4071-39-0

Basic information

• Product Name: α-Allokainic acid
• Synonyms: α-Allokainic acid;(2S)-2-Carboxy-4α-(1-methylethenyl)-3β-pyrrolidineacetic acid;(2S)-2α-Carboxy-4α-(1-methylethenyl)-3β-pyrrolidineacetic acid;L-α-Allokainic acid;alpha-Allokainic acid
• CAS NO: 4071-39-0
• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.2304
• Mol File: 4071-39-0.mol
• Article Data: 18

Chemical Properties

• Melting Point: 237-238 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 439.9°Cat760mmHg
• Flash Point: 219.8°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 5.74E-09mmHg at 25°C
• Refractive Index: 1.508
• PKA: 2.03±0.60(Predicted)
• CAS DataBase Reference: α-Allokainic acid(CAS DataBase Reference)
• NIST Chemistry Reference: α-Allokainic acid(4071-39-0)
• EPA Substance Registry System: α-Allokainic acid(4071-39-0)

Safety Data

• Hazardous Substances Data: 4071-39-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15)/t6-,7?,9?/m0/s1

Upstream product

• 102371-35-7 (1,2-bis-ethoxycarbonyl-4-isopropenyl-pyrrolidin-3-yl)-malonic acid diethyl ester 
• 102944-08-1 [1,2-bis-ethoxycarbonyl-4-(β-dimethylamino-isopropyl)-pyrrolidin-3-yl]-malonic acid diethyl 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 
• 98133-48-3 (+/-)-(2Ξ)-4t-((Ξ)-β-hydroxy-isopropyl)-3t-methoxycarbonylmethyl-pyrrolidine-1,2r-dicarboxylic acid-1-ethyl ester-2-methyl ester 
• 108072-03-3 (2R,3S,4R)-1-Benzyl-4-isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid 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 
• 111563-55-4 N-Boc-3-carboxymethyl-4-(i-propenyl)-2-pyrrolidinecarboxylic acid dimethyl ester 
• 75466-86-3 N-Boc kainic acid 
• 132286-59-0 Benzoic acid (2S,3S,4S)-1-benzoyl-4-isopropenyl-3-methoxycarbonylmethyl-pyrrolidin-2-ylmethyl ester 
• 108984-59-4 (2R,3R,4R)-1-Benzoyl-4-isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid methyl ester 
• 87682-50-6 (+/-)-4t-isopropenyl-3t-methoxycarbonylmethyl-pyrrolidine-1,2r-dicarboxylic acid-1-ethyl ester-2-methyl ester 

Downstream Products

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

Substrate stereocontrol in the intramolecular organocatalyzed tsuji-trost reaction: Enantioselective synthesis of allokainates

Organocatalyzed Tsuji-Trost cyclization of 3b proceeds with asymmetric induction and allows for stereoselective synthesis of (+)-allokainic acid. The stereochemical outcome of the cyclization was predicted by calculations.

Di- and trisubstituted γ-lactams via Rh(II)-carbenoid reaction of N -Cα-branched, N -Bis(trimethylsilyl)methyl α-diazoamides. Synthesis of (±)-α-allokainic acid

Acyclic N-Cα-branched, N-bis(trimethylsilyl)methyl (N-BTMSM) diazoamides undergo regio-, chemo-, and diastereoselective Rh(II)-carbenoid C-H insertion to give 4,5-disubstituted and 3,4,5-trisubstituted γ-lactams. The conformational influence of