60169-72-4

Basic information

• Product Name: 1-N-BENZYL-PROLINE
• Synonyms: 1-(Phenylmethyl)-DL-proline;1-benzylproline(SALTDATA: HCl);DL-N-Benzylproline;N-benzylproline;Proline, 1-(phenylmethyl)-;(2S)-1-(benzyl)proline;(2S)-1-(benzyl)pyrrolidin-1-ium-2-carboxylate;(2S)-1-(phenylmethyl)-2-pyrrolidin-1-iumcarboxylate
• CAS NO: 60169-72-4
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.255
• Mol File: 60169-72-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 170-170.5 °C
• Boiling Point: 343.1±35.0 °C(Predicted)
• Appearance: /
• Density: 1.205±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.35±0.20(Predicted)
• CAS DataBase Reference: 1-N-BENZYL-PROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-N-BENZYL-PROLINE(60169-72-4)
• EPA Substance Registry System: 1-N-BENZYL-PROLINE(60169-72-4)

Safety Data

• Hazardous Substances Data: 60169-72-4(Hazardous Substances Data)

Usage

General Description

1-N-Benzyl-proline is a chemical compound with the molecular formula C13H17NO2. It is a derivative of the amino acid proline, with a benzyl group attached to the nitrogen atom. 1-N-Benzyl-proline has been widely used in the synthesis of peptide-based drugs and pharmaceuticals due to its ability to enhance the biological properties of these compounds. It has also been studied for its potential medicinal properties, including its role as an antioxidant and its ability to inhibit certain enzymes. Additionally, 1-N-Benzyl-proline has been investigated for its potential use in the treatment of neurological disorders, cancer, and viral infections, making it an important compound in medicinal chemistry research.

Upstream product

• 100-44-7 benzyl chloride 
• 609-36-9 rac-Pro-OH 
• 100-39-0 benzyl bromide 
• 147-85-3 L-proline 

Downstream Products

• 61352-48-5 ethyl N-(N-benzyl-2-pyrrolidinylcarbonyl)-N-methylanthranilate 
• 67131-44-6 1-benzyl-2-(hydroxymethyl)pyrrolidine 
• 19133-99-4 3-(1-benzyl-pyrrolidin-2-yl)-7-methyl-indole 

Relevant articles and documents

Discovery of novel n-substituted prolinamido indazoles as potent rho kinase inhibitors and vasorelaxation agents

Inhibitors of Rho kinase (ROCK) have potential therapeutic applicability in a wide range of diseases, such as hypertension, stroke, asthma and glaucoma. In a previous article, we described the lead discovery of DL0805, a new ROCK I inhibitor, showing potent inhibitory activity (IC50 6.7 μM). Herein, we present the lead optimization of compound DL0805, resulting in the discovery of 24- and 39-fold more-active analogues 4a (IC50 0.27 μM) and 4b (IC50 0.17 μM), among other active analogues. Moreover, ex-vivo studies demonstrated that 4a and 4b exhibited comparable vasorelaxant activity to the approved drug fasudil in rat aortic rings. The research of a preliminary structure-activity relationship (SAR) indicated that the target compounds containing a β-proline moiety have improved activity against ROCK I relative to analogues bearing an β-proline moiety, and among the series of the derivatives with a β-proline-derived indazole scaffold, the inhibitory activity of the target compounds with a benzyl substituent is superior to those with a benzoyl substituent.

Palladium(II)-N-heterocyclic carbene complexes derived from proline: Synthesis and characterization

Pd(II)-N-heterocyclic carbene complexes derived from proline have been successfully synthesized in good yields and their structures have been characterized by X-ray single crystal diffraction. It was found that the substituents on the N-atom of the pyrrolidine skeleton dramatically affect on the coordination pattern of the palladium complexes. In a word, when an electron-rich group as benzyl group was attached on the N-atom, both of the N-atom and NHC were coordinated to the Pd(II) center; while when an electron-poor group as Ts group was attached, a dimeric mono-coordinated Pd(II)-NHC was obtained exclusively.

Use of Chloroalkenylamines for the Synthesis of 1-Azabicyclooctane and 1-Azabicyclononane Derivatives

Various N-(chloroprop-2-enyl)-, N-(3-chlorobut-2-enyl)-, N-(4-chloropent-3- and -4-enyl)-proline derivatives, -succinimides, and -phthalimides have been synthesised and subjected to Lewis acid treatment.The following gave fruitful results: N-(4-chloropent-3-enyl)-5-hydroxy-2-pyrrolidone (25) gave 1-acetyl-1,2,3,6,7,7a-hexahydropyrrolizin-5-one (28); N-(4-chloropent-3-enyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (30) gave 1-endo-acetyl-1,2,3,9b-tetrahydropyrroloisoindol-5-one (31) which was isomerised to the exo-isomer; N-(4-chloropent-3-enyl)-3-methylene-2,3-dihydro- 1H-isoindol-1-one (34) and N-(4-chloropent-3-enyl)-3-hydroxy-3-methyl-2,3-dihydro-1H-isoindol-1-one (33) gave 1-endo-acetyl-9b-methyl-1,2,3,9b-tetrahydropyrroloisoindol-5-one (35); N-proline (42) gave 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrroloisoquinoline (43), N-(2-chloroprop-2-enyl)-2-(2-hydroxy-2-propyl)pyrrolidine (44) gave 6-chloro-8,8-dimethyl-1,2,3,5,8,8a-hexahydroindolizine (47) and 8,8-dimethyl-1,2,3,7,8,8a-hexahydroindolizin-6(5H)-one (48) which were reduced to the corresponding alcohols; N-(4-chloropent-4-enyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (50) gave 7,8,11,11a-tetrahydro-5H-azepinoisoindole-5,10(9H)-dione (51).