122022-98-4

Basic information

• Product Name: 2- Amino-3-cyclopentene-1-carboxylic acid
• Synonyms: 2- Amino-3-cyclopentene-1-carboxylic acid;3-Cyclopentene-1-carboxylicacid,2-amino-(9CI);(1R)-2β-Amino-3-cyclopentene-1β-carboxylic acid
• CAS NO: 122022-98-4
• Molecular Formula: C6H9NO2
• Molecular Weight: 127.14116
• Product Categories: AMINOACID
• Mol File: 122022-98-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2- Amino-3-cyclopentene-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2- Amino-3-cyclopentene-1-carboxylic acid(122022-98-4)
• EPA Substance Registry System: 2- Amino-3-cyclopentene-1-carboxylic acid(122022-98-4)

Safety Data

• Hazardous Substances Data: 122022-98-4(Hazardous Substances Data)

Usage

Structure

Cyclic amino acid It contains a cyclopentene ring (a five-carbon ring with double bonds between two of the carbons) and an amino group (-NH2) attached to one of the carbons, as well as a carboxylic acid group (-COOH) attached to another carbon.

Functional groups

Amino group, Carboxylic acid group The presence of these two functional groups imparts both basic and acidic properties to the compound, making it amphoteric.

Role in biosynthesis

Involvement in the production of natural products and pharmaceuticals 2-Amino-3-cyclopentene-1-carboxylic acid is a precursor or building block in the synthesis of certain biologically active compounds, including some natural products and pharmaceuticals.

Potential applications

Drug development Researchers are interested in the unique structure of 2-Amino-3-cyclopentene-1-carboxylic acid for its potential use in the development of new drugs, possibly due to its ability to influence biological processes or interact with other molecules.

Research interest

Synthesis and properties of organic compounds The structure of 2-Amino-3-cyclopentene-1-carboxylic acid makes it an interesting subject for researchers studying organic chemistry, particularly in terms of its synthesis, reactivity, and potential applications in various fields.

Upstream product

• 97911-48-3 (+/-)-6-azabicyclo[3.2.0]hept-3-en-7-one 
• 63838-48-2 6-Azabicyclo<3.2.0>hept-3-en-7-one 
• 542-92-7 cyclopenta-1,3-diene 

Relevant articles and documents

Synthesis of novel isoxazoline-fused cyclic β-amino esters by regio- and stereo-selective 1,3-dipolar cycloaddition

Isoxazoline-fused 2-aminocyclopentanecarboxylate derivatives were regio- and stereo-selectively synthesized by nitrile oxide 1,3-dipolar cycloaddition to cis- or trans-ethyl-2-aminocyclopent-3-enecarboxylates. The compounds were prepared in enantiomerical

Enantiomeric discrimination of cyclic β-amino acids using (18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent

(18-Crown-6)-2,3,11,12-tetracarboxylic acid is an excellent chiral NMR solvating agent for cyclic β-amino acids with cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, bicyclo[2.2.1]heptane, and bicyclo[2.2.1]heptene rings. The crown ether was added to the neutral β-amino acids in methanol-d4. A neutralization reaction between the crown ether and β-amino acid forms the ammonium ion needed for favorable association. Enantiomeric discrimination of the two hydrogen atoms α to the amine and carboxylic acid moieties of the β-amino acid was observed with every substrate studied. Trends in the order of the enantiomeric discrimination of certain hydrogen atoms for substrates of similar structures correlate with the absolute configuration.

A selective synthesis of fluorinated cispentacin derivatives

A facile selective method has been developed for the synthesis of new fluorine-containing cispentacin stereoisomers. Mono- and difluorinated cispentacin derivatives were synthetized from a bicyclic β-lactam in five or six steps involving a regio- and stereoselective hydroxylation through iodooxazoline formation, followed by deoxygenation by fluorination. Starting from an enantiomerically pure bicyclic β-lactam obtained by enzymatic resolution of the racemic compound, an enantiodivergent procedure allowed the preparation of both dextro- and levorotatory difluorinated cispentacins. Mono- and difluorinated cispentacin derivatives were synthetized from a bicyclic β-lactam in five or six steps. An enantiodivergent procedure allowed the preparation of both dextro- and levorotatory difluorinated cispentacins. Copyright

Nucleoside analogues of purine with a 1,2-disubstituted cyclopentene ring

One, two-disubstituted carbonucleoside analogues of purine with unsaturated carbocyclic were synthesized by construction of the heterocyclic base about the primary amino group of the amino alcohol 4 intermediate, which was also synthesized in good yield starting from cyclopentadiene.

Novel functionalized cispentacin derivatives. Synthesis of 1,2,3-triazole-substituted 2-aminocyclopentanecarboxylate stereoisomers

Four 1,2,3-triazole-substituted ethyl 2-amino-3-hydroxycyclopentanecarboxylate diastereomers (3,4-disubstituted cispentacins) with a cyclopentane skeleton were prepared in enantiomerically pure form from racemic β-lactam 7 via enzymatic ring opening, epoxidation and selective ring opening of the oxirane ring with sodium azide. The formation of the 1,2,3-triazole ring system involved click chemistry: 1,3-dipolar cycloaddition of the corresponding 4-substituted azidocarboxylates with diethyl acetylenedicarboxylate.

Advanced procedure for the enzymatic ring opening of unsaturated alicyclic β-lactams

Enantiopure β-amino acids 1a-4a and β-lactams 1b-4b were prepared simultaneously through the lipolase-catalysed enantioselective ring opening of unsaturated racemic β-lactams (±)-1-(±)-4. High enantioselectivities (E>200) were observed when the reactions

Stereo- and regiocontrolled synthesis of highly functionalized cyclopentanes with multiple chiral centers

The synthesis of some highly substituted three-dimensional cyclopentanes with multiple chiral centers and with high regiochemical and stereochemical diversity has been accomplished starting from cyclopentadiene-derived aminocyclopentenecarboxylic acids. The small-molecular design consisted of stereo- and regiocontrolled functionalization of the starting cyclopentene β- and γ-amino acids through oxirane formation/oxirane opening and afforded regio- and diastereoisomers of orthogonally protected aminocyclopentanecarboxylates.

High-Performance Liquid Chromatographic Enantioseparation of Cyclic β-Amino Acids on Zwitterionic Chiral Stationary Phases Based on Cinchona Alkaloids

Stereoselective high-performance liquid chromatographic separations of eight sterically constrained cyclic β-amino acid enantiomer pairs were carried out using the newly developed Cinchona alkaloid-based zwitterionic chiral stationary phases Chiralpak ZWIX(+) and ZWIX(-). The effects of the mobile phase composition, the nature and concentrations of the acid and base additives, the counterions and temperature on the separations were investigated. The changes in standard enthalpy, Δ(ΔH°), entropy, Δ(ΔS°), and free energy, Δ(ΔG°), were calculated from the linear van't Hoff plots derived from the ln α vs. 1/T curves in the studied temperature range (10-50°C). The values of the thermodynamic parameters depended on the nature of the selectors and the structures of the analytes. Unusual temperature behavior was observed on the ZWIX(-) column: decreased retention times were accompanied by increased separation factors with increasing temperature. On the ZWIX(+) column only enthalpically, whereas on the ZWIX(-) column both enthalpically and entropically driven separations were observed. The elution sequence was determined in all cases and was observed to be the opposite on ZWIX(+) and on ZWIX(-). Chirality 27:563-570, 2015.

A de Novo stereocontrolled approach to syn- and anti-disubstituted acyclic β2,3-amino acid enantiomers

The stereocontrolled syntheses of functionalized acyclic β2,3-amino acid derivatives in enantiomerically pure form were performed by starting from enantiopure cis- and trans-2-aminocyclopent-3- enecarboxylates, which were derived from a racemic bicyclic β-lactam. The synthetic strategy involves the stereoselective dihydroxylaton of the C-C double bond of the cyclopentene β-amino esters. The subsequent NaIO 4-mediated ring cleavage affords dialdehyde intermediates that undergo functionalization by a Wittig reaction. The stereocontrolled syntheses of functionalized acyclic β2,3-amino acid derivatives in enantiomerically pure form have been performed in five steps by starting from enantiopure cis- and trans-2-aminocyclopent-3-enecarboxylates, which were derived from a racemic bicyclic β-lactam. Copyright

A de Novo Stereocontrolled Approach to syn- and anti-Disubstituted Acyclic β2,3-Amino Acid Enantiomers

The stereocontrolled syntheses of functionalized acyclic β2,3-amino acid derivatives in enantiomerically pure form were performed by starting from enantiopure cis- and trans-2-aminocyclopent-3-enecarboxylates, which were derived from a racemic bicyclic β-lactam. The synthetic strategy involves the stereoselective dihydroxylaton of the C-C double bond of the cyclopentene β-amino esters. The subsequent NaIO4-mediated ring cleavage affords dialdehyde intermediates that undergo functionalization by a Wittig reaction.