DIETHYL 2-ACETYLGLUTARATE

Base Information

• Chemical Name: DIETHYL 2-ACETYLGLUTARATE
• CAS No.: 1501-06-0
• Molecular Formula: C11H18O5
• Molecular Weight: 230.261
• Hs Code.: 2918300090
• European Community (EC) Number: 216-114-0
• NSC Number: 42535
• DSSTox Substance ID: DTXSID301241682
• Nikkaji Number: J26.316H
• Mol file: 1501-06-0.mol

Synonyms:Glutaricacid, 2-acetyl-, diethyl ester (7CI,8CI);Pentanedioic acid, 2-acetyl-, diethylester (9CI);Diethyl 2-acetylglutarate;Diethyl 2-acetylpentanedioate;Diethyl a-acetylglutarate;NSC 42535;

Chemical Property of DIETHYL 2-ACETYLGLUTARATE

Chemical Property:

• Appearance/Colour: Clear colourless to light yellow liquid
• Vapor Pressure: 0.00198mmHg at 25°C
• Refractive Index: n20/D 1.439(lit.)
• Boiling Point: 291.2 °C at 760 mmHg
• Flash Point: 127.5 °C
• PSA: 69.67000
• Density: 1.073 g/cm³
• LogP: 1.09800
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 230.11542367
• Heavy Atom Count: 16
• Complexity: 259

Purity/Quality:

99% ^*data from raw suppliers

Diethylα-Acetylglutarate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CCC(C(=O)C)C(=O)OCC
• Uses: Diethyl α-Acetylglutarate is used in the preparation of furocoumarins as potential HIV-1 integrase inhibitors.

Technology Process of DIETHYL 2-ACETYLGLUTARATE

There total 15 articles about DIETHYL 2-ACETYLGLUTARATE 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: 96.0%

ethyl acetoacetate (141-97-9) + ethyl acrylate (140-88-5,9003-32-1) → diethyl 2-acetylglutarate (1501-06-0)

Guidance literature:

With tetrabutylammomium bromide; triethylamine; In hexane; for 6.33h; Reflux;

Reference yield: 80.0%

ethyl acetoacetate (141-97-9) → diethyl 2-acetylglutarate (1501-06-0)

Guidance literature:

With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In N,N-dimethyl-formamide; at 30 - 45 ℃;

DOI:10.1007/BF00961357

Reference yield:

Ethyl 3-bromopropionate (539-74-2) + ethyl acetoacetate (141-97-9) → diethyl 2-acetylglutarate (1501-06-0)

Guidance literature:

upstream raw materials:

methyl magnesium iodide

diethyl ether

2-acetyl-2-bromo-glutaric acid diethyl ester

ethyl 3-chloropropanoate

Downstream raw materials:

tris-ethyl 3-acetylpentane-1,3,5-tricarboxylate

3-(4-methyl-6-oxo-2-phenyl-1,6-dihydropyrimidin-5-yl)propanoic acid

3-(4-methyl-6-oxo-2-phenyl-1,6-dihydro-pyrimidin-5-yl)-propionic acid ethyl ester

2-Oxoglutaric acid phenylhydrazone

Refernces

• 1、 Vorlaender,Knoetzsch. "-". . p. 317. Retrieved .
• 2、 Banerjee,Das Gupta. "-". . p. 1318,1320. Retrieved 1952.
• 3、 Dong, Wenyue,Yao, Peiyuan,Wang, Yingang,Wu, Qiaqing,Zhu, Dunming. "Chemoenzymatic Stereoselective Synthesis of Substituted γ- or δ-lactams with Two Chiral Centers via Transaminase-catalysed Dynamic Kinetic Resolution". . p. 6311 - 6316. Retrieved 2020/10/15.
• 4、 Sun, Mingna,Hu, Jinfeng,Song, Xiuyun,Wu, Donghui,Kong, Linglei,Sun, Yupeng,Wang, Dongmei,Wang, Yan,Chen, Naihong,Liu, Gang. "Coumarin derivatives protect against ischemic brain injury in rats". . p. 39 - 53. Retrieved 2013/10/01.