(S)-N-Acetyl-2-naphthylalanine

Base Information

• Chemical Name: (S)-N-Acetyl-2-naphthylalanine
• CAS No.: 37439-99-9
• Molecular Formula: C15H15NO3
• Molecular Weight: 257.289
• Hs Code.: 2924299090
• UNII: 21A9PLE39M
• Nikkaji Number: J1.359.528C
• Mol file: 37439-99-9.mol

Synonyms:37439-99-9;(S)-N-ACETYL-2-NAPHTHYLALANINE;Ac-2-Nal-OH;(S)-2-Acetamido-3-(naphthalen-2-yl)propanoic acid;N-Acetyl Naphthylalanine;(2S)-2-acetamido-3-naphthalen-2-ylpropanoic acid;21A9PLE39M;N-Acetyl-3-(2-naphthyl)-L-alanine;(2S)-2-ACETAMIDO-3-(NAPHTHALEN-2-YL)PROPANOIC ACID;UNII-21A9PLE39M;Oprea1_506025;SCHEMBL607214;N-Acetyl-3-naphth-2-yl-L-alanine;MFCD03094597;WS-01926;CS-0276627;D86557;EN300-25598806;2-Naphthalenepropanoic acid, alpha-(acetylamino)-, (alphaS)-;2-NAPHTHALENEPROPANOIC ACID, .ALPHA.-(ACETYLAMINO)-, (.ALPHA.S)-

Chemical Property of (S)-N-Acetyl-2-naphthylalanine

Chemical Property:

• Vapor Pressure: 1.21E-12mmHg at 25°C
• Melting Point: 185-186 °C
• Refractive Index: 1.62
• Boiling Point: 530.7 °C at 760 mmHg
• Flash Point: 274.8 °C
• PSA: 66.40000
• Density: 1.243 g/cm³
• LogP: 2.36250
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 257.10519334
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

99% ^*data from raw suppliers

Ac-2-Nal-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CC2=CC=CC=C2C=C1)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CC1=CC2=CC=CC=C2C=C1)C(=O)O

Technology Process of (S)-N-Acetyl-2-naphthylalanine

There total 17 articles about (S)-N-Acetyl-2-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: 100.0%

(Z)-2-acetamido-3-(naphthalen-2-yl)acrylic acid → (S)-N-acetyl-3-(2-naphthyl)alanine (37439-99-9)

Guidance literature:

With hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; triethylamine; (2R,2'R)-bis(diphenylphosphino)-(1R,1'R)-dicyclopentane; In tetrahydrofuran; at 20 ℃; for 24h; under 750.075 Torr;

Reference yield: 98.0%

2-Acetylamino-3-naphthalen-2-yl-propionic acid ethyl ester (172214-89-0) → (S)-N-acetyl-3-(2-naphthyl)alanine (37439-99-9) + (R)-2-Acetylamino-3-naphthalen-2-yl-propionic acid ethyl ester (136015-51-5)

Guidance literature:

With potassium chloride; In dimethyl sulfoxide; at 39 ℃; for 10h; subtilisin Carlsberg, pH 6.9;

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

Reference yield: 48.0%

2-Acetylamino-3-naphthalen-2-yl-propionic acid ethyl ester (172214-89-0) → (S)-N-acetyl-3-(2-naphthyl)alanine (37439-99-9)

Guidance literature:

With sodium hydroxide; potassium chloride; sodium hydrogencarbonate; In acetonitrile; for 5h; Ambient temperature; subtilisin, pH 7.8;

DOI:10.1016/S0957-4166(00)80371-7

upstream raw materials:

ethyl 2-(hydroxyimino)-3-(naphthalen-3-yl)propanoate

2-amino-3-(2-naphthyl)propanoic acid

acetic anhydride

acetylamino-[2]naphthylmethyl-malonic acid diethyl ester

Downstream raw materials:

methyl (S)-2-amino-3-(naphthalen-2-yl)propanoate hydrochloride

L-3-(2-naphthyl)alanine

(R)-2-naphthylalanine

(R)-2-acetamido-3-(naphthalen-2-yl)propanoic acid

Refernces

• 1、 Wende, Raffael C.,Seitz, Alexander,Niedek, Dominik,Schuler, S?ren M. M.,Hofmann, Christine,Becker, Jonathan,Schreiner, Peter R.. "The Enantioselective Dakin-West Reaction". . p. 2719 - 2723. Retrieved 2016/02/27.
• 2、 Zhang, Xiaowei,Huang, Kexuan,Hou, Guohua,Cao, Bonan,Zhang, Xumu. "Electron-donating and rigid p-stereogenic bisphospholane ligands for highly enantioselective rhodium-catalyzed asymmetric hydrogenations". supporting information; experimental part. p. 6421 - 6424. Retrieved 2010/12/19.