104261-87-2

Basic information

• Product Name: 2-Pyrrolidinecarboxamide, N-phenyl-, (2R)-
• Synonyms: H-D-Pro-NHPh;D-Proline anilide;(R)-2-phenylaminocarbonylpyrrolidine;(R)-N-phenylpyrrolidine-2-carboxamide;(R)-Pyrrolidine-2-carboxylic acid phenylamide;R-proline anilide
• CAS NO: 104261-87-2
• Molecular Formula: C11H14N2O
• Molecular Weight: 190.245
• Mol File: 104261-87-2.mol
• Article Data: 43

Chemical Properties

• CAS DataBase Reference: 2-Pyrrolidinecarboxamide, N-phenyl-, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinecarboxamide, N-phenyl-, (2R)-(104261-87-2)
• EPA Substance Registry System: 2-Pyrrolidinecarboxamide, N-phenyl-, (2R)-(104261-87-2)

Safety Data

• Hazardous Substances Data: 104261-87-2(Hazardous Substances Data)

Upstream product

• 101794-01-8 5-oxo-1-(toluene-4-sulfonyl)-L-prolin-anilide 
• 111492-63-8 (S)-proline acid chloride hydrochloride 
• 62-53-3 aniline 
• 220510-66-7 2-(phenylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 220510-58-7 tert-butyl (S)-2-(phenylcarbamoyl)pyrrolidine-1-carboxylate 
• 73096-29-4 1-(toluene-4-sulfonyl)-L-prolin-anilide 
• 103-71-9 phenyl isocyanate 
• 591-50-4 iodobenzene 
• 7531-52-4 L-prolinamide 
• 108-86-1 bromobenzene 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 54731-09-8 N-tosyl-L-prolyl chloride 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 147-85-3 L-proline 

Downstream Products

• 91704-70-0 (+)-(thenoyl-3)-2 phenyl-3 diazabicyclo-1,3<3,3,O>octane 
• 104261-76-9 3-methylene-2-phenyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]-[8aS]-pyrazine-1,4-dione 
• 104261-86-1 3-methylene-2-phenyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]-[8aR]-pyrazine-1,4-dione 
• 1173169-88-4 C₂₂H₂₆N₂O₂ 
• 1313735-03-3 C₁₈H₂₀N₂O₂ 
• 403617-25-4 C₃₀H₃₃FN₄O₂ 

Relevant articles and documents

Synthesis and anticancer activity of conformationally constrained Smac mimetics containing pseudo β turns

Herein, we report synthesis and in vitro anticancer activity of conformationally constrained Smac mimetics containing reverse turn inducing motifs “Ant-Pro” and “sAnt-Pro”. The synthesis of Smac analogs with diverse hydrophobic groups at the C-

Use of amino amides derived from proline as chiral ligands in the ruthenium(II)-catalyzed transfer hydrogenation reaction of ketones

We developed an efficient, easily available, and easy to use proline amide-based ruthenium(II) catalysts for the asymmetric hydride transfer reduction of prochiral ketones and e.e.s up to 98.8% have been measured.

Enantiomerically pure cyclopalladated diazaphospholidine

Enantiomerically pure (S)-2-(anilinomethyl)pyrrolidine (S)-2 was obtained from (S)-proline using a modified four-step procedure in a total yield of 56%. Diamine (S)-2 was converted to diazaphospholidine (S)-1 using oTolP(NMe2)2

Dynamic thermodynamic and dynamic kinetic resolution of 2-lithiopyrrolidines

Dynamic resolution has been studied as a method for the asymmetric synthesis of 2-substituted pyrrolidines. Highly enantioselective electrophilic substitutions of racemic 2-lithiopyrrolidines in the presence of a chiral ligand have been achieved. The organolithium compounds were prepared by tin-lithium exchange from the corresponding tributylstannanes and n-butyllithium or by deprotonation of N-(tert-butyloxycarbonyl)-pyrrolidine with sec-butyllithium. A range of N-substituents and chiral ligands were investigated for the dynamic resolution. Electrophilic quench of the resolved diastereomeric 2-lithiopyrrolidine-chiral ligand complexes provided the enantiomerically enriched 2-substituted pyrrolidines. With N-alkyl derivatives, the resolution occurs conveniently at (or just below) room temperature and either enantiomer of the product can be formed by appropriate choice of the chiral ligand. The asymmetric induction occurs as a result of a thermodynamic preference for one of the diastereomeric complexes. The minor complex was found to have a faster rate of reaction with the electrophile. The use of N-allylic derivatives provides a means to prepare the N-unsubstituted pyrrolidine products. Best results were obtained with the N-2,3-dimethylbut-2-enyl derivative, and this N-substituent could be cleaved using 1-chloroethyl chloroformate. With N-Boc-2- lithiopyrrolidine, the enantioselectivity arises by a kinetic resolution and high levels of asymmetric induction in the presence of excess n-butyllithium can be obtained. Dynamic kinetic resolution of the N-Boc derivative is limited in the scope of electrophile that can be used.

Design, synthesis, and insecticidal activities of novel diamide derivatives with alpha-amino acid subunits

A series of diamide derivatives containing α-amino acids were designed and synthesized. These compounds were evaluated for their insecticidal activities against Plutella xylostella, Mythimna separate, Myzus persicae, and Tetranychus cinnabarinus. Most of the title compounds containing an l-phenylglycine skeleton were endowed with good activities at the concentration of 500 mg·L?1. Compounds (R)-A6 showed a potential value for further optimization as an insecticidal lead with the LC50 value of 86.8 mg·L?1.

Chiral azo-heterocyclic carbene precursor compound with bicyclic framework and preparation method thereof

The invention discloses a chiral azo-heterocyclic carbene precursor compound with a bicyclic framework and a preparation method thereof. A series of the chiral azo-heterocyclic carbene precursor compound with the bicyclic framework is obtained by taking c