Dimethyl 2-oxoglutarate

Base Information

• Chemical Name: Dimethyl 2-oxoglutarate
• CAS No.: 13192-04-6
• Molecular Formula: C7H10O5
• Molecular Weight: 174.153
• Hs Code.: 29183000
• DSSTox Substance ID: DTXSID10157251
• Nikkaji Number: J102.502C
• Wikidata: Q65707091
• ChEMBL ID: CHEMBL4877741
• Mol file: 13192-04-6.mol

Synonyms:dimethyl alpha-ketoglutarate

Chemical Property of Dimethyl 2-oxoglutarate

Chemical Property:

• Appearance/Colour: Slight Yellow Liquid
• Vapor Pressure: 0.023mmHg at 25°C
• Refractive Index: n20/D 1.439(lit.)
• Boiling Point: 249.4 °C at 760 mmHg
• Flash Point: 105 °C
• PSA: 69.67000
• Density: 1.175 g/cm³
• LogP: -0.31830
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 174.05282342
• Heavy Atom Count: 12
• Complexity: 196

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dimethyl2-Ketoglutaconate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC(=O)C(=O)OC
• Uses: Dimethyl 2-oxoglutarate may be used to synthesize the conformationally constrained PNA (peptide nucleic acid) -monomer capable of binding thymine in a triplex motif. It may be used in the synthesis of 4-aryl kainic acid analogs, via highly stereoselective Michael addition reaction with nitrostyrene.

Technology Process of Dimethyl 2-oxoglutarate

There total 16 articles about Dimethyl 2-oxoglutarate 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: 100.0%

methanol (67-56-1) + α-ketoglutaric acid (328-50-7) → dimethyl 2-ketoglutarate (13192-04-6)

Guidance literature:

With boron trifluoride; at 65 ℃; for 0.333333h;

DOI:10.1021/ac049919h

Reference yield: 85.0%

α-ketoglutaric acid (328-50-7) → dimethyl 2-ketoglutarate (13192-04-6)

Guidance literature:

In methanol; benzene; for 0.5h; Ambient temperature;

Reference yield: 76.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + α-ketoglutaric acid (328-50-7) → dimethyl 2-ketoglutarate (13192-04-6)

Guidance literature:

In diethyl ether; at 0 ℃; for 4h;

DOI:10.1021/jo00270a029

upstream raw materials:

2,5-dimethoxy-2,5-dihydro-furan-2-carboxylic acid methyl ester

dimethyl cis-epoxymethylsuccinate

dimethyl trans-epoxymethylsuccinate

diazomethane

Downstream raw materials:

dimethyl (Z)-2-(4-chloro-2-nitrophenylhydrazono)glutarate

dimethyl (E)-2-(4-chloro-2-nitrophenylhydrazono)glutarate

2-[(5-Chloro-2,4-dinitro-phenyl)-hydrazono]-pentanedioic acid dimethyl ester

methyl-γ-methyl-α-(N-benzyloxycarbonyl)-α-dehydroglutamate

Refernces

• 1、 Maeda, Hiroshi,Selvakumar, Natesan,Kraus, George A.. "An efficient synthesis of 4-aryl kainic acid analogs". . p. 943 - 954. Retrieved 1999.
• 2、 Dowd,P.,Kang,K.. "-". . p. 258 - 259. Retrieved 1974.
• 3、 Rajabi, Fatemeh,Wilhelm, Christian,Thiel, Werner R.. "A Br?nsted acidic, ionic liquid containing, heteropolyacid functionalized polysiloxane network as a highly selective catalyst for the esterification of dicarboxylic acids". supporting information. p. 4438 - 4444. Retrieved 2020/08/10.
• 4、 Ferreira De Freitas, Renato,Harding, Rachel J.,Franzoni, Ivan,Ravichandran, Mani,Mann, Mandeep K.,Ouyang, Hui,Lautens, Mark,Santhakumar, Vijayaratnam,Arrowsmith, Cheryl H.,Schapira, Matthieu. "Identification and Structure-Activity Relationship of HDAC6 Zinc-Finger Ubiquitin Binding Domain Inhibitors". supporting information. p. 4517 - 4527. Retrieved 2018/05/31.