Diethyl 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylate

Base Information

• Chemical Name: Diethyl 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylate
• CAS No.: 843-59-4
• Molecular Formula: C14H18 O6
• Molecular Weight: 282.293
• Hs Code.: 2918300090
• European Community (EC) Number: 864-876-3
• NSC Number: 176184
• DSSTox Substance ID: DTXSID10306424
• Nikkaji Number: J3.501.401B
• Mol file: 843-59-4.mol

Synonyms:843-59-4;diethyl 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylate;1,4-diethyl 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylate;DIETHYL-2,5-DIOXOBICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLATE;Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, 2,5-dioxo-, diethyl ester;C14H18O6;diethyl2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylate;NSC176184;Maybridge1_005592;Oprea1_397021;Oprea1_490849;DivK1c_001880;SCHEMBL22397059;HMS557G04;DTXSID10306424;MFCD00213759;AKOS003619995;CCG-247156;NSC-176184;CDS1_000840;AS-69838;CS-0151645;FT-0624821;EN300-51294;A19221;Z57169635;Diethyl 2,5-dioxobicyclo-[2.2.2]octane-1,4-dicarboxylate

Chemical Property of Diethyl 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 111 °C
• Boiling Point: 393.048°C at 760 mmHg
• Flash Point: 173.462°C
• PSA: 86.74000
• Density: 1.321g/cm³
• LogP: 0.81120
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 282.11033829
• Heavy Atom Count: 20
• Complexity: 438

Purity/Quality:

98%min ^*data from raw suppliers

Diethyl 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylate 95.0% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C12CCC(CC1=O)(C(=O)C2)C(=O)OCC

Technology Process of Diethyl 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylate

There total 12 articles about Diethyl 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylate 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: 85.0%

ethylene dibromide (106-93-4) → Diethyl 2,5-Dioxobicyclo<2.2.2>octane-1,4-dicarboxylate (843-59-4)

Guidance literature:

With sodium hydride; at 110 ℃; for 96h;

DOI:10.1021/ja200503j

Reference yield: 82.0%

C20H28O7 (1352816-30-8) → (1S,4S)-2,5-Dioxo-bicyclo[2.2.2]octane-1,4-dicarboxylic acid diethyl ester (843-59-4)

Guidance literature:

With titanium(IV) tetraethanolate; In ethanol; Heating;

DOI:10.1002/anie.201104681

Reference yield: 80.0%

diethyl 1,4-cyclohexanedione-2,5-dicarboxylate (787-07-5) + ethylene dibromide (106-93-4) → Diethyl 2,5-Dioxobicyclo<2.2.2>octane-1,4-dicarboxylate (843-59-4)

Guidance literature:

diethyl 1,4-cyclohexanedione-2,5-dicarboxylate; With sodium hydride; In 1,2-dimethoxyethane; mineral oil; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

ethylene dibromide; In 1,2-dimethoxyethane; mineral oil; Inert atmosphere; Heating;

DOI:10.1021/jm1009956

upstream raw materials:

ethylene dibromide

succinic acid diethyl ester

diethyl 1,4-cyclohexanedione-2,5-dicarboxylate

diethyl malonate

Downstream raw materials:

1,4-bicyclo[2.2.2]octanedicarboxylic acid

C₃₆H₄₈O₇Si

C₃₂H₄₆O₆Si

4-iodobicyclo<2.2.2>octane-1-carboxylic acid

Refernces

• 1、 Le Marquer, Nicolas,Laurent, Mathieu Yves,Martel, Arnaud. "A Practical and Cost-Effective Method for the Synthesis of Bicyclo[22.2]octane-1,4-dicarboxylic Acid". . p. 2185 - 2187. Retrieved 2015/08/03.
• 2、 Moghaddam, Sarvin,Yang, Cheng,Rekharsky, Mikhail,Ko, Young Ho,Kim, Kimoon,Inoue, Yoshihisa,Gilson, Michael K.. "New ultrahigh affinity host-guest complexes of cucurbit[7]uril with bicyclo[2.2.2]octane and adamantane guests: Thermodynamic analysis and evaluation of M2 affinity calculations". supporting information; scheme or table. p. 3570 - 3581. Retrieved 2011/05/04.