D-1-Naphthylalanine

Base Information

• Chemical Name: D-1-Naphthylalanine
• CAS No.: 78306-92-0
• Molecular Formula: C13H13NO2
• Molecular Weight: 215.252
• Hs Code.: 2922499990
• Mol file: 78306-92-0.mol

Synonyms:1-Naphthalenepropanoicacid, a-amino-, (R)-;3-(1-Naphthyl)-D-alanine;D-3-(1-Naphthyl)alanine;D-b-(1-Naphthyl)alanine;b-1-Naphthyl-D-alanine;H-D-1-Nal-OH;

Chemical Property of D-1-Naphthylalanine

Chemical Property:

• Vapor Pressure: 1.14E-08mmHg at 25°C
• Refractive Index: 1.678
• Boiling Point: 412.3 °C at 760 mmHg
• PKA: 2.21±0.30(Predicted)
• Flash Point: 203.2 °C
• PSA: 63.32000
• Density: 1.254 g/cm³
• LogP: 2.49450
• Storage Temp.: 2-8°C
• Solubility.: 2 M HCl: 50 mg/mL, clear, yellow

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2R)-2-Amino-3-(naphth-1-yl)propanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-(1-Naphthyl)-D-alanine is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Technology Process of D-1-Naphthylalanine

There total 9 articles about D-1-Naphthylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

(R)-3-Naphthalen-1-yl-2-((4S,5R)-2-oxo-4,5-diphenyl-oxazolidin-3-yl)-propionic acid benzyl ester (161633-96-1) → 3-(1-naphthyl)-D-alanine (78306-92-0,68798-79-8,7758-42-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; for 19h; under 3102.9 Torr;

DOI:10.1021/ja00097a020

Reference yield: 55.0%

(R)-2-Acetylamino-3-naphthalen-1-yl-propionic acid ethyl ester (136086-24-3) → 3-(1-naphthyl)-D-alanine (78306-92-0,68798-79-8,7758-42-1)

Guidance literature:

With hydrogenchloride; for 2h; Heating;

DOI:10.1016/0223-5234(91)90056-S

Reference yield:

2-amino-3-(1-naphthyl)propanoic acid (28095-56-9,68798-79-8,7758-42-1) → L-1-naphthylalanine (55516-54-6,68798-79-8,7758-42-1) + 3-(1-naphthyl)-D-alanine (78306-92-0,68798-79-8,7758-42-1)

Guidance literature:

With chiral stationary phase including isopropyl-functionalized CF₆; In methanol; acetic acid; triethylamine; acetonitrile; at 0 ℃; Purification / work up;

upstream raw materials:

(R)-2-Acetylamino-3-naphthalen-1-yl-propionic acid ethyl ester

(R)-3-Naphthalen-1-yl-2-((4S,5R)-2-oxo-4,5-diphenyl-oxazolidin-3-yl)-propionic acid benzyl ester

diethyl (N-acetylamino)[(1-naphthyl)methyl]malonate

2-Acetylamino-2-naphthalen-1-ylmethyl-malonic acid monoethyl ester

Downstream raw materials:

D-3-(1-naphthyl)alanine methylester

(S)-1-naphthylalanine methyl ester

N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-3-(1-naphthalenyl)-D-alanine

Refernces

• 1、 Rosini, Elena,Melis, Roberta,Molla, Gianluca,Tessaro, Davide,Pollegioni, Loredano. "Deracemization and Stereoinversion of α-Amino Acids by l-Amino Acid Deaminase". . p. 3773 - 3781. Retrieved 2017/11/13.
• 2、 Belokon, Yuri N,North, Michael,Churkina, Tatiana D,Ikonnikov, Nikolai S,Maleev, Victor I. "Chiral salen-metal complexes as novel catalysts for the asymmetric synthesis of α-amino acids under phase transfer catalysis conditions". . p. 2491 - 2498. Retrieved 2007/10/03.