103290-40-0

Basic information

• Product Name: (2S,4R)-4-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID
• Synonyms: (2S,4R)-4-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID;(4R)-4-Phenyl-L-proline;cis-4-Phenyl-L-proline
• CAS NO: 103290-40-0
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.229
• Mol File: 103290-40-0.mol

Chemical Properties

• Boiling Point: 372.8 °C at 760 mmHg
• Flash Point: 179.3 °C
• Appearance: /
• Density: 1.186
• Vapor Pressure: 3.22E-06mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (2S,4R)-4-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-4-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID(103290-40-0)
• EPA Substance Registry System: (2S,4R)-4-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID(103290-40-0)

Safety Data

• Hazardous Substances Data: 103290-40-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S,4R)-4-Phenylpyrrolidine-2-carboxylic acid is used as a key intermediate in the synthesis of pharmaceuticals for its unique reactivity and structural features. It contributes to the development of new drugs with improved therapeutic properties and potential applications in various medical fields.
Used in Agrochemical Development:
In the agrochemical industry, (2S,4R)-4-Phenylpyrrolidine-2-carboxylic acid serves as a crucial building block for the synthesis of novel agrochemicals. Its unique structure and reactivity enable the creation of new chemical entities with enhanced pesticidal or herbicidal properties, contributing to more effective and sustainable agricultural practices.
Used in Organic Synthesis:
(2S,4R)-4-Phenylpyrrolidine-2-carboxylic acid is utilized as a versatile building block in organic synthesis, allowing the construction of a wide range of chemical entities. Its unique structure and reactivity facilitate the synthesis of complex molecules, which can be further explored for potential applications in various industries, such as pharmaceuticals, materials science, and agrochemicals.
Used in Materials Science:
The phenyl group present in (2S,4R)-4-Phenylpyrrolidine-2-carboxylic acid confers certain properties that make it suitable for use in materials science. It can be incorporated into the design and synthesis of new materials with specific characteristics, such as improved mechanical strength, thermal stability, or optical properties, for applications in various industries, including electronics, automotive, and aerospace.

InChI:InChI=1/C11H13NO2/c13-11(14)10-6-9(7-12-10)8-4-2-1-3-5-8/h1-5,9-10,12H,6-7H2,(H,13,14)/t9-,10-/m0/s1

Upstream product

• 99859-73-1 3-chloro-5-phenyl-piperidin-2-one 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 3973-63-5 5-phenylpiperidin-2-one 
• 591-51-5 phenyllithium 
• 57653-38-0 N-<(phenylmethoxy)carbonyl>-4(R)-<<(4-methylphenyl)sulfonyl>oxy>-(S)-proline methyl ester 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 336818-78-1 (2S,4R)-1-(tert-butoxycarbonyl)-4-phenyl-2-pyrrolidinecarboxylic acid 
• 78464-03-6 N-(benzyloxycarbonyl)-cis-4-hydroxy-trans-4-phenyl-L-proline 
• 82087-66-9 N-(benzyloxycarbonyl)-3,4-dehydro-4-phenyl-L-proline 
• 99854-36-1 3,3-dichloro-5-phenyl-piperidin-2-one 

Downstream Products

• 785001-74-3 cis-4-cyclohexyl-L-proline 
• 83624-30-0 (2S,4R)-1-{2-[Hydroxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-4-phenyl-pyrrolidine-2-carboxylic acid 
• 83624-20-8 (2S,4R)-4-Cyclohexyl-1-{2-[hydroxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid 
• 83624-19-5 (2S,4R)-4-Cyclohexyl-1-{2-[ethoxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid 
• 1093651-96-7 (2S,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid 

Relevant articles and documents

Macrocyclic inhibitors of the PD-1/PD-L1 and CD80(B7-1)/PD-L1 protein/protein interactions

The present disclosure provides novel macrocyclic peptides which inhibit the PD-1/PD-L1 and PD-L1/CD80 protein/protein interaction, and thus are useful for the amelioration of various diseases, including cancer and infectious diseases.

Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines

Analogues of captopril, enalaprilat, and the phosphinic acid [[hydroxy(4-phenylbutyl)phosphinyl]acetyl)-L-proline incorporating 4-substituted proline derivatives have been synthesized and evaluated as inhibitors of angiotensin-converting enzyme (ACE) in vitro and in vivo. The 4-substituted prolines, incorporating alkyl, aryl, alkoxy, aryloxy, alkylthio, and arylthio substituents were prepared from derivatives of 4-hydroxy- and 4-ketoproline. In general, analogues of all three classes of inhibitors with hydrophobic substituents on proline were more potent in vitro than the corresponding unsubstituted proline compounds. 4-Substituted analogues of captopril showed greater potency and duration of action than the parent compound as inhibitors of the angiotensin I induced pressor response in normotensive rats. The S-benzoyl derivative of cis-4-(phenylthio)captopril, zofenopril, was found to be one of the most potent compounds of this class and is now being evaluated clinically as an antihypertensive agent. In the phosphinic acid series, the 4-ethylenethioketal and trans-4-cyclohexyl derivatives were found to be the most potent compounds in vitro and in vivo. A prodrug of the latter compound, fosinopril, is also being evaluated in clinical trials.

LITHIUM DIPHENYLCUPRATE REACTIONS WITH 4-TOSYLOXY-L-PROLINES; AN INTERESTING STEREOCHEMICAL OUTCOME. A SYNTHESIS OF TRANS-4-PHENYL-L-PROLINE.

The reaction of lithium diphenylcuprate with trans-4- and cis-4-tosyloxy-L-prolines gives excellent yields of 4-phenyl substituted L-prolines and the reaction proceeds with net retention of configuration at the carbon center bearing the tosyloxy group.

Method for making substituted prolines

A method is provided for making substituted prolines of the structure STR1 wherein X is lower alkyl or aryl, R is H, lower alkyl or an alkali metal and Z is an N-protecting group, which method includes the step of reacting a compound of the structure STR2