Afalanine

Base Information

• Chemical Name: Afalanine
• CAS No.: 2901-75-9
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• Hs Code.: 2924299090
• European Community (EC) Number: 220-793-9
• NSC Number: 523830,45699,43242
• UNII: FFW2NGO18S
• DSSTox Substance ID: DTXSID3045697
• Nikkaji Number: J27.568I
• Wikidata: Q27109408
• NCI Thesaurus Code: C72682
• ChEMBL ID: CHEMBL134570
• Mol file: 2901-75-9.mol

Synonyms:N-acetylphenylalanine;N-acetylphenylalanine, (D)-isomer;N-acetylphenylalanine, (D,L)-isomer, 3H-labeled;N-acetylphenylalanine, (L)-isomer;N-acetylphenylalanine, (L)-isomer, 3H-labeled

Chemical Property of Afalanine

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 2.07E-05mmHg at 25°C
• Melting Point: 152.0 to 156.0 °C
• Refractive Index: 1.574
• Boiling Point: 453.9 °C at 760 mmHg
• PKA: 3.56±0.10(Predicted)
• Flash Point: 228.3 °C
• PSA: 66.40000
• Density: 1.199 g/cm³
• LogP: 1.20930
• Storage Temp.: Store at 0-5°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 207.08954328
• Heavy Atom Count: 15
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

N-Acetyl-DL-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CC=CC=C1)C(=O)O
• Uses: N-Acetyl-DL-phenylalanine is an antidepressant, used to prevent kidney damage.
• Therapeutic Function: Antidepressant

Technology Process of Afalanine

There total 54 articles about Afalanine 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: 100.0%

N-acetamido cinnamic acid (55065-02-6,64590-80-3,5469-45-4) → (R,S)-N-acetyl phenylalanine (2901-75-9)

Guidance literature:

With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In methanol; toluene; for 16h; under 15001.2 Torr; Product distribution; Ambient temperature; var. of ligand, pressure, asymmetric induction;

Reference yield: 100.0%

2-(N-acetylamino)cinnamic acid (55065-02-6,64590-80-3,5469-45-4) → (R,S)-N-acetyl phenylalanine (2901-75-9)

Guidance literature:

With hydrogen; S-MetHPdCl₂; In methanol; at 20 ℃; for 5h; under 750.06 Torr; Product distribution; other solvent, catalyst, time, reagent;

DOI:10.1007/BF00957088

Reference yield: 96.1%

5%-palladium-carbon + 2-methyl-4-benzylidene-5-oxazolone (41537-73-9) + sodium α-(acetylamino)cinnamate (100350-85-4) → (R,S)-N-acetyl phenylalanine (2901-75-9)

Guidance literature:

With hydrogenchloride; sodium hydroxide; In water; hydrogen;

upstream raw materials:

2-(N-acetylamino)cinnamic acid

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

Phenylalanine

acetic anhydride

Downstream raw materials:

N-acetyl-DL-phenylalanine-[2]naphthyl ester

(R)-N-acetylphenylalanin

(S)-2-acetylamino-3-phenylpropanoic acid

N-acetyl-phenylalanine-(2-carbamoyl-phenyl ester)

Refernces

• 1、 De Vries, Johannes G.,De Boer, Rene P.,Hogeweg, Marjo,Gielens, Esther E. C. G.. "Preparation of d,l-phenylalanine by amidocarbonylation of benzyl chloride". . p. 1842 - 1846. Retrieved 1996.
• 2、 Belokon',Bachurina,Tararov,Saporovskaya. "Mechanism of hydrolysis of azalactones catalyzed by a complex of Cu(II) with (S)-2-[(N-benzylpropyl)amino]benzaldoxime". . p. 422 - 429. Retrieved 1992.
• 3、 Sablong, Rafael,Van Der Vlugt, Jarl Ivar,Thomann, Ralf,Mecking, Stefan,Vogt, Dieter. "Disperse amphiphilic submicron particles as non-covalent supports for cationic homogeneous catalysts". . p. 633 - 636. Retrieved 2005.
• 4、 Snyder,Shekleton,Lewis. "-". . p. 310. Retrieved 1945.
• 5、 Knowles et al.. "". . p. 2567,2568. Retrieved 1975.
• 6、 Gheorghiu,Machado,Salinas-Martinez De Lecea,Gouygou,Roman-Martinez,Serp. "Chiral rhodium complexes covalently anchored on carbon nanotubes for enantioselective hydrogenation". . p. 7455 - 7463. Retrieved 2014.
• 7、 Chirik, Paul J.,Shevlin, Michael,Zhong, Hongyu. "Cobalt-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Carboxylic Acids by Homolytic H2 Cleavage". supporting information. . Retrieved 2020/03/13.
• 8、 Wende, Raffael C.,Seitz, Alexander,Niedek, Dominik,Schuler, S?ren M. M.,Hofmann, Christine,Becker, Jonathan,Schreiner, Peter R.. "The Enantioselective Dakin-West Reaction". supporting information. p. 2719 - 2723. Retrieved 2016/02/27.