5768-79-6

Basic information

• Product Name: Hexahydro-3H-pyrrolo[1,2-c]imidazole-1,3-dione
• Synonyms: 1,5-Trimethylenehydantoin;5,6,7,7a-Tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione;Hexahydro-1H-pyrrolo[1,2-c]imidazole-1,3-dione;Hexahydro-3H-pyrrolo[1,2-c]imidazole-1,3-dione;Prolinehydantoin;1,4,5,6-tetrahydropyrrolo[3,4-d]iMidazole;1,2-Pyrrolidinedicarboximide;5,6,7,7a-tetrahydropyrrolo[2,1-e]imidazole-1,3-dione
• CAS NO: 5768-79-6
• Molecular Formula: C₆H₈N₂O₂
• Molecular Weight: 140.14
• Mol File: 5768-79-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.4g/cm³
• Refractive Index: 1.585
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Hexahydro-3H-pyrrolo[1,2-c]imidazole-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: Hexahydro-3H-pyrrolo[1,2-c]imidazole-1,3-dione(5768-79-6)
• EPA Substance Registry System: Hexahydro-3H-pyrrolo[1,2-c]imidazole-1,3-dione(5768-79-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5768-79-6(Hazardous Substances Data)

Usage

General Description

Hexahydro-3H-pyrrolo[1,2-c]imidazole-1,3-dione, also known as L-proline lactam, is a heterocyclic compound consisting of a hexahydro-3H-pyrrolo ring fused to an imidazole ring with a carbonyl group at the 1 and 3 positions. It is an important building block for various pharmaceuticals, agrochemicals, and natural products. L-proline lactam has been found to exhibit diverse biological activities, including antitumor, antiviral, and antibacterial properties. Its unique structural features and potential therapeutic applications make it a valuable target for chemical synthesis and pharmacological research.

InChI:InChI=1/C6H8N2O2/c9-5-4-2-1-3-8(4)6(10)7-5/h4H,1-3H2,(H,7,9,10)

Upstream product

• 609-36-9 rac-Pro-OH 
• 367906-67-0 N-cyanoproline methyl ester 
• 147-85-3 L-proline 
• 93188-01-3 2-(aminocarbonyl)-1-pyrrolidinecarboxylic acid, phenylmethyl ester 
• 590-28-3 potassium cyanate 
• 108-91-8 cyclohexylamine 
• 81965-44-8 N-(2-chloroethyl)-N-nitrosocarbamoyl prolinamide 

Downstream Products

• 1000848-82-7 (±)-2-tosylhexahydro-3H-pyrrolo[1,2-c]imidazole-3-one 
• 92763-94-5 3-<3-(m-methoxyphenyl)propyl>-1,3-diazabicyclo<3.3.0>octane-2,4-dione 

Relevant articles and documents

3-(Triflyloxy)benzynes Enable the Regiocontrolled Cycloaddition of Cyclic Ureas to Synthesize 1,4-Benzodiazepine Derivatives

A versatile synthesis of 1,4-benzodiazepine derivatives through the reaction of various 3-(trifluoromethanesulfonyloxy)benzynes with N -(p -toluenesulfonyl)imidazolidin-2-ones is reported. This reaction system provides a 1,4-benzodiazepine bearing a trifluoromethanesulfonyloxy group as a single regioisomer among the four possible regioisomers.

Decomposition of N-(2-chloroethyl)-N-nitrosocarbamoyl amino acid amides

The chemical decomposition of N-(2-chloroethyl)-N-nitrosocarbamoyl (Q(NO)) prolinamide and valinamide were studied under physiological conditions. The volatile products were identified with GC. Q(NO)-Pro-NH2 gave twice the amount of ethylene glycol and only one-fifth of the 2-chloroethanol produced by Q(NO)-Val-NH2 or BCNU, pointing to different pathways of their decomposition. The carbamoylating activity was also investigated in the presence of cyclohexylamine, and it was found to lead mainly to intramolecular carbamoylation with the formation of hydantoin derivatives.