52065-78-8

Basic information

• Product Name: 2,5-Piperidinedione
• Synonyms: 2,5-Piperidinedione;PIPERIDINE-2,5-DIONE
• CAS NO: 52065-78-8
• Molecular Formula: C₅H₇NO₂
• Molecular Weight: 113.11
• Product Categories: Ketone
• Mol File: 52065-78-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 362.1 °C at 760 mmHg
• Flash Point: 193.6 °C
• Appearance: /
• Density: 1.184 g/cm³
• Vapor Pressure: 1.98E-05mmHg at 25°C
• Refractive Index: 1.47
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.12±0.20(Predicted)
• CAS DataBase Reference: 2,5-Piperidinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Piperidinedione(52065-78-8)
• EPA Substance Registry System: 2,5-Piperidinedione(52065-78-8)

Safety Data

• Hazardous Substances Data: 52065-78-8(Hazardous Substances Data)

Usage

Description

2,5-Piperidinedione, also known as glutarimide or cycloheximide, is an organic compound with the molecular formula C5H7NO2. It is a heterocyclic compound featuring a six-membered piperidine ring with two carbonyl groups at the 2nd and 5th positions. This versatile molecule is widely utilized in various chemical and pharmaceutical applications due to its unique structure and reactivity.

Uses

Used in Pharmaceutical Industry:
2,5-Piperidinedione is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form complex structures with biological targets makes it a valuable building block for the development of new drugs.
Used in Chemical Synthesis:
In the chemical industry, 2,5-Piperidinedione is used as a versatile intermediate for the preparation of a wide range of compounds, including piperidine-dione derivatives. The synthesis process involves several steps, such as lactonization, reduction, azidation, reductive ring expansion, and Dess-Martin Periodinane oxidation, which allow for the creation of diverse chemical entities with potential applications in various fields.
Used in Research and Development:
2,5-Piperidinedione is also employed in research and development for the exploration of new chemical reactions and the discovery of novel compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science. Its unique structure and reactivity make it an attractive candidate for the development of new synthetic methodologies and the creation of innovative molecular architectures.

InChI:InChI=1/C5H7NO2/c7-4-1-2-5(8)6-3-4/h1-3H2,(H,6,8)

Upstream product

• 5154-01-8 2,5-dihydroxypyridine 
• 90292-53-8 5-benzyloxy-N-benzylpyridine-2-one 
• 142-08-5 2-Pyridone 
• 106-60-5 ALA 
• 85-61-0 coenzyme A 
• 79416-27-6 methyl aminolevulinate 
• 617-65-2 Glutamic acid 
• 4344-84-7 5-oxo-tetrahydro-furan-2-carboxylic acid 
• 10374-51-3 5-hydroxymethyl-4,5-dihydrofuranone 
• 19365-07-2 (RS)-5-hydroxypiperidin-2-one 

Downstream Products

• 19365-07-2 (RS)-5-hydroxypiperidin-2-one 
• 5451-09-2 5-aminolevulinic acid hydrochloride 
• 87179-80-4 1-benzyl-5-hydroxypiperidin-2-one 
• 87179-79-1 1-benzyl-5-(benzyloxy)piperidin-2-one 

Relevant articles and documents

Preparation method of 2,5-piperidione

The invention relates to a preparation method of 2,5-piperidione. 2-glutamic acid is used as a starting raw material to perform closed loop reaction to produce a compound 2 under the effects of NaNO2; a compound 3 is produced through borane reduction; a compound 4 is produced under the effects of methylsufonyl chloride; a compound 5 is produced through substitution under the sodium azide effect; a compound 6 is produced through Pd/H2 under the reduction effect; a target compound is generated under the effect of Dess-Martin periodinane. The preparation method has the advantages that the raw materials are cheap and can be easily obtained; the synthetic method is simple; the method belongs to a fire-new method for synthesizing 2,5-piperidione. The method meets the requirements of large-scale industrial production.

A three enzyme pathway for 2-amino-3-hydroxycyclopent-2-enone formation and incorporation in natural product biosynthesis

A number of natural products contain a 2-amino-3-hydroxycyclopent-2-enone five membered ring, termed C5N, which is condensed via an amide linkage to a variety of polyketide-derived polyenoic acid scaffolds. Bacterial genome mining indicates three tandem ORFs that may be involved in C5N formation and subsequent installation in amide linkages. We show that the protein products of three tandem ORFs (ORF33-35) from the ECO-02301 biosynthetic gene cluster in Streptomyces aizunenesis NRRL-B-11277, when purified from Escherichia coli, demonstrate the requisite enzyme activities for C5N formation and amide ligation. First, succinyl-CoA and glycine are condensed to generate 5-aminolevulinate (ALA) by a dedicated PLP-dependent ALA synthase (ORF34). Then ALA is converted to ALA-CoA through an ALA-AMP intermediate by an acyl-CoA ligase (ORF35). ALA-CoA is unstable and has a half-life of ～10 min under incubation conditions for off-pathway cyclization to 2,5-piperidinedione. The ALA synthase can compete with the nonenzymatic decomposition route and act in a novel second transformation, cyclizing ALA-CoA to C5N. C 5N is then a substrate for the third enzyme, an ATP-dependent amide synthetase (ORF33). Using octatrienoic acid as a mimic of the C56 polyenoic acid scaffold of ECO-02301, formation of the octatrienyl-C 5N product was observed. This three enzyme pathway is likely the general route to the C5N ring system in other natural products, including the antibiotic moenomycin.

Facile access to 5-hydroxy-2-piperidone derivatives. Synthesis of a homologous hydroxypiracetam

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