(R)-2-Acetamido-3-(4-nitrophenyl)propanoic acid

Base Information

• Chemical Name: (R)-2-Acetamido-3-(4-nitrophenyl)propanoic acid
• CAS No.: 89615-73-6
• Molecular Formula: C11H12N2O5
• Molecular Weight: 252.227
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID40427555
• Nikkaji Number: J898.176K
• Wikidata: Q72434096
• Mol file: 89615-73-6.mol

Synonyms:89615-73-6;(R)-2-ACETAMIDO-3-(4-NITROPHENYL)PROPANOIC ACID;(2R)-2-acetamido-3-(4-nitrophenyl)propanoic acid;(R)-2-Acetamido-3-(4-nitrophenyl)propanoicacid;SCHEMBL11208510;DTXSID40427555;N-Acetyl-4-nitro-D-phenylalanine;SOPVYCYKWGPONA-SNVBAGLBSA-N;AKOS015914301;Nalpha -Acetyl-p-Nitro-D-Phenylalanine;EN300-18711498;(R)-alpha-(Acetylamino)-4-nitrobenzenepropionic acid

Chemical Property of (R)-2-Acetamido-3-(4-nitrophenyl)propanoic acid

Chemical Property:

• Vapor Pressure: 3.86E-13mmHg at 25°C
• Refractive Index: 1.579
• Boiling Point: 554.7 °C at 760 mmHg
• Flash Point: 289.3 °C
• PSA: 112.22000
• Density: 1.366 g/cm³
• LogP: 1.64070
• Storage Temp.: 2-8°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 252.07462149
• Heavy Atom Count: 18
• Complexity: 331

Purity/Quality:

99% ^*data from raw suppliers

(R)-2-acetamido-3-(4-nitrophenyl)propanoicacid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CC=C(C=C1)[N+](=O)[O-])C(=O)O
• Isomeric SMILES: CC(=O)N[C@H](CC1=CC=C(C=C1)[N+](=O)[O-])C(=O)O

Technology Process of (R)-2-Acetamido-3-(4-nitrophenyl)propanoic acid

There total 7 articles about (R)-2-Acetamido-3-(4-nitrophenyl)propanoic acid 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:

N-acetyl-4-nitro-DL-phenylalanine (62561-97-1) → 4-nitro-3-phenyl-L-alanine (949-99-5) + N-acetyl-4-nitro-D-phenylalanine (89615-73-6)

Guidance literature:

With lipase AS 'Amano'; at 35 ℃; for 24h; pH=6.5; enantioselective reaction; Enzymatic reaction;

DOI:10.1016/j.tetasy.2012.08.017

Reference yield:

4-nitrophenylalanine (1991-83-9,2922-40-9,56613-61-7,949-99-5) → 4-nitro-3-phenyl-L-alanine (949-99-5) + N-acetyl-4-nitro-D-phenylalanine (89615-73-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / water; N,N-dimethyl-formamide / 20 °C

2: lipase AS 'Amano' / 24 h / 35 °C / pH 6.5 / Enzymatic reaction

With lipase AS 'Amano'; triethylamine; In water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2012.08.017

Reference yield:

α-acetylamino-4-nitro-trans-cinnamic acid (93341-45-8) → N-acetyl-4-nitro-D-phenylalanine (89615-73-6)

Guidance literature:

With hydrogen; nonane>⁺; In methanol; at 25 ℃; for 0.166667h; under 760 Torr;

DOI:10.1021/ja970955q

upstream raw materials:

N-acetyl-4-nitro-DL-phenylalanine

α-acetylamino-4-nitro-trans-cinnamic acid

2-acetylamino-2-(4-nitrobenzyl)malonic acid diethyl ester

2-(N-acetylamino)-2-benzylpropanedioic diethyl ester

Downstream raw materials:

(R)-4-nitro-phenylalanine

N-acetyl-4-nitro-D-phenylalanine ethyl ester

4-nitro-D-phenylalanine ethyl ester; hydrochloride

Ac-p-NO2-D-Phe-Mel-OEt

Refernces

• 1、 Zhang, Fu-Yao,Kwok, Wai Him,Chan, Albert S.C.. "A comparison of the asymmetric hydrogenation catalyzed by rhodium complexes containing chiral ligands with a binaphthyl unit and those with a 5,5′,6,6′,7,7′,8,8′-octahydro-binaphthyl unit". . p. 2337 - 2342. Retrieved 2007/10/03.