64191-14-6

Basic information

• Product Name: (1S,2R)-2-Aminocyclopentanecarboxylic acid
• Synonyms: Cyclopentanecarboxylic acid, 2-amino-, (1S,2R)- (9CI);(1S,2R)-2-AMINO-CYCLOPETANECARBOXYLIC ACID ;(+)-Cispentacin.;(1S,2R)-2-Aminocyclopentanecarboxylic acid;(1S)-2α-Amino-1α-cyclopentanecarboxylic acid;(1S)-2α-Aminocyclopentane-1α-carboxylic acid;(1S,2R)-2α-Aminocyclopentane-1α-carboxylic acid;(1α)-2α-Aminocyclopentanecarboxylic acid
• CAS NO: 64191-14-6
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• Product Categories: AMINOACID
• Mol File: 64191-14-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 218-219 °C (sublm)(Solv: water (7732-18-5); acetone (67-64-1))
• Boiling Point: 264.72 °C at 760 mmHg
• Flash Point: 113.899 °C
• Appearance: /
• Density: 1.19 g/cm³
• PKA: 3.87±0.20(Predicted)
• CAS DataBase Reference: (1S,2R)-2-Aminocyclopentanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-2-Aminocyclopentanecarboxylic acid(64191-14-6)
• EPA Substance Registry System: (1S,2R)-2-Aminocyclopentanecarboxylic acid(64191-14-6)

Safety Data

• Hazardous Substances Data: 64191-14-6(Hazardous Substances Data)

Usage

General Description

(1S,2R)-2-Aminocyclopentanecarboxylic acid is a chemical compound that consists of a cyclopentane ring with an amino and carboxylic acid group attached. It is an unnatural amino acid and a conformationally constrained analogue of proline. The compound has a chiral center at carbon 1, with the S and R enantiomers occurring in equal amounts. (1S,2R)-2-Aminocyclopentanecarboxylic acid is not commonly found in nature, but it is used in laboratory research for the synthesis of peptides and as a building block in organic chemistry. It may also have potential applications in the field of medicinal chemistry for the development of biologically active compounds.

Upstream product

• 136315-70-3 (±)-cis-2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid 
• 163705-84-8 (1S,2R,αR)-2--1-(carbobenzyloxy)cyclopentane 
• 186249-66-1 (1S,2R)-2-phthalimidocyclopentane-1-carboxylic acid 
• 420123-97-3 (-)-(1S,2R)-N-benzyl-2-amino-cyclopentane-1-carboxylic acid 
• 50789-30-5 5,5-dimethoxypentanal 
• 420123-95-1 (+)-2-(5,5-dimethoxy-pentylidene)-[1S,3S]-1,3-dioxo-dithiane 
• 420123-96-2 (-)-4-aza-3-oxa-4-benzyl-2-spiro(1',3'-dithiane-[1'S,3'S]-1',3'-dioxo)-[5R,9S]-bicyclo[3.3.0] octane 
• 163705-82-6 2--amino-1-carbobenzoxycyclopentene 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 1883-85-8 trans-2-(hydroxymethyl)cyclopentanol 
• 186249-59-2 (1S,2R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclopentanol 
• 186249-65-0 2-((1R,2S)-2-Hydroxymethyl-cyclopentyl)-isoindole-1,3-dione 
• 186249-62-7 2-[(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclopentyl]-isoindole-1,3-dione 
• 1442488-67-6 benzyl (3R,3aS,6aR)-3-hydroxyhexahydro-1H-cyclopenta[c]isoxazole-1-carboxylate 

Downstream Products

• 958227-67-3 (1S,2R)-2-(5-bromo-2-{4-[methyl-(1-methyl-piperidin-4-yl)-carbamoyl]-phenylamino}-pyrimidin-4-ylamino)-cyclopentanecarboxylic Acid 
• 137170-89-9 (1S,2R)-2-((tert-butoxycarbonyl)amino)cyyclopentane-1-carboxylic acid 

Relevant articles and documents

Stereoselective organocatalytic approach to α,β-disubstituted- β-amino acids: A short enantioselective synthesis of cispentacin

α-Branched α,β-unsaturated aldehydes have been tested in the organocatalytic tandem Michael addition/cyclization with N-(benzyloxycarbonyl)hydroxylamine, a reaction which until now has been restricted to α-unsubstituted enals. Starting from cyclopentene-2- carbaldehyde, and using diphenylprolinol trimethylsilyl ether as a chiral amine catalyst, this approach has led to the development of a practical, high yielding (93-98 % overall yield, three steps), and highly enantioselective (up to 98:2 er) route to the cyclic β-amino acid cispentacin, which compares favourably with previously described asymmetric syntheses of this biologically active natural product. When using acyclic α-branched α,β-unsaturated aldehydes as substrates, the reaction yields depend on the substitution pattern of the aldehydes, and mixtures of cis- and trans-isomers are obtained. Nevertheless, this strategy has proved to be successful in some instances, and (3R,4R)-benzyl 3-ethyl-4-methyl-5-oxoisoxazolidin-2-carboxylate could be obtained in 70 % overall yield (two steps) from the reaction of 2-ethylcrotonaldehyde and N-(benzyloxycarbonyl)hydroxylamine under catalysis with diphenylprolinol trimethylsilyl ether, and with high enantiomeric purity (99:1 er). The organocatalytic tandem Michael addition/cyclization of cyclopentene-2-carbaldehyde with N-Cbz-hydroxylamine, using diphenylprolinol TMS ether as a chiral amine catalyst, gives a practical, high yielding, and highly enantioselective route to the cyclic β-amino acid cispentacin. Acyclic α-branched enals give variable results in the same reaction, depending on the substitution pattern. Copyright

An improved synthesis of enantiopure β-amino acids

An improved method for the preparation of both the enantiopure β-amino acids is presented. The diastereomer benzyl β-amino esters, obtained by stereoselective reduction of β-enamino esters, were separated and hydrogenolyzed to the free enantiopure β-amino acids.

Chemoenzymatic synthesis of both enantiomers of cispentacin

Based on the lipase-catalysed kinetic resolution of the silyloxyalcohol (1RS,2SR)-5 by transesterification with vinyl acetate in the presence of lipase from Pseudomonas cepacia a synthesis of both enantiomers of the β-amino acid cispentacin (1R,2S)-1 and (1S,2R)-1 using simple functional group interconversions is described.