38527-73-0

Basic information

• Product Name: 3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione
• Synonyms: 3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione;3-ETHYL-3-(4-NITROPHENYL)-2,6-PIPERIDINEDIONE;nitroglutethimide;2-(p-nitrophenyl)-2-ethylglutarimide;2-ethyl-2-(p-nitrophenyl)-glutarimid;3-ethyl-3-(4-nitrophenyl)-6-piperidinedione;p-nitroglutethimide;3-(4-Nitrophenyl)-3-ethylpiperidine-2,6-dione
• CAS NO: 38527-73-0
• Molecular Formula: C₁₃H₁₄N₂O₄
• Molecular Weight: 262.26126
• EINECS: 253-987-7
• Mol File: 38527-73-0.mol

Chemical Properties

• Boiling Point: 473.3°Cat760mmHg
• Flash Point: 240°C
• Appearance: /
• Density: 1.263g/cm³
• Vapor Pressure: 3.98E-09mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: 3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione(38527-73-0)
• EPA Substance Registry System: 3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione(38527-73-0)

Safety Data

• Hazardous Substances Data: 38527-73-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H14N2O4/c1-2-13(8-7-11(16)14-12(13)17)9-3-5-10(6-4-9)15(18)19/h3-6H,2,7-8H2,1H3,(H,14,16,17)

Upstream product

• 140-29-4 phenylacetonitrile 
• 769-68-6 2-phenylbutanenitrile 
• 74220-50-1 2-ethyl-2-phenylglutarodinitrile 
• 98-95-3 nitrobenzene 
• 6973-78-0 2-(4-Nitrophenyl)-buttersaeureethylester 
• 77-21-4 Glutethimide 
• 192927-32-5 methyl 4-cyano-2-ethyl-2-(4-nitrophenyl)butanoate 
• 24646-25-1 methyl 2-(4-nitrophenyl)butanoate 
• 7463-53-8 2RS-(4-nitrophenyl)butanoic acid 
• 203808-68-8 4-(ethoxycarbonyl)-4-(4'-nitrophenyl)hexanonitrile 

Downstream Products

• 125-84-8 aminoglutethimide 

Relevant articles and documents

An expeditious synthesis of cyclic imides

Trifluoroacetamide was reacted with diacids in the presence of N-ethyl- N-dimethylaminopropylcarbodiimide and of 1-hydroxybenzotriazole to afford cyclic imides of different ring size, providing a single step asymmetric synthesis of thalidomide.

The synthesis of (±)-aminoglutethimide via vicarious nucleophilic aromatic substitution of hydrogen

The synthesis of aminoglutethimide via a one-pot coupling of nitrobenzene, ethyl 2-chlorobutyrate and 3-bromopropionitrile has been achieved via a process involving sequential vicarious nucleophilic aromatic substitution and alkylation.

Resolution of 4-Cyano-4-(4-nitrophenyl)hexanoic acid: Synthesis of (R) and (S)-3-(4-aminophenyl)-3-ethylpiperidine- (aminoglutethimide)

Using (R)- or (S)-1-phenylethylamine as a resolving agent, (R)- and (S)-4-cyano-4-(4-nitrophenyl)hexanoic acids have been isolated. Cyclization of each enantiomer, followed by reduction of the nitro group, afforded (R)- and (S)-aminoglutethimide of high (>99% ee enantiomeric purity, respectively. The absolute configuration of (R)-(+)-3-(4-nitrophenyl)-3-ethylpiperidine-2,6-dione was solved by X-ray single crystal analysis thus establishing the (R)-configuration of the dextrorotatory aminoglutethimide. Attempted resolution of the other precursor of aminoglutethimide, 4-cyano-2-ethyl-(4-nitrophenyl)butanoic acid with (S)-1-phenylethylamine led to the formation of the double salt. Its crystal structure was elucidated by X-ray crystallographic analysis.

Aromatase Inhibitors. Synthesis and Evaluation of Mammary Tumor Inhibiting Activity of 3-Alkylated 3-(4-Aminophenyl)piperidine-2,6-diones

The synthesis and biological evaluation of 3-alkyl-substituted 3-(4-aminophenyl)piperidine-2,6-diones as inhibitors of estrogen biosynthesis are described .In vitro compounds 4-14 showed a stronger inhibition of human placental aromatase compared to aminoglutethimide (AG, compound 3), which recently has become used for the treatment of hormone-dependent breast cancer.The most active derivative, compound 10, showed a 93-fold stronger inhibition than AG.With the exception of 5, 7, and 8, all other compounds exhibited similar or decreased inhibition of bovine adrenal desmolase compared to AG.Compounds 4 and 6-12 showed a stronger inhibition of the plasma estradiol concentration of pregnant mare serum gonadotropin (PMSG) primed Sprague-Dawley (SD) rats compared to the parent compound.Compounds 4, 6-8, 10, and 12 inhibited the testosterone-stimulated tumor growth of ovariectomized 9,10-dimethyl-1,2-benzanthracene (DMBA) tumor-bearing SD rats more strongly than AG.Being stronger and more selective inhibitors of the estrogen biosynthesis than AG, some of the newly developed derivatives of AG might be better candidates for the treatment of the hormone-dependent human breast cancer.