-4-phenylbutyrate 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: 99.0%

ethyl 2-hydroxy-4-phenylbutanoate (93921-85-8) → 2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; calcium methylate; In acetonitrile; at 0 - 20 ℃;

DOI:10.1080/00397911.2011.584650

Reference yield: 98.0%

(Z)-ethyl 2-oxo-4-phenyl-3-butenoate (55674-14-1) → 2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2)

Guidance literature:

Reference yield: 93.0%

(4-Ethoxybut-3-enyl)benzene → 2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2)

Guidance literature:

With potassium permanganate; sodium hydrogencarbonate; magnesium sulfate; In water; acetone; at 23 ℃; for 0.0833333h;

DOI:10.1021/jo00124a049

upstream raw materials:

2,2-Bis-ethylsulfanyl-4-phenyl-butyric acid ethyl ester

ethanol

dihydrocinnamonitrile

methyl methylsulfinylmethyl sulfide

Downstream raw materials:

ethyl 2-cyano-4-phenyl-2-[(trimethylsilyl)oxy]butanoate

ethyl (R)-2-hydroxy-4-phenylbutyrate

(Z)-2-Methoxycarbonylamino-4-phenyl-but-2-enoic acid ethyl ester

ethyl 2-phenethylpropenoate

Refernces

• 1、 Heuson, Egon,Charmantray, Franck,Petit, Jean-Louis,de Berardinis, Véronique,Gefflaut, Thierry. "Enantioselective Synthesis of d- and l-α-Amino Acids by Enzymatic Transamination Using Glutamine as Smart Amine Donor". supporting information. p. 778 - 785. Retrieved 2019/01/04.
• 2、 Becerra, Diana,Raimondi, Wilfried,Dauzonne, Daniel,Constantieux, Thierry,Bonne, Damien,Rodriguez, Jean. "Enantioselective Organocatalyzed Consecutive Synthesis of Alkyl 4,5-Dihydrofuran-2-carboxylates from α-Keto Esters and (Z)-β-Chloro-β-nitrostyrenes". supporting information. p. 195 - 201. Retrieved 2016/12/24.