(S)-(+)-N-(3,5-Dinitrobenzoyl)-alpha-phenylglycine

Base Information

• Chemical Name: (S)-(+)-N-(3,5-Dinitrobenzoyl)-alpha-phenylglycine
• CAS No.: 90761-62-9
• Molecular Formula: C15H11N3O7
• Molecular Weight: 345.268
• DSSTox Substance ID: DTXSID50426493
• Nikkaji Number: J636.920K
• Wikidata: Q72472476
• Mol file: 90761-62-9.mol

Synonyms:90761-62-9;(S)-2-(3,5-dinitrobenzamido)-2-phenylacetic acid;(S)-(+)-N-(3,5-Dinitrobenzoyl)-alpha-phenylglycine;(2S)-2-[(3,5-dinitrobenzoyl)amino]-2-phenylacetic acid;(R)-(-)-N-(3,5-Dinitrobenzoyl)-alpha-phenylglycine;(b)-(+)-N-(3,5-Dinitrobenzoyl)-alpha-phenylglycine;C15H11N3O7;C15-H11-N3-O7;N-3,5-Dinitrobenzoyl-L-phenyl glycine;S-(+)-N-(3,5-Dinitrobenzoyl)phenylglycine;D-3,5-Dinitrobenzoylleucine;SCHEMBL1285898;Benzeneacetic acid, .alpha.-[(3,5-dinitrobenzoyl)amino]-, (.alpha.R)-;(2S)-2-[(3,5-dinitrobenzoyl)amino]-2-phenyl-acetic acid;DTXSID50426493;3,5-dinitrobenzoyl-l-phenylglycine;MFCD00064470;AKOS015888884;AKOS037643339;N-(3,5-Dinitrobenzoyl)-L-phenylglycine;AS-14339;AS-81140;CS-0131563;Benzeneacetic acid,a-[(3,5-dinitrobenzoyl)amino]-,(as)-;(2S)-2-[(3,5-dinitrophenyl)formamido]-2-phenylacetic acid;(S)-(+)-N-(3,5-Dinitrobenzoyl)-alpha-phenylglycine, 99%;Benzeneacetic acid, .alpha.-[(3,5-dinitrobenzoyl)amino]-, (.alpha.S)-;N-(3,5-Dinitrobenzoyl)-L-alpha-phenylglycine, purum, >=98.0% (sum of enantiomers, HPLC)

Chemical Property of (S)-(+)-N-(3,5-Dinitrobenzoyl)-alpha-phenylglycine

Chemical Property:

• Vapor Pressure: 8.34E-14mmHg at 25°C
• Melting Point: 218-220 °C(lit.)
• Refractive Index: 1.662
• Boiling Point: 569.4 °C at 760 mmHg
• PKA: 3.34±0.10(Predicted)
• Flash Point: 298.2 °C
• PSA: 158.04000
• Density: 1.527g/cm³
• LogP: 3.49600
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 345.05969970
• Heavy Atom Count: 25
• Complexity: 514

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-(+)-N-(3,5-Dinitrobenzoyl)-α-phenylglycine 99% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(=O)O)NC(=O)C2=CC(=CC(=C2)[N+](=O)[O-])[N+](=O)[O-]
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H](C(=O)O)NC(=O)C2=CC(=CC(=C2)[N+](=O)[O-])[N+](=O)[O-]

Technology Process of (S)-(+)-N-(3,5-Dinitrobenzoyl)-alpha-phenylglycine

There total 5 articles about (S)-(+)-N-(3,5-Dinitrobenzoyl)-alpha-phenylglycine 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: 92.0%

(S)-2-phenylglycine (2935-35-5) + 3,5-dinitrobenoyl chloride (99-33-2) → (S)-(+)-N-(3,5-dinitrobenzoyl)-α-phenylglycine (90761-62-9)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 168000h;

DOI:10.1039/b617607k

Reference yield:

(R,S)-N-(3,5-dinitrobenzoyl)-phenylglycine methyl ester → (R)-(-)-methyl N-(3,5-dinitrobenzoyl)-α-phenylglycinate (69632-50-4) + (S)-(+)-N-(3,5-dinitrobenzoyl)-α-phenylglycine (90761-62-9) + (R)-(-)-N-(3,5-dinitrobenzoyl)-α-phenylglycine (74927-72-3) + (S)-(+)-methyl N-(3,5-dinitrobenzoyl)-α-phenylglycinate

Guidance literature:

With sodium hydroxide; N-pivaloyl-(3,5-dimethylphenyl)-L-prolinamide; In tetrachloromethane; dichloromethane; water; at 0 ℃; Title compound not separated from byproducts.;

DOI:10.1021/ol026517s

Reference yield:

(R)-(-)-N-(3,5-dinitrobenzoyl)-α-phenylglycine (74958-71-7) → (S)-(+)-N-(3,5-dinitrobenzoyl)-α-phenylglycine (90761-62-9) + (R)-(-)-N-(3,5-dinitrobenzoyl)-α-phenylglycine (74927-72-3)

Guidance literature:

With N-[(R)-1-(1-naphthyl)ethyl]carbamoyl-derivatized cyclofructan-6 column; In ethanol; n-heptane; trifluoroacetic acid; at 20 ℃; Resolution of racemate;

DOI:10.1021/ac902257a

upstream raw materials:

(S)-2-phenylglycine

3,5-dinitrobenoyl chloride

Benzoylformic acid

phenylglycin

Downstream raw materials:

BDNP

DDNP

ammonium N-(3,5-dinitrobenzoyl)-α-phenylglycinate

n-propylammonium N-(3,5-dinitrobenzoyl)-α-phenylglycinate

Refernces

• 1、 Hallett, Andrew J.,Kwant, Gerard J.,De Vries, Johannes G.. "Continuous separation of racemic 3,5-dinitrobenzoyl-amino acids in a centrifugal contact separator with the aid of cinchona-based chiral host compounds". supporting information; experimental part. p. 2111 - 2120. Retrieved 2009/09/30.
• 2、 Cichelli, Julie,Zharov, Ilya. "Chiral permselectivity in nanoporous opal films surface-modified with chiral selector moieties". . p. 1870 - 1875. Retrieved 2008/02/07.