16820-25-0

Basic information

• Product Name: (S)-2-AMINO-2-METHYL-4-PENTENOIC ACID
• Synonyms: ALPHA-ALLYL-L-ALA;(S)-ALPHA-METHYL-ALLYLGLYCINE;-Allyl-L-Ala;A-ALLYL-L-ALA ;3-Butenoicacid,2-amino-2-methyl-,(2S)-(9CI);(2S)-2-Amino-2-methyl-3-butenoic acid;(2S)-(9CI)
• CAS NO: 16820-25-0
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 129.16
• Product Categories: GLYCINESCAFFOLD
• Mol File: 16820-25-0.mol

Chemical Properties

• Boiling Point: 245.3 °C at 760 mmHg
• Flash Point: 102.1 °C
• Appearance: /
• Density: 1.101 g/cm³
• Vapor Pressure: 0.00946mmHg at 25°C
• Refractive Index: 1.485
• 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(16820-25-0)
• EPA Substance Registry System: (S)-2-AMINO-2-METHYL-4-PENTENOIC ACID(16820-25-0)

Safety Data

• Hazardous Substances Data: 16820-25-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
(S)-2-AMINO-2-METHYL-4-PENTENOIC ACID is used as a synthetic intermediate for the creation of complex organic molecules, leveraging its unique structural features and reactivity.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (S)-2-AMINO-2-METHYL-4-PENTENOIC ACID is utilized as a building block for the development of new drugs, given its potential to contribute to the synthesis of bioactive compounds.
Used in Biological Activities and Therapeutic Applications:
While further investigation is required, (S)-2-AMINO-2-METHYL-4-PENTENOIC ACID may have potential applications in biological activities and therapeutics, suggesting its use as a compound of interest for research into new treatments and medicinal agents.

InChI:InChI=1/C5H9NO2/c1-3-5(2,6)4(7)8/h3H,1,6H2,2H3,(H,7,8)/t5-/m0/s1

Upstream product

• 16820-23-8 2,4-dimethyl-4-vinyl-4H-oxazol-5-one 
• 151074-94-1 (+)-(2S)-Methyl 4,4-dibromo-2-methyl-2-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>-3-butenoate 
• 151074-90-7 (+)-(2S)-Methyl 2-methyl-2-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>buten-3-oate 
• 314774-36-2 (4S,5R)-4-Methyl-2-phenyl-5-phenylselanylmethyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 314774-43-1 (E)-(S)-2-Benzoylamino-2-methyl-4-phenylselanyl-but-3-enoic acid methyl ester 
• 151074-95-2 (S)-4-Bromo-2-methyl-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-but-3-ynoic acid 
• 121704-28-7 N-Methoxyacetyl-α-methyl-α-vinylglycine 

Downstream Products

• 1015251-57-6 (S)-2-(benzyloxycarbonylamino)-2-methylbut-3-enoic acid 

Relevant articles and documents

One-Pot Vinylation of Azlactones: Fast Access to Enantioenriched α-Vinyl Quaternary Amino Acids

We report a fast one-pot protocol for the direct vinylation of azlactones [oxazol-5-(4H)-ones] by using as a key step an aldol addition with 2-(phenylselenenyl)acetaldehyde followed by dehydroxyselenation. The acid hydrolysis of the oxazolone ring gave the desired fully deprotected α-vinyl quaternary α-amino acids in almost quantitative yields. An enantioselective variant of the method was also developed by using catalytic chiral bases. The use of Sharpless ligand (DHQD)2PHAL produced the final quaternary amino acids in good overall yields (62–78 %) and with ee values up to 86 %. Scaling up the optimized protocol to gram quantities did not affect the yields and ee values. We also demonstrated that the vinyl moiety installed onto the oxazolone ring can be exploited as a handle for the attachment of aryl groups through a Heck coupling reaction.

Amino alcohol derivatives

Compounds of formula (I) which exhibit excellent immune suppression activity, pharmacologically acceptable salts thereof, esters thereof or other derivatives: wherein R1 and R2 are a hydrogen atom, an amino protecting group; R3 is a hydrogen atom, a hydroxy protecting group; R4 is a lower alkyl group; n is an integer from 1 to 6; X is an ethylene group; Y is a C1-C10 alkylene group, a C1-C10 alkylene group substituted with 1 to 3 substituents selected from substituent group a and b; R5 is an aryl group; R6 and R7 are a hydrogen atom, a group selected from substituent group a; with the proviso when R5 is a hydrogen atom, Y is not a single bond or a straight chain C1-C10 alkylene group.

Asymmetric Synthesis of α-Alkyl-α-amino Acids from Chromium-Carbene-Complex-Derived β-Lactams

Optically active bicyclic β-lactam 3 was synthesized by photolysis of optically active oxazolidine carbene chromium complex 1 with oxazine 2.Conversion of the oxazolidine to the oxazolidinone gave a bicyclic β-lactam readily α-alkylated.Cleavage of the alkylated β-lactam gave optically active ester aldehyde 7, which was converted to a number of optically active α-alkyl-α-amino acids.These include (R)-α-methylserine, (S)-α-methylglutamic acid, (S)-α-methylornithine, (S)-vinylalanine, (S)-ethynylalanine, and (S)-2-methyl-2,3-diaminopropionic acid.

Kinetic Resolution of Unnatural and Rarely Occuring Amino Acids: Enantioselective Hydrolysis of N-Acyl Amino Acids Catalyzed by Acylase I

Acylase I (aminoacylase; N-acylamino-acid amidohydrolase, EC 3.5.1.14, from porcine kidney and the fungus Aspergillus) is broadly applicable enzymatic catalyst for the kinetic resolution of unnatural and rarely occuring α-amino acids.Its enantioselectivity for the hydrolysis of N-acyl L-α-amino acids is nearly absolute, yet it accepts substrates having a wide range of structure and functionality.This paper reports the initial rates of enzyme-catalyzed hydrolysis of over 50 N-acyl amino acids and analogues, the stabilities of the enzymes in aqueous and aqueous/organic solutions, and the effects of different acyl groups and metal ions on the rates of enzymatic hydrolysis.Eleven α-amino and α-methyl α-amino acids were resolved on a 2-29-g scale.Crude L- and D-amino acid products had generally >90percent ee.The utility of resolved amino acids as chiral synthons was illustrated by the preparation of (R)- and (S)-1-butene oxide and the diastereoselective (cis:trans, 7-8:1) iodolactonization of three 2-amino-4-alkenoic acid derivatives.

Methionine as Precursor for the Enantioselective Synthesis of α-Branched Vinylglycines and of Other Amino Acids

Methionine is converted by previously published methods into the diastereoisomerically pure 3-thiabutyl-substituted oxazolidinone (7) and imidazolidinones 5 and 6.An X-ray crystal structure determination of cis-3-benzoyl-2-(tert-butyl)-4-(3-thiabutyl)oxaz