31795-93-4

Basic information

• Product Name: N-BENZYL-L-PROLINE
• Synonyms: (S)-1-N-(benzyl)-L-proline;(2S)-1-Benzylpyrrolidin-2-ylcarboxylic Acid;(S)-Benzylproline;1-(PhenylMethyl)-L-proline;1-(phenylnethyl)-L-proline;L-Proline, 1-(phenylmethyl)-;1-(benzyl)-L-proline;(S)-Benzyl-pyrrolidine-2-carboxylic acid
• CAS NO: 31795-93-4
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.25
• Product Categories: pharmacetical;Amino Acid Derivatives;Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Chiral Reagents
• Mol File: 31795-93-4.mol
• Article Data: 31

Chemical Properties

• Melting Point: 168-171°C
• Boiling Point: 343.1 °C at 760 mmHg
• Flash Point: 161.3 °C
• Appearance: white solid
• Density: 1.205
• Vapor Pressure: 2.76E-05mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Store at 0-5°C
• Solubility: Acetone (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• PKA: 2.35±0.20(Predicted)
• CAS DataBase Reference: N-BENZYL-L-PROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYL-L-PROLINE(31795-93-4)
• EPA Substance Registry System: N-BENZYL-L-PROLINE(31795-93-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 31795-93-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 31795-93-4 differently. You can refer to the following data:
1. A reagent for the synthesis of optically pure a-amino-acids
2. A reagent for the synthesis of optically pure α-amino-acids.

InChI:InChI=1/C12H15NO2/c14-12(15)11-7-4-8-13(11)9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,14,15)/t11-/m0/s1

Upstream product

• 100-44-7 benzyl chloride 
• 147-85-3 L-proline 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 90741-31-4 (S)-N-benzyl-5-thioxoproline tert-butyl ester 
• 100-52-7 benzaldehyde 
• 170642-58-7 (S)-N-benzylproline tert-butyl ester 
• 955-40-8 N-benzyl-L-proline ethyl ester 
• 71989-31-6 Fmoc-Pro-OH 
• 83528-04-5 (S)-N-benzyl-O-benzylpyrrolidine-2-carboxylate 

Downstream Products

• 151264-96-9 1-benzyl-pyrrolidine-2-carboxylic acid tert-butylamide 
• 151265-00-8 (S)-1-Benzyl-pyrrolidine-2-carboxylic acid butylamide 
• 862902-30-5 N,N'-dibenzyl-L-prolinamide 
• 1186302-24-8 (L)-1-benzylpyrrolidine-2-carboxylic acid {3-[4-(2,6-dichlorophenyl)piperidine-1-yl]propyl}amide 
• 193345-58-3 N-{4-(2-Amino-4-thiazolyl)phenyl}-1-(phenylmethyl)-2 (S)-pyrrolidinecarboxamide 
• 205388-64-3 (2S)-2-(1-Oxo-4-phenyl)butyl-N-benzylpyrrolidine 
• 354563-94-3 ((2S)-1-Benzylpyrrolidin-2-yl)-[4-(4-fluorophenoxy)-piperidin-1-yl]-methanone Hydrochloride 
• 661452-55-7 ((2S)-1-Benzyl-pyrrolidin-2-yl)-[4-(4-fluoro-benzyl)-piperazin-1-yl]methanone 
• 354564-42-4 ((2S)-1-Benzylpyrrolidin-2-yl)-[4-(4-fluorobenzylidene)-piperidin-1-yl)-methanone hydrochloride 
• 661452-54-6 ((2S)-1-Benzylpyrrolidin-2-yl)-[4-(4-fluorophenyl)-piperazin-1-yl)-methanone hydrochloride 
• 354563-95-4 ((2S)-1-Benzylpyrrolidin-2-yl)-[4-(4-fluorobenzyl)-piperidin-1-yl]-methanone Hydrochloride 

Relevant articles and documents

Conformational analysis and mu-opioid receptor affinity of short peptides, endomorphin models in a low polarity solvent.

Peptide carbamates containing the sequence H-Pro-Trp-PheNH2 showed in CDCl3 restricted conformations stabilized by the presence of a gamma-turn. To test the reliability of the peptides as endomorphin conformational models, we measured the affinities for mu-receptors labelled with [3H]-DAMGO. In particular, Cbz-Pro-Trp-PheNH2 displayed a nanomolar affinity.

Improved synthesis of proline-derived Ni(II) complexes of glycine: Versatile chiral equivalents of nucleophilic glycine for general asymmetric synthesis of α-amino acids

A synthetically practical and operationally convenient method for preparing (S)-2-[N-(N′-benzylprolyl)-amino]benzophenone (BPBP) and hitherto unknown (S)-2-[N-(N′-benzylprolyl)amino]-4-methylbenzophenone (4-Me-BPBP), (S)-2-[N-(N′-benzylprolyl)amino]-5-nitrobenzophenone (5-NO2-BPBP), and their corresponding Ni(II) complexes with glycine [GlyNi(II)BPBP], a widely used chiral equivalent of nucleophilic glycine, and new analogues [GlyNi(II)-4-Me-BPBP] and [GlyNi(II)-5-NO2-BPBP] is described. The key step of the method is the synthetically efficient amid bond formation between the corresponding o-aminobenzophenones, featuring significant steric shielding and low nucleophilicity of the amino functionality as well as sterically constrained (S)-N-benzylproline (BP).

Preparation of labeled aromatic amino acids: Via late-stage18F-fluorination of chiral nickel and copper complexes

A general protocol for the preparation of 18F-labeled AAAs and α-methyl-AAAs applying alcohol-enhanced Cu-mediated radiofluorination of Bpin-substituted chiral complexes using Ni/Cu-BPX templates as double protecting groups is reported. The chiral auxiliaries are easily accessible from commercially available starting materials in a few synthetic steps. The versatility of the method was demonstrated by the high-yielding preparation of a series of [18F]F-AAAs and the successful implementation of the protocol into automated radiosynthesis modules. This journal is

Synthesis of Chiral Spin-Labeled Amino Acids

Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled l-amino acids is described, starting from readily available 2,2,6,6-tetramethyl-4-piperidinone. These SLAAs better replicate canonical residues in proteins and aim for biological incorporation via genetic incorporation or solid-phase peptide synthesis.