Bicyclo[2.2.2]octane-2,5-dione

Base Information

• Chemical Name: Bicyclo[2.2.2]octane-2,5-dione
• CAS No.: 57346-05-1
• Molecular Formula: C8H10O2
• Molecular Weight: 138.16
• European Community (EC) Number: 637-348-3
• DSSTox Substance ID: DTXSID30544063
• Nikkaji Number: J1.580.582J
• Mol file: 57346-05-1.mol

Synonyms:bicyclo(2.2.2)octane-2,5-dione

Chemical Property of Bicyclo[2.2.2]octane-2,5-dione

Chemical Property:

• Melting Point: 203-205 °C
• Boiling Point: 268.3±33.0 °C(Predicted)
• PSA: 34.14000
• Density: 1.191±0.06 g/cm3(Predicted)
• LogP: 0.94460
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 138.068079557
• Heavy Atom Count: 10
• Complexity: 173

Purity/Quality:

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

Bicyclo[2.2.2]octane-2,5-dione 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CC(=O)C1CC2=O

Technology Process of Bicyclo[2.2.2]octane-2,5-dione

There total 5 articles about Bicyclo[2.2.2]octane-2,5-dione 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: 69.0%

cyclohexenone (930-68-7) + (N-methylanilino)prop-2-enenitrile (69567-06-2) → Bicyclo<2.2.2>octane-2,4-dione (57346-05-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; Mechanism; multistep reaction; other cyclohexenones;

DOI:10.1055/s-1991-26398

Reference yield:

C12H18ClNOSi (1416448-86-6) → Bicyclo<2.2.2>octane-2,4-dione (57346-05-1)

Guidance literature:

With sodiumsulfide nonahydrate; In ethanol; for 10h; Inert atmosphere; Reflux;

Reference yield:

β-Chloroacrylonitrile (871-29-4) + 1-(trimethylsilyloxy)cyclohexa-1,3-diene (61692-22-6) → Bicyclo<2.2.2>octane-2,4-dione (57346-05-1)

Guidance literature:

With sodium hydroxide; 2,6-di-tert-butyl-4-methyl-phenol; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; Yield given. Multistep reaction; 1.) benzene, 70 deg C, 36 h, 2.) CH₂Cl₂, room temperature, 3 days;

DOI:10.1021/jo9601167

upstream raw materials:

cyclohexenone

(N-methylanilino)prop-2-enenitrile

2-acetoxyacrylonitrile

2-(trimethylsiloxy)cyclohexa-1,3-diene

Downstream raw materials:

bicyclo[2.2.2]octa-2,5-diene

endo-5-phenylbicyclo<2.2.2>octan-2-one

exo-5-phenylbicyclo<2.2.2>octan-2-one

5-(ethylenedioxy)-2-phenylbicyclo<2.2.2>octan-2-ol

Refernces

• 1、 Almqvist, Fredrik,Ekman, Niklas,Frejd, Torbjoern. "Synthesis of optically active endo,endo bicyclo[2.2.2]octane-2,5-diol, bicyclo[2.2.2]octane-2,5-dione, and related compounds". . p. 3794 - 3798. Retrieved 2007/10/03.
• 2、 Ahlbrecht,Dietz,Schon,Baumann. "Tandem-Michael addition of 1-cyanoenamines to cyclohexenones. A new access to bicyclo[2.2.2]octanones". . p. 133 - 140. Retrieved 2007/10/02.