37440-01-0

Basic information

• Product Name: (R)-N-Acetyl-2-naphthylalanine
• Synonyms: (R)-N-ACETYL-2-NAPHTHYLALANINE 95% (98% E.E.);(R)-N-Acetyl-2-naphthylalanine, ee:95%;(R)-N-Acetyl-2-naphthylalanineN-Acetyl-D-2-naphthylalanine;(R)-N-Acetyl-2-naphthylalanine, (98% ee);Ac-2-D-Nal-OH;Acetyl-3-(2-naphthyl)-D-alanine≥ 98% (HPLC);AC-D-ALA(2-NAPHTHYL)-OH;AC-D-2-NAL-OH
• CAS NO: 37440-01-0
• Molecular Formula: C₁₅H₁₅NO₃
• Molecular Weight: 257.28
• Mol File: 37440-01-0.mol

Chemical Properties

• Boiling Point: 400.53°C (rough estimate)
• Flash Point: 282.461 °C
• Appearance: Off-white to white/Powder
• Density: 1.1391 (rough estimate)
• Vapor Pressure: 1.21E-12mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: 2-8°C
• PKA: 3.59±0.30(Predicted)
• CAS DataBase Reference: (R)-N-Acetyl-2-naphthylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-Acetyl-2-naphthylalanine(37440-01-0)
• EPA Substance Registry System: (R)-N-Acetyl-2-naphthylalanine(37440-01-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 37440-01-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Biochemical Research:
(R)-N-Acetyl-2-naphthylalanine is used as a chiral building block for the development of new pharmaceutical compounds and as a tool in biochemical research. Its specific configuration and naphthyl group provide unique binding properties that can be exploited in the design of novel drugs and the study of enzyme interactions.
Used in Enzyme Inhibition Studies:
(R)-N-Acetyl-2-naphthylalanine is used as an inhibitor in enzyme studies, specifically for the aromatic binding site of α-chymotrypsin. Its structure allows for the investigation of enzyme specificity and the development of new inhibitors targeting this binding site.
Used in Asymmetric Synthesis:
(R)-N-Acetyl-2-naphthylalanine is used as a key component in the asymmetric synthesis of new chiral compounds, such as cylindrically chiral and air-stable ferrocenyldiphosphines. Its R-configuration plays a crucial role in the stereochemistry of the synthesized products.
Used in Catalysis:
(R)-N-Acetyl-2-naphthylalanine is used in the field of catalysis, particularly in rhodium-catalyzed asymmetric hydrogenation. Its chiral nature and unique structural features contribute to the enantioselectivity and efficiency of the catalytic process.

InChI:InChI=1/C15H15NO3/c1-10(17)16-14(15(18)19)9-11-6-7-12-4-2-3-5-13(12)8-11/h2-8,14H,9H2,1H3,(H,16,17)(H,18,19)/p-1/t14-/m1/s1

Upstream product

• 1353886-59-5 ethyl 2-(hydroxyimino)-3-(naphthalen-3-yl)propanoate 
• 14108-60-2 2-amino-3-(2-naphthyl)propanoic acid 
• 108-24-7 acetic anhydride 
• 37447-33-9 acetylamino-[2]naphthylmethyl-malonic acid diethyl ester 
• 37439-99-9 (RS)-N-acetyl-2-naphthylalanine 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 136015-51-5 (R)-2-Acetylamino-3-naphthalen-2-yl-propionic acid ethyl ester 

Downstream Products

• 6960-34-5 L-3-(2-naphthyl)alanine 
• 76985-09-6 (R)-2-naphthylalanine 
• 292141-31-2 Ac-D-Nal2-D-Cpa-D-Pal-Gly-Arg-Pro-D-Ala-NH2 
• 292141-25-4 Ac-D-Nal₂-D-Cpa-D-Pal-D-Ala-Lys-Pro-D-Ala-NH₂ 
• 292141-31-2 Ac-D-Nal2-D-Cpa-D-Pal-Gly-D-Arg-Pro-D-Ala-NH2 

Relevant articles and documents

The Enantioselective Dakin-West Reaction

Here we report the development of the first enantioselective Dakin-West reaction, yielding α-acetamido methylketones with up to 58 % ee with good yields. Two of the obtained products were recrystallized once to achieve up to 84 % ee. The employed methylimidazole-containing oligopeptides catalyze both the acetylation of the azlactone intermediate and the terminal enantioselective decarboxylative protonation. We propose a dispersion-controlled reaction path that determines the asymmetric reprotonation of the intermediate enolate after the decarboxylation.

