Phthaloyl-L-alanine

Base Information

• Chemical Name: Phthaloyl-L-alanine
• CAS No.: 4192-28-3
• Molecular Formula: C11H9 N O4
• Molecular Weight: 219.197
• DSSTox Substance ID: DTXSID80352170
• Nikkaji Number: J231.823G
• Wikidata: Q72472828
• ChEMBL ID: CHEMBL2429921
• Mol file: 4192-28-3.mol

Synonyms:4192-28-3;Phthaloyl-L-alanine;PHT-ALA-OH;(S)-2-(1,3-Dioxoisoindolin-2-yl)propanoic acid;(2S)-2-(1,3-dioxoisoindol-2-yl)propanoic acid;N-phthaloyl-l-alanine;MFCD00190990;(s)-N-phthaloylalanine;Pht-Ala-OH, AldrichCPR;SCHEMBL125972;CHEMBL2429921;(S)-2-phthalimidopropionic acid;DTXSID80352170;OZWUITKBAWTEAQ-LURJTMIESA-N;AKOS015910116;FD21024;AC-29809;AS-19227;AM20040442;CS-0094070;EN300-235768;(S)-2-(1,3-Dioxoisoindolin-2-yl)propanoicacid;dl-2-(1,3-dioxoisoindolin-2-yl)propanoic acid;(2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanoic acid

Chemical Property of Phthaloyl-L-alanine

Chemical Property:

• Melting Point: 139 - 141oC
• Boiling Point: 407.9±28.0 °C(Predicted)
• PKA: 3?+-.0.10(Predicted)
• PSA: 74.68000
• Density: 1.467±0.06 g/cm3(Predicted)
• LogP: 0.69360
• Storage Temp.: Store at 0°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 219.05315777
• Heavy Atom Count: 16
• Complexity: 328

Purity/Quality:

99% ^*data from raw suppliers

Phthaloyl-L-alanine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)O)N1C(=O)C2=CC=CC=C2C1=O
• Isomeric SMILES: C[C@@H](C(=O)O)N1C(=O)C2=CC=CC=C2C1=O

Technology Process of Phthaloyl-L-alanine

There total 14 articles about Phthaloyl-L-alanine 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: 99.0%

phthalic anhydride (85-44-9) + L-alanin (56-41-7,25191-17-7,18875-37-1) → Phth-L-Ala-OH (4192-28-3)

Guidance literature:

In water; for 0.5h; microwave irradiation;

DOI:10.1021/ol048771