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

Uses

Piperidine-2,5-dione is used in preparation of piperidine-dione from aminoglutaric acid via lactonization, reduction, azidation, reductive ring expansion and Dess-Martin Periodinane oxidation.

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

Upstream product

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

Downstream Products

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