Preparation of cross-linked enzyme aggregates of l-aminoacylase via co-aggregation with polyethyleneimine

l-Aminoacylase from Aspergillus melleus was co-aggregated with polyethyleneimine and subsequently cross-linked with glutaraldehyde to obtain aminoacylase-polyethyleneimine cross-linked enzyme aggregates (termed as AP-CLEA). Under the optimum conditions, AP-CLEA expressed 74.9% activity recovery and 81.2% aggregation yield. The said method of co-aggregation and cross-linking significantly improved the catalytic stability of l-aminoacylase with respect to temperature and storage. AP-CLEA were employed for enantioselective synthesis of three unnatural amino acids (namely: phenylglycine, homophenylalanine and 2-naphthylalanine) via chiral resolution of their ester-, amide- and N-acetyl derivatives. The enantioselectivity of AP-CLEA was the highest for hydrolysis of amino acid amides; was moderate for hydrolysis of N-acetyl amino acids and was the least for hydrolysis of amino acid esters. Furthermore, AP-CLEA were found to retain more than 92% of the initial activity after five consecutive batches of (RS)-homophenylalanine hydrolysis suggesting an adequate operational stability of the biocatalyst.

Convenient method for reduction of C-N double bonds in oximes, imines, and hydrazones using sodium Borohydride-Raney ni system

(Chemical Equation Presented) A practical method has been developed for reduction of C-N double bond in oximes, imines, and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution, and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic or aromatic amines and its analogs. Copyright Taylor & Francis Group, LLC.

CHIRAL PHOSPHORUS COMPOUNDS

The present invention provides P-chiral compounds of general formula (II) and (III): wherein at least one of R21, R25, R26 and R30 is independently selected from C1-4 alkyl, CF3, C1-4 alkoxy, phenyl and benzyloxy and the remaining substituents selected from R21, R25, R26 and R30 are hydrogen; at least one of R22, R24, R27 and R29 are independently selected from C1-4 alkyl, CF3, C1-4 alkoxy, phenyl and benzyloxy and the remaining substituents selected from R22, R24, R27 and R29 are hydrogen; and R23 and R28 are independently selected from hydrogen, C1-4 alkyl, CF3, C1-4 alkoxy, phenyl and benzyloxy; Formula (III): wherein at least one of R21, R25, R26 and R30 is independently selected from phenyl and benzyloxy and the remaining substituents selected from R21, R25, R26 and R30 are hydrogen; and R22, R23, R24, R27, R28 and R29 are independently selected from hydrogen, C1-4 alkyl, CF3, C1-4 alkoxy, phenyl and benzyloxy.wherein at least one of R21, R25, R26 and R30 is independently selected from phenyl and benzyloxy and the remaining substituents selected from R21, R25, R26 and R30 are hydrogen; and R22, R23, R24, R27, R28 and R29 are independently selected from hydrogen, C1-4 alkyl, CF3, C1-4 alkoxy, phenyl and benzyloxy.

A chiral 1,2-bisphospholane ligand with a novel structural motif: Applications in highly enantioselective Rh-catalyzed hydrogenations

TangPhos (1) is a highly efficient and practical ligand for asymmetric hydrogenations. High enantioselectivities and turnover numbers were observed in the Rh-catalyzed hydrogenation of α-(acylamino) acrylic acids and α-arylenamides.

A versatile modular approach to new chiral C2-symmetrical ferrocenyl ligands: Highly enantioselective Rh-catalyzed hydrogenation of α- acetamidoacrylic acid derivatives

An easy, efficient, flexible modular synthesis of a new family of chiral C2-symmetrical ferrocenyl diphosphines (FERRIPHOS) is described. These new ligands gave high enantioselectivities (up to 99.4% ee) in the rhodium- catalyzed hydrogenation of different enamide derivatives.

Asymmetric synthesis of a new cylindrically chiral and air-stable ferrocenyldiphosphine and its application to rhodium-catalyzed asymmetric hydrogenation

A novel, cylindrically chiral air-stable ferrocenyldiphosphine ligand has been synthesized and its rhodium complexes have been applied to asymmetric hydrogenation. High reactivity and selectivity have been realized in hydrogenation of various dehydroamino acid derivatives.