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

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

Uses

Used in Pharmaceutical Industry:
(S)-2-Amino-2-methyl-4-pentenoic acid is utilized as a pharmaceutical compound for its potential therapeutic effects. It is being studied for its role in the treatment of neurodegenerative diseases, where it may help mitigate the progression of conditions such as Alzheimer's and Parkinson's disease by modulating neurotransmission pathways.
Used in Immunology Research:
In the field of immunology, (S)-2-Amino-2-methyl-4-pentenoic acid serves as a research tool to understand its influence on immune response mechanisms. This knowledge can contribute to the development of immunomodulatory therapies and treatments for autoimmune disorders.
Used in Agricultural Industry:
(S)-2-Amino-2-methyl-4-pentenoic acid is employed in agriculture, particularly in the study of plant defense mechanisms. Understanding its role in plants can lead to the development of more effective strategies for crop protection against pathogens and pests, thereby enhancing crop yields and food security.
Used in Chemical Synthesis:
In the chemical synthesis industry, (S)-2-Amino-2-methyl-4-pentenoic acid may be used as a building block or intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals, due to its unique structural features and reactivity.

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

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

Downstream Products

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

Rapid asymmetric synthesis of amino acids via NiII complexes based on new fluorine containing chiral auxiliaries

New fluorine-containing chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(2- fluorobenzyl)-, (S)-N-(2-benzoylphenyl)-1-(3-fluorobenzyl)-, and (S)-N-(2-benzoylphenyl)-1-(4-fluorobenzyl)-pyrrolidine-2-carboxamide and their NiII complexes of Schiff bases with glycine and alanine have been synthesized. The greater efficiency of the complexes in terms of faster reaction rates and stereoselectivities in the asymmetric synthesis of (S)-α-amino acids has also been demonstrated.

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

The influence of imine structure, catalyst structure and reaction conditions on the enantioselectivity of the alkylation of alanine methyl ester imines catalyzed by Cu(ch-salen)

Systematic variation of the substrate structure has shown that the most effective substrates for Cu(ch-salen)-catalyzed asymmetric enolate alkylation reactions carried out under phase-transfer conditions are the para-chlorophenyl imines of amino esters. T

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%.

Asymmetric PTC C-Alkylation Catalyzed by Chiral Derivatives of Tartaric Acid and Aminophenols. Synthesis of (R)- and (S)-α-Methyl Amino Acids

A new type of efficient chiral catalyst has been elaborated for asymmetric C-alkylation of CH acids under PTC conditions. Sodium alkoxides formed from chiral derivatives of tartaric acid and aminophenols (TADDOL's 2a-e and NOBIN's 3a-h) can be used as chiral catalysts in the enantioselective alkylation, as exemplified by the reaction of Schiffs bases la-e derived from alanine esters and benzaldehydes with active alkyl halides. Acid-catalyzed hydrolysis of the products formed in the reaction afforded (R)-α-methylphenylalanine, (R)-α-naphthylmethylalanine, and (R)-α-allylalanine in 61-93% yields and with ee 69-93%. The procedure could be successfully scaled up to 6 g of substrate 1b. When (S,S)-TADDOL or (R)-NOBIN are used, the (S)-amino acids are formed. A mechanism rationalizing the observed features of the reaction has been suggested.

Mag: A Cα-methylated, side-chain unsaturated α-amino acid. Introduction into model peptides and conformational preference

By a chemo-enzymatic approach we synthesized the chiral, C(α)- methylated α-amino acid Mag, characterized by a side-chain C(γ)=C(δ) bond. We also prepared a series of model peptides containing Mag in combination with Aib and Ala. All of the peptides were fully characterized and their conformational preference was determined in solution by FT-IR absorption and 1H NMR investigations. X-Ray diffraction analyses of L-Mag, a derivative and three peptides are also presented. We find that this C(α)-methylated α- amino acid is an excellent β-turn and 310-helix former. A peptide with two Mag residues one on top of the other after one complete turn of the 310- helix has been synthesized and characterized. 2000 Elsevier Science Ltd.

Chiral 3,6-dihydro-2H-1,4-oxazin-2-ones as alanine equivalents for the asymmetric synthesis of α-methyl α-amino acids (AMAAs) under mild reaction conditions

3,6-Dihydro-2H-1,4-oxazin-2-ones 1 act as very reactive chiral cyclic alanine equivalents and can be diastereoselectively alkylated or allylated using mild reaction conditions: potassium carbonate under phase-transfer catalysis (PTC) conditions when using activated alkyl halides, organic bases such as tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2- diazaphosphorine (BEMP) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) when using unactivated alkyl halides, and neutral Pd(0)-catalysis when allylic carbonates are used. In most cases, the diastereoselectivity under all these different reaction conditions is excellent although the reactions are always carried out at room temperature. Hydrolysis of the obtained alkylated or allylated oxazinones allows the preparation of enantiomerically enriched (S)- α-methyl α-amino acids (S)-AMAAs. The PTC and organic base methodologies have also been applied to the synthesis of (R)-α-methyl α-amino acids starting from (R)-alanine. When dihalides are used as electrophiles under PTC or BEMP conditions, a spontaneous N-alkylation also takes place giving bicyclic oxazinones, which can be hydrolyzed to enantiomerically pure cyclic (S)-AMAAs.

Enantioselective syntheses of 2-amino-4-fluoropent-4-enoic acids. Isosteres of asparagine

Diastereoselective alkylation of (R)-(+)-camphor-based glycine or alanine esterimines with 3-bromo-2-fluoropropene after hydrolytic deprotection gave (R)-(+)-2-amino-4-fluoropent-4-enoic acid with 38% overall yield and 90% ee, or (R)-(+)-2-amino-4-fluoro-2-methylpent-4-enoic acid (19% overall yield, 59% ee), respectively. Deprotection under drastic conditions was accompanied by hydrolysis of the fluorovinyl moiety to give (R)-(-)-2- amino-4-oxopentanoic acid hydrochloride with 28% overall yield and >95% ee. Ab initio calculations of acetamide and 2-fluoropropene as models for a primary amide or a fluorovinyl group despite of their different electronic structure show a similar electrostatic potential on the van der Waals surface suggesting their isosteric behavior.

Asymmetric alkylation catalyzed by chiral alkali metal alkoxides of TADDOL. Synthesis of α-methyl amino acids

It is shown that sodium alkoxides formed from (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethanol) ((R,R)-TADDOL) and some of its derivatives can be used as chiral catalysts for enantioselective alkylation of Schiff's bases derived from alanine with reactive alkyl halides. Acid hydrolysis of the reaction products affords (R)-α-methytphenyl-alanine, (R)-α-allylalanine, and (R)-α-methylnaphthylalanine in 61-93% yields and with ee 69-94%. When (S,S)-TADDOL is used, the (3)-amino acid is formed. A mechanism explaining the observed features of the reaction is proposed.