59905-23-6

Basic information

• Product Name: (3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-yl-D-proline
• CAS NO: 59905-23-6
• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.2304
• Mol File: 59905-23-6.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 439.9°C at 760 mmHg
• Flash Point: 219.8°C
• Density: 1.22g/cm³
• Vapor Pressure: 5.74E-09mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: (3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-yl-D-proline(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-yl-D-proline(59905-23-6)
• EPA Substance Registry System: (3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-yl-D-proline(59905-23-6)

Safety Data

• Hazardous Substances Data: 59905-23-6(Hazardous Substances Data)

Usage

General Description

The chemical compound "(3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-yl-D-proline" is a proline derivative with a molecular formula of C10H15NO4. It is a chiral compound, meaning it has specific spatial arrangement of its atoms. The compound contains a carboxymethyl group and a prop-1-en-2-yl side chain attached to a D-proline structure. (3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-yl-D-proline is commonly used in organic synthesis and pharmaceutical applications due to its unique structure and potential biological activity. Its stereochemical properties and functional groups make it a valuable building block for creating complex molecular structures.

Upstream product

• 108072-03-3 (2R,3S,4R)-1-Benzyl-4-isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid methyl ester 
• 77632-78-1 (-)-menthyl(Z)-4,4-diethoxycarbonyl-4--2-butenoate 
• 101020-91-1 (+/-)-[(3Ξ)-2t-carboxy-4t-((Ξ)-β-hydroxy-isopropyl)-pyrrolidin-3r-yl]-acetic acid 
• 108984-59-4 (2R,3R,4R)-1-Benzoyl-4-isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid methyl ester 
• 132286-59-0 Benzoic acid (2S,3S,4S)-1-benzoyl-4-isopropenyl-3-methoxycarbonylmethyl-pyrrolidin-2-ylmethyl ester 
• 132286-62-5 ((2R,3R,4R)-1-Benzoyl-2-hydroxymethyl-4-isopropenyl-pyrrolidin-3-yl)-acetic acid methyl ester 
• 101020-91-1 (+/-)-[(3Ξ)-2t-carboxy-4c-((Ξ)-β-hydroxy-isopropyl)-pyrrolidin-3r-yl]-acetic acid 
• 100453-82-5 (+/-)-[(3Ξ)-4c-((Ξ)-β-ethoxy-isopropyl)-2t-carboxy-pyrrolidin-3r-yl]-acetic acid 
• 98133-48-3 (+/-)-(2Ξ)-4t-((Ξ)-β-hydroxy-isopropyl)-3t-methoxycarbonylmethyl-pyrrolidine-1,2r-dicarboxylic acid-1-ethyl ester-2-methyl ester 
• 96429-43-5 (E)-6-((tert-butyldimethylsilyl)oxy)hex-3-en-2-one 
• 108072-02-2 (2R,3S,4R)-1-Benzyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-isopropenyl-pyrrolidine-2-carboxylic acid methyl ester 
• 96429-03-7 (2R,3S,4S)-4-Acetyl-1-benzyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-pyrrolidine-2-carboxylic acid methyl ester 

Downstream Products

• 487-79-6 (-)-kainic acid 
• 125292-93-5 [(3S)-2t-carboxy-4t-(α-hydroxy-isopropyl)-pyrrolidin-3r-yl]-acetic acid 

Relevant articles and documents

Synthesis of (±)-β-Allokainic Acid

The total synthesis of kainoid alkaloid, (+/–)-β-allokainic acid is reported. The key step is a vinylogous Cloke–Wilson rearrangement followed by Lewis acid and transition metal induced transformations to prepare a highly functionalized pyrrolidine suitable for conversion to the target molecule.

Total synthesis of (±)-kainic acid: A photochemical C-H carbamoylation approach

A novel photochemical C-H carbamoylation of an octahydroisoindole derivative with PhNCO has allowed the authors to provide a unique access to a highly functionalized proline motif from which total synthesis of (±)-kainic acid, a bioactive marine alkaloid, has been accomplished.

Stereocontrolled syntheses of kainoid amino acids from 7-azabicyclo[2.2.1] heptadienes using tandem radical addition-homoallylic radical rearrangement

N-Boc syn-7-(2-hydroxyethyl)-4-(alkyl or aryl)sulfonyl-2-azabicyclo[2.2.1] hept-5-enes serve as precursors in syntheses of the neuroexcitants 3-(carboxymethyl)pyrrolidine-2,4-dicarboxylic acid 43, α-kainic acid 12, α-isokainic acid 14, and α-dihydroalloka