57346-05-1

Usage

Uses

Used in Organic Synthesis:
Bicyclo[2.2.2]octane-2,5-dione is used as a key intermediate in organic synthesis for its ability to form complex organic molecules. Its highly strained and reactive structure allows for versatile reactions, making it a valuable component in the creation of a wide range of organic compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, Bicyclo[2.2.2]octane-2,5-dione is utilized as a building block for the production of various pharmaceuticals. Its unique structure and reactivity contribute to the development of new and innovative drugs, enhancing the therapeutic potential of medications.
Used in Natural Product Synthesis:
Bicyclo[2.2.2]octane-2,5-dione is employed as a starting material for the synthesis of natural products. Its compatibility with natural product structures and its reactivity make it an essential compound in the field of natural product chemistry, facilitating the production of biologically active compounds with potential applications in medicine and other industries.

Upstream product

• 930-68-7 cyclohexenone 
• 69567-06-2 (N-methylanilino)prop-2-enenitrile 
• 3061-65-2 2-acetoxyacrylonitrile 
• 54781-19-0 2-(trimethylsiloxy)cyclohexa-1,3-diene 
• 871-29-4 β-Chloroacrylonitrile 
• 61692-22-6 1-(trimethylsilyloxy)cyclohexa-1,3-diene 
• 1416448-86-6 C₁₂H₁₈ClNOSi 

Downstream Products

• 130913-07-4 2-phenylbicyclo<2.2.2>oct-2-en-5-one 
• 132267-83-5 endo-2-phenyl<5,5,6,6-²H4>bicyclo<2.2.2>octane 
• 130913-06-3 5-hydroxy-5-phenylbicyclo<2.2.2>octan-2-one 
• 1192365-33-5 5-(ethylenedioxy)-2-phenylbicyclo<2.2.2>octan-2-ol 
• 130913-08-5 exo-5-phenylbicyclo<2.2.2>octan-2-one 
• 130913-08-5 endo-5-phenylbicyclo<2.2.2>octan-2-one 
• 500-23-2 bicyclo[2.2.2]octa-2,5-diene 
• 796966-15-9 (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene 
• 850409-82-4 2,5-bis(3,5-dimethylphenyl)bicyclo[2.2.2]octa-2,5-diene 
• 850409-79-9 2,5-di(2-methylphenyl)bicyclo[2.2.2]octa-2,5-diene 
• 796966-15-9 (1S,4S)-2,5-diphenylbicyclo[2,2,2]octa-2,5-diene 
• 796966-15-9 2,5-diphenylbicyclo[2.2.2]octa-2,5-diene 
• 76478-53-0 1R,4S-(-)-bicyclo<2.2.2>octane-2,5-dione 

Relevant academic research and scientific papers

LOW-MOLECULAR COMPOUND, POLYMER, MATERIAL FOR ELECTRONIC DEVICES, COMPOSITION FOR ELECTRONIC DEVICES, ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC SOLAR CELL ELEMENT, DISPLAY AND LIGHTING EQUIPMENT

A subject for the invention is to provide compounds where a film formation can be made by a wet film formation method, a heating temperature at the film formation is low, the film formed therefrom has high stability, and the other layers can be laminated thereon by a wet film formation method or another method. The compounds are usable as a material for electronic device which decreases little in charge transport efficiency or luminescent efficiency and which have excellent driving stability. The invention resides in a compound and a polymer which are characterized by having a elimination group of a specific structure and in an organic compound characterized by having a elimination group having a low elimination temperature.

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

Optically active C2-symmetric (1S,2S,4S,5S)-bicyclo[2.2.2]octane-2,5-diol ((+)-12; 98% ee) and several selectively protected optically active intermediates useful for synthetic transformations were synthesized via a 1,2-carbonyl transposition route starting from the easily available optically active (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octan-2-one ((-)-2). The synthetic route also allowed the preparation of optically active (1S,4S)-bicyclo[2.2.2]octane-2,5-dione ((+)-14; 98% ee).

Synthesis of bicyclic diones and thiones. Facile methylation of the enolates of bicycloheptane-2,5-dione and bicyclooctane-2,5-dione. An AM1 computational study of bicyclic enolates

A group of bicyclic ketones and thiones have been synthesized for homenolization studies.Bicycloheptane-2,5-dione (6) undergoes unusually rapid tetramethylation giving 3,3,6,6-tetramethylbicycloheptane-2,5-dione (1) in good yield.Treatment of 1 with P2S5 in xylene gave 3,3,6,6-tetramethylbicycloheptane-2,5-dithione (2) and 3,3,6,6-tetramethyl-5-oxo-bicycloheptane-2-thione (3), which was converted into 4 with Raney nickel.Bicyclooctane-2,5-dione (7), prepared via Diels-Alder reaction between 2-trimethylsilyloxy-1,3-cyclohexadiene and α-acetoxyacrylonitrile followed by a one-step desilylation/hydrolysis, also undergoes facile tetramethylation giving 3,3,6,6-tetramethylbicyclooctane-2,5-dione (5) in good yields.AM1 calculations were carried out on the α-enolates of bicycloheptan-2-one, 6, 5-methylidenebicycloheptan-2-one, and 4-acetylbicycloheptan-2-one in an attempt to gain information on the source of the enhanced acidity of the C-3 hydrogens of 6 and 7. Key words: bicyclic ketones, thiones, synthesis.

Tandem-Michael addition of 1-cyanoenamines to cyclohexenones. A new access to bicyclo[2.2.2]octanones

Bicyclo[2.2.2]octane-2,5-diones 5 are easily obtained via tandem Michael addition of 2-(N-methylanilino)acrylonitrile (2) with deprotonated cyclohexenones I. The reaction is highly anti-stereoselective with respect to substituents on C-4 and C-5 of the cyclohexenone and is blocked by disubstitution on C-4. 6-Acylbicyclo[2.2.2]octan-2-ones 25 are obtained by tandem Michael addition of deprotonated 2-(N-methylanilino)but-2-enonitrile (18) with cyclohexenone and subsequent protonation or alkylation. Both reactions gave lower yields or even failed with cyclopentenone and cycloheptenone.