1004-98-4

Basic information

• Product Name: 2,5-Diazabicyclo[2.2.2]octane-3,6-dione
• Synonyms: 2,5-Diazabicyclo[2.2.2]octane-3,6-dione
• CAS NO: 1004-98-4
• Molecular Formula: C₆H₈N₂O₂
• Molecular Weight: 140.13992
• Mol File: 1004-98-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 272-273 °C
• Boiling Point: 554.9±43.0 °C(Predicted)
• Appearance: /
• Density: 1.297±0.06 g/cm3(Predicted)
• PKA: 12.93±0.20(Predicted)
• CAS DataBase Reference: 2,5-Diazabicyclo[2.2.2]octane-3,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diazabicyclo[2.2.2]octane-3,6-dione(1004-98-4)
• EPA Substance Registry System: 2,5-Diazabicyclo[2.2.2]octane-3,6-dione(1004-98-4)

Safety Data

• Hazardous Substances Data: 1004-98-4(Hazardous Substances Data)

Usage

Uses

2,5-Diazabicyclo[2.2.2]octane-3,6-dione can be used to treat medical disorders.

Upstream product

• 54221-37-3 diethyl meso-2,5-dibromoadipate 
• 54221-38-4 (2R,5S)-2,5-diazidohexanedioic acid diethyl ester 
• 84245-58-9 2-Benzyloxycarbonylamino-N-((S)-2-oxo-tetrahydro-furan-3-yl)-malonamic acid tert-butyl ester 
• 84245-59-0 (S)-5-(2-Hydroxy-ethyl)-3,6-dioxo-piperazine-2-carboxylic acid tert-butyl ester 
• 869-10-3 diethyl 2,5-dibromoadipate 
• 915976-48-6 ethyl 5-amino-6-oxopiperidine-2-carboxylate 
• 1069-28-9 dimethyl 2,5-diaminohexanedioate dihydrochloride 
• 84245-60-3 (1S,4S)-3,6-Dioxo-2,5-diaza-bicyclo[2.2.2]octane-1-carboxylic acid tert-butyl ester 
• 52321-01-4 diethyl 2,5-diphthalimidoadipate 

Downstream Products

• 658-24-2 2,5-diazabicyclo[2.2.2]octane 
• 1076206-57-9 2-[(2,3,5-trifluorophenyl)methyl]-2,5-diazabicyclo[2.2.2]octane 
• 42155-72-6 (2R,5R)-5-Amino-6-oxo-piperidine-2-carboxylic acid 
• 84278-06-8 LL-3-amino-2-piperidone-6-carboxylic acid (LL-Acp) 
• 183318-41-4 (2S,5S)-6-Oxo-5-phenylacetylamino-piperidine-2-carboxylic acid methyl ester 
• 183318-47-0 N-((3S,6S)-6-Fluoromethyl-2-oxo-piperidin-3-yl)-2-phenyl-acetamide 
• 213686-08-9 (2S,5S)-2,5-Diamino-hexanedioic acid; hydrochloride 
• 160320-09-2 2,5-Bis-(4-methoxy-benzyl)-2,5-diaza-bicyclo[2.2.2]octane-3,6-dione 

Relevant articles and documents

ALPHA-UNSUBSTITUTED ARYLMETHYL PIPERAZINE PYRAZOLO[1,5-A] PYRIMIDINE AMIDE DERIVATIVES

Methods of preventing, treating or delaying the onset of HIV in a subject by administering to the subject novel pharmaceutically active arylmethyl pyrazolo[1,5-α ]pyrimidine amide derivatives, or pharmaceutical compositions containing the same are described. Additionally, compounds of novel pharmaceutically active arylmethyl piperazine pyrazolo[l,5-α]pyrimidine amide derivatives and their use for the manufacture of specific medicaments are described.

Lithiation of Bridgehead Position in 3,6-Bridged Piperazine-2,5-diones

2,5-Dimethyl-2,5-diazabicyclooctane-3,6-dione can be lithiated at the 1,4 (bridgehead) positions with 2 equiv. of butyllithium at -78 deg C and deuterated with D2O (D0, 11.2; D1, 56.1; D2, 30.1percent).With butyllithium and methyl iodide the 1,2,5-trimethyl and 1,2,4,5-tetramethyl derivatives are obtained.Treatment of dimethyl 2,6-diaminoheptanedioate dihydrochloride with sodium methoxide in boiling butanol gives 6,8-diazabicyclononane-7,9-dione in 62percent yield.N-Methylation of this compound yields 6,8-dimethyl-6,8-diazabicyclononane-7,9-dione which can similarly be lithiated at the 1,5 (bridgehead) positions and deuterated with D2O (D0, 5.6; D1, 70.8; D2, 23.6percent).Lithiation with butyllithium and reaction with methyl iodide, benzyl iodide or bromomethyl methyl ether gives mono- and di-alkylated products at the 1,5-position.The ability to lithiate the bridgehead positions in these compounds is attributed primarily to a combination of the inductive effect of the carbonyl group and dipole stabilization by the amide nitrogen.

Diazabicyclooctanes and diazabicycloheptanes

Twelve analogs of diethylcarbamazine as prepared by acylation of 3- and 8-methyl-3,8-diazabicyclo[3.2.1]octane, 2-methyl-2,5-diazabicyclo[2.2.2]octane, and 2-methyl-2,5-diazabicyclo [2.2.1]heptane with diethylcarbamyl chloride, ethyl chloroformate, ethyl isocyanate, and cyclohexanecarbonyl chloride. These compounds are formally derived from diethylcarbamazine in possessing two- or one-carbon bridges over the piperazine ring. The compounds have utility as antifilarial agents and as bronchodilators.