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2577-48-2

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2577-48-2 Usage

General Description

Methyl L-prolinate is a chemical compound that falls under the category of organic compounds known as L-alpha-amino acids. As an organic compound, it is an ester derivative of the amino acid proline with a molecular formula of C7H13NO3. It typically appears as a clear, colorless liquid at room temperature. Methyl L-prolinate is most commonly used for research and development applications. It does not have any major industrial or commercial applications. As with all chemicals, it should be handled with care to avoid potential health and safety hazards.

Check Digit Verification of cas no

The CAS Registry Mumber 2577-48-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,7 and 7 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 2577-48:
(6*2)+(5*5)+(4*7)+(3*7)+(2*4)+(1*8)=102
102 % 10 = 2
So 2577-48-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H11NO2/c1-9-6(8)5-3-2-4-7-5/h5,7H,2-4H2,1H3

2577-48-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl (2S)-2-pyrrolidinecarboxylate

1.2 Other means of identification

Product number -
Other names Methyl L-prolinate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2577-48-2 SDS

2577-48-2Relevant articles and documents

Electron transfer through the hydrogen-bonded interface of a β-turn- forming depsipeptide

Williamson, David A.,Bowler, Bruce E.

, p. 10902 - 10911 (1998)

Hydrogen-bonding networks are believed to play an important role in electron-transfer pathways in a protein medium. A porphyrin-quinone donor- acceptor compound with a depsipeptide bridge which forms a β-turn has been synthesized to study hydrogen bond-mediated electron transfer. The placement of the donor and acceptor has been chosen to favor electron transfer through the hydrogen bond interface of the β-turn. Use of ester linkages also allows control of the hydrogen-bonding pattern within the β-turn-forming depsipeptide. Infrared spectroscopy in the amide A (NH stretch) and amide I (carbonyl stretch) regions indicates that the β-turn conformation is about 85% populated in dichloromethane and essentially completely disrupted in dimethyl sulfoxide at 296 K. The electron-transfer rate constant, k(et), was evaluated using the singlet excited-state lifetimes of the porphyrin in the presence and absence of an electron acceptor. The lifetimes were obtained using time-correlated single-photon-counting fluorescence spectroscopy. Very fast electron transfer (k(et) = (1.1 ± 0.1) x 109 s-1) was observed in the presence of the β-turn conformation. When the β-turn structure was disrupted using the solvent DMSO, electron transfer was no longer competitive with the intrinsic fluorescence emission. Analysis of the data in terms of Marcus theory and the pathway model for electronic coupling yielded a value for the hydrogen bond coupling decay factor, ε(hb), of 0.8 ± 0.4, which is of the same order of magnitude as the theoretically predicted value of 0.36.

Psychrophilin E, a new cyclotripeptide, from co-fermentation of two marine alga-derived fungi of the genus Aspergillus

Ebada, Sherif S.,Fischer, Thomas,Hamacher, Alexandra,Du, Feng-Yu,Roth, Yoen Ok,Kassack, Matthias U.,Wang, Bin-Gui,Roth, Eckhard H.

, p. 776 - 781 (2014)

Chemical investigation of the mycelial extract of a mixed culture of two marine alga-derived fungal strains of the genus Aspergillus has yielded one new cyclotripeptide, psychrophilin E (1), the recently reported oxepin-containing alkaloids, protuboxepin A (2) and oxepinamide E (3), together with three other polyketide derivatives (4-6). The chemical structure and relative and absolute configurations of psychrophilin E (1) were unambiguously established based on HRMS, 1D, 2D NMR and chiral-phase HPLC analysis of its hydrolysate. All the isolated compounds were assessed for their anti-proliferative activity against four different human cancer cell lines and some of them revealed selective activities. 2014

Diastereoselective hydrogenation of a tricyclic α,β -dehydrodipeptide

Kukula, Pavel,Prins, Roel

, p. 240 - 244 (2003)

An unsaturated diketopiperazine derivative with a tricyclic α, β-dehydrodipeptide structure was isolated as a reaction intermediate in the hydrogenation of pyrazine-2-(methyl-(S)-prolinecarboxamide). The diastereoselective hydrogenation of this dehydrodipeptide was studied using various noble metals (Pd, Pt, Rh, and Ru) supported on charcoal. The hydrogenation over Pd, Rh, and Ru catalysts proceeded with a high diastereoselectivity (71-79%), and the diastereomer with the (S)-configuration on both chiral carbon atoms was formed preferentially. The reaction rates and diastereoselectivities of the hydrogenation over the Pd, Rh, and Ru catalysts were similar, while the platinum catalyst was much less active and selective (48% d.e.). The obtained results were compared with those of the hydrogenation of pyrazine-2-(methyl-(S)-prolinecarboxamide); two different pathways for the hydrogenation of this molecule were suggested. In one path, cyclization already occurs after hydrogenation to the tetrahydropyrazine molecule, and in the other path cyclization occurs after full hydrogenation of the pyrazine molecule.

Synthesis and properties of novel chiral ionic liquids from L-proline

Gao, Hong-Shuai,Hu, Zhi-Guo,Wang, Jian-Ji,Qiu, Zhao-Fa,Fan, Feng-Qiu

, p. 521 - 525 (2008)

A novel class of chiral ionic liquids with chiral cations directly derived from natural l-proline has been synthesized and their physical properties such as melting point, thermal degradation, and specific rotation have been characterized. Further, their potential use in chiral recognition was demonstrated by studying interactions with racemic Mosher's acid salt. CSIRO 2008.

Conformational analysis and intramolecular interactions of l -proline methyl ester and its N -acetylated derivative through spectroscopic and theoretical studies

Braga, Carolyne B.,Ducati, Lucas C.,Tormena, Claudio F.,Rittner, Roberto

, p. 1748 - 1758 (2014)

This work reports a detailed study regarding the conformational preferences of l-proline methyl ester (ProOMe) and its N-acetylated derivative (AcProOMe) to elucidate the effects that rule their behaviors, through nuclear magnetic resonance (NMR) and infrared (IR) spectroscopies combined with theoretical calculations. These compounds do not present a zwitterionic form in solution, simulating properly amino acid residues in biological media, in a way closer than amino acids in the gas phase. Experimental 3JHH coupling constants and infrared data showed excellent agreement with theoretical calculations, indicating no variations in conformer populations on changing solvents. Natural bond orbital (NBO) results showed that hyperconjugative interactions are responsible for the higher stability of the most populated conformer of ProOMe, whereas for AcProOMe both hyperconjugative and steric effects rule its conformational equilibrium.

Diastereomeric atropisomers from a chiral diyne by cobalt(I)-catalyzed cyclotrimerization

Fischer, Fabian,Jungk, Phillip,Weding, Nico,Spannenberg, Anke,Ott, Holger,Hapke, Marko

, p. 5828 - 5838 (2012)

The reaction of new, chiral, proline-based naphthyl diynes with different nitriles through a key [2+2+2] cycloaddition reaction step catalyzed by Co I-olefin complexes under thermal and photochemical conditions gave diastereomeric atropisomers in good yield and nearly 1:1 ratios. Facile chromatographic separation of the naphthyl tetrahydroisoquinolines gave access to both pure and stable diastereomeric atropisomers. The deprotection and direct functionalization of the methyl-or methoxymethyl-protected 2-naphthyl position of the atropisomers were investigated. The configuration of the formed atropisomers was assigned from results of X-ray studies and circular dichroism spectroscopy.

Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts

Kervefors, Gabriella,Kersting, Leonard,Olofsson, Berit

supporting information, p. 5790 - 5795 (2021/03/08)

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

Stereoretentive N-Arylation of Amino Acid Esters with Cyclohexanones Utilizing a Continuous-Flow System

Ichitsuka, Tomohiro,Komatsuzaki, Shingo,Masuda, Koichiro,Koumura, Nagatoshi,Sato, Kazuhiko,Kobayashi, Shū

supporting information, p. 10844 - 10848 (2021/05/31)

The N-arylation of chiral amino acid esters with minimal racemization is a challenging transformation because of the sensitivity of the α-stereocenter. A versatile synthetic method was developed to prepare N-arylated amino acid esters using cyclohexanones as aryl sources under continuous-flow conditions. The designed flow system, which consists of a coil reactor and a packed-bed reactor containing a Pd(OH)2/C catalyst, efficiently afforded the desired N-arylated amino acids without significant racemization, accompanied by only small amounts of easily removable co-products (i. e., H2O and alkanes). The efficiency and robustness of this method allowed for the continuous synthesis of the desired product in very high yield and enantiopurity with high space-time yield (74.1 g L?1 h?1) and turnover frequency (5.9 h?1) for at least 3 days.

London Dispersion Interactions Rather than Steric Hindrance Determine the Enantioselectivity of the Corey–Bakshi–Shibata Reduction

Eschmann, Christian,Song, Lijuan,Schreiner, Peter R.

supporting information, p. 4823 - 4832 (2021/02/01)

The well-known Corey–Bakshi–Shibata (CBS) reduction is a powerful method for the asymmetric synthesis of alcohols from prochiral ketones, often featuring high yields and excellent selectivities. While steric repulsion has been regarded as the key director of the observed high enantioselectivity for many years, we show that London dispersion (LD) interactions are at least as important for enantiodiscrimination. We exemplify this through a combination of detailed computational and experimental studies for a series of modified CBS catalysts equipped with dispersion energy donors (DEDs) in the catalysts and the substrates. Our results demonstrate that attractive LD interactions between the catalyst and the substrate, rather than steric repulsion, determine the selectivity. As a key outcome of our study, we were able to improve the catalyst design for some challenging CBS reductions.

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