(R)-N-Acetyl-2-naphthylalanine

Base Information

• Chemical Name: (R)-N-Acetyl-2-naphthylalanine
• CAS No.: 37440-01-0
• Molecular Formula: C15H15NO3
• Molecular Weight: 257.289
• Hs Code.: 29223900
• European Community (EC) Number: 609-430-9
• UNII: 7RZ2WM47TL
• DSSTox Substance ID: DTXSID40958536
• Nikkaji Number: J980.666K
• Mol file: 37440-01-0.mol

Synonyms:37440-01-0;Ac-D-2-Nal-OH;(R)-N-ACETYL-2-NAPHTHYLALANINE;(R)-2-ACETAMIDO-3-(NAPHTHALEN-2-YL)PROPANOIC ACID;N-Acetyl-3-(2-naphthyl)-D-alanine;(2R)-2-acetamido-3-naphthalen-2-ylpropanoic acid;7RZ2WM47TL;(2R)-2-acetamido-3-(naphthalen-2-yl)propanoic acid;(R)-2-Acetylamino-3-(2-naphthyl)propanoic acid;Ac-D-Ala(2-Naph)-OH;Acetyl-3-(2-naphthyl)-D-alanine;UNII-7RZ2WM47TL;SCHEMBL607215;DTXSID40958536;MFCD00079678;AKOS016009532;DS-8348;CS-0154026;C74922;EN300-7379325;2-Naphthalenepropanoic acid, a-(acetylamino)-, (aR)-;2-Naphthalenepropanoic acid, alpha-(acetylamino)-, (alphaR)-;2-NAPHTHALENEPROPANOIC ACID, .ALPHA.-(ACETYLAMINO)-, (.ALPHA.R)-

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

Chemical Property:

• Appearance/Colour: off-white to light yellow-beige granular powder
• Vapor Pressure: 1.21E-12mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 543.438 °C at 760 mmHg
• PKA: 3.59±0.30(Predicted)
• Flash Point: 282.461 °C
• PSA: 66.40000
• Density: 1.244 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:

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

Acetyl-3-(2-naphthyl)-D-alanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

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
• Uses: Acetyl-3-(2-naphthyl)-D-alanine was used to study the aromatic binding site of α-chymotrypsin. It was used to design an asymmetric synthesis of a new cylindrically chiral and air-stable ferrocenyldiphosphine and its application to rhodium-catalyzed asymmetric hydrogenation.

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

There total 12 articles about (R)-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:

(RS)-N-acetyl-2-naphthylalanine (37439-99-9,37440-01-0,58438-02-1) → L-3-(2-naphthyl)alanine (6960-34-5,14108-60-2,58438-03-2,76985-09-6,106107-92-0) + (R)-2-naphthylalanine (76985-09-6,106107-92-0) + (R)-2-acetamido-3-(naphthalen-2-yl)propanoic acid (37440-01-0)

Guidance literature:

With cobalt(II) chloride; at 30 ℃; pH=8; optical yield given as %ee; enantioselective reaction; aq. phosphate buffer; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.molcatb.2011.10.003

Reference yield:

(Z)-2-acetamido-3-(naphthalen-2-yl)acrylic acid → (R)-2-acetamido-3-(naphthalen-2-yl)propanoic acid (37440-01-0)

Guidance literature:

With <(1R)-phenylethyl-FERRIPHOS>; hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; In methanol; under 750.06 Torr;

DOI:10.1016/S0040-4039(98)01832-2

Reference yield:

(Z)-2-acetamido-3-(naphthalen-2-yl)acrylic acid → (RS)-N-acetyl-2-naphthylalanine (37439-99-9,37440-01-0,58438-02-1)

Guidance literature:

With hydrogen; [Rh((R,R)-DIPAMP)(COD)]BF₄; In methanol; at 50 ℃; for 10h; under 7757.43 Torr; Product distribution / selectivity;

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:

Ac-D-Nal2-D-Cpa-D-Pal-Gly-Arg-Pro-D-Ala-NH2

Ac-D-Nal₂-D-Cpa-D-Pal-D-Ala-Lys-Pro-D-Ala-NH₂

Refernces

• 1、 Yang, Yihua,Liu, Shouxin,Li, Junzhang,Tian, Xia,Zhen, Xiaoli,Han, Jianrong. "Convenient method for reduction of C-N double bonds in oximes, imines, and hydrazones using sodium Borohydride-Raney ni system". . p. 2540 - 2554. Retrieved 2012/07/27.
• 2、 -. "CHIRAL PHOSPHORUS COMPOUNDS". Page/Page column 37-39. . Retrieved 2008/12/04.