96886-56-5

Basic information

• Product Name: (S)-2-Amino-2-methyl-4-pentenoic acid
• Synonyms: L-alpha-Allylalanine;4-Pentenoicacid,2-amino-2-methyl-,(2R)-(9CI);L-α-Methylallylalanine;(S)-2-Amino-2-methyl-4-pentenoic acid;L-α-ALLYLALANINE;(R)-alpha-Allylalanine (>98%, >98%ee);H-alpha-All-L-Ala-OH;(R)-2-amino-2-methylpent-4-enoic acid
• CAS NO: 96886-56-5
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• Product Categories: GLYCINESCAFFOLD;Amino Acids;Chiral Reagent;unnatural amino acids;α-Methyl Amino Acids
• Mol File: 96886-56-5.mol
• Article Data: 20

Chemical Properties

• Melting Point: 296-299 °C
• Boiling Point: 226.178 °C at 760 mmHg
• Flash Point: 90.59 °C
• Appearance: /
• Density: 1.067 g/cm³
• Vapor Pressure: 0.03mmHg at 25°C
• Refractive Index: 1.484
• Storage Temp.: 2-8°C
• PKA: 2.26±0.10(Predicted)
• CAS DataBase Reference: (S)-2-Amino-2-methyl-4-pentenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Amino-2-methyl-4-pentenoic acid(96886-56-5)
• EPA Substance Registry System: (S)-2-Amino-2-methyl-4-pentenoic acid(96886-56-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 96886-56-5(Hazardous Substances Data)

Usage

General Description

(S)-2-Amino-2-methyl-4-pentenoic acid, also known as L-2-Amino-4-methyl-5-pentenoic acid or pipecolic acid, is a naturally occurring chemical compound. It is a cyclic amino acid that is found in many organisms, including plants, animals, and bacteria. Its structure consists of a five-carbon chain with a nitrogen atom and a double bond, making it a member of the pipecolic acid family. (S)-2-Amino-2-methyl-4-pentenoic acid has various biological activities and is believed to play a role in processes such as neurotransmission, immune response, and plant defense mechanisms. Additionally, it has potential therapeutic properties and is being studied for its potential role in the treatment of neurodegenerative diseases and autoimmune disorders.

InChI:InChI=1/C6H11NO2/c1-3-4-6(2,7)5(8)9/h3H,1,4,7H2,2H3,(H,8,9)/t6-/m1/s1

Upstream product

• 144125-67-7 C^α-methyl-D,L-allylglycinamide 
• 106-95-6 allyl bromide 
• 302-72-7 rac-Ala-OH 
• 56-41-7 L-alanin 
• 191284-36-3 (3S,6R)-3-Allyl-6-isopropyl-3-methyl-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one 
• 126402-81-1 isopropyl 2-[(E)-1-phenylmethylideneamino]propanoate 
• 144072-99-1 C^α-methyl-D-allylglycinamide 
• 53933-42-9 2-(benzylidene-amino)-propionic acid methyl ester 
• 91292-73-8 methyl alanine p-chlorobenzaldimine 
• 110510-45-7 (R)-2-Methyl-2-((3S,4R)-2-oxo-3-phenoxy-4-phenyl-azetidin-1-yl)-pent-4-enoic acid tert-butyl ester 
• 338-69-2 D-Alanine 

Downstream Products

• 129786-68-1 (R)-2-((tert-butoxycarbonyl)amino)-2-methylpent-4-enoic acid 
• 288617-71-0 (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid 

Relevant articles and documents

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.

Stereoselective functionalisation of cis- and trans-2-ferrocenyl-3- pivaloyl-4-alkyl-1,3-oxazolidin-5-ones: Asymmetric synthesis of (R)- and (S)-2-alkyl-2-aminopent-4-enoic acids and (2R,3S)-2-amino-2-methyl-3-hydroxy-3- phenylpropanoic acid

Treatment of a range of cis- and trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3- oxazolidin-5-ones with LDA followed by the addition of allyl bromide promotes highly stereoselective allylation (>98% de) at the 4-position of the oxazolidinone ring anti to the s

Chiral salen-metal complexes as novel catalysts for the asymmetric synthesis of α-amino acids under phase transfer catalysis conditions

Chiral salen-metal complexes have been tested as catalysts for the C-alkylation of Schiff's bases of alanine and glycine esters with alkyl bromides under phase-transfer conditions (solid sodium hydroxide, toluene, ambient temperature, 1-10 mol% of the catalyst). The best catalyst, which was derived from a Cu(II) complex of (1R, 2R or 1S,2S)-[N,N′-bis(2′-hydroxybenzylidene)]-1,2-diaminocyclohexane, gave α-amino and α-methyl-α-amino acids with enantiomeric excesses of 70-96%.