329012-80-8

Basic information

• Product Name: (R)-1-N-Cbz-3-cyanopyrrolidine
• Synonyms: (r)-1-n-cbz-3-cyanopyrrolidine;(R)-1-Cbz-3-cyanopyrrolidine;3-Cyano-1-pyrrolidinecarboxylic acid phenylmethyl ester;1-Pyrrolidinecarboxylic acid, 3-cyano-, phenylmethyl ester, (3R)-
• CAS NO: 329012-80-8
• Molecular Formula: C₁₃H₁₄N₂O₂
• Molecular Weight: 230.26246
• Product Categories: Pyrrole&Pyrrolidine&Pyrroline
• Mol File: 329012-80-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.20
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-1-N-Cbz-3-cyanopyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-N-Cbz-3-cyanopyrrolidine(329012-80-8)
• EPA Substance Registry System: (R)-1-N-Cbz-3-cyanopyrrolidine(329012-80-8)

Safety Data

• Hazardous Substances Data: 329012-80-8(Hazardous Substances Data)

Usage

General Description

"(R)-1-N-Cbz-3-cyanopyrrolidine" is a complex organic compound belonging to the class of pyrrolidines which are saturated organic compounds containing a pyrrolidine ring. The '(R)' in its chemical name refers to the configuration of the chiral center, indicating its spatial arrangement. 'Cbz' refers to 'carboxybenzyl,' representing a protective group attached to the nitrogen atom, which is commonly used in organic synthesis to protect amines. The term '3-cyanopyrrolidine' indicates the presence of a cyano group (carbon-nitrogen triple bond) attached to the third carbon of the pyrrolidine ring. (R)-1-N-Cbz-3-cyanopyrrolidine is primarily important in both scientific research and pharmaceutical development, although specific applications may vary based on its chemical properties.

Upstream product

• 188846-99-3 (+/-)-3-cyanopyrrolidine-1-carboxylic acid benzyl ester 
• 501-53-1 benzyl chloroformate 
• 100858-33-1 (3R)-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester 
• 151-50-8 potassium cyanide 
• 158654-83-2 benzyl (3S)-3-(p-tolylsulfonyloxy)pyrrolidine-1-carboxylate 
• 100858-32-0 (S)-3-hydroxy-1-pyrrolidinecarboxylic acid phenylmethyl ester 

Downstream Products

• 192214-06-5 (R)-1-((benzyloxy)-carbonyl)pyrrolidine-3-carboxylic acid 

Relevant articles and documents

Nitrilase-catalyzed enantioselective synthesis of pyrrolidine- And piperidinecarboxylic acids

The enantioselective synthesis of the nonproteinogenic amino acids β-proline and nipecotic acids from their readily available nitriles is achieved in high enantiomeric excess by commercially available nitrilases. The presented procedure comprises not more than 4 steps, thus considerably reducing the multiple steps generally required. Amide formation is also observed for specific heterocyclic nitriles.

Synthesis and binding activity of endomorphin-1 analogues β-amino acids

Endomorphin-1 (Tyr-Pro-Trp-PheNH2) has been proposed as the most potent endogenous ligand of the μ-opioid receptors. In this paper, we describe the synthesis of some endomorphin-1 based tetrapeptides in which a residue of the sequence Tyr-Pro-Trp-PheNH2 is replaced by the corresponding β-isomer. These novel peptides showed different affinities for the opioid receptors labeled with [3H]-DAMGO in rat brain membranes, depending on the β-amino acid. In particular, the tetrapeptide containing β-Pro (Tyr-β-(R)-Pro-Trp-PheNH2) displayed a higher affinity than endogenous endomorphin-1, as revealed by their K(i) values (0.33 and 11.1 nM, respectively). (C) 2000 Elsevier Science Ltd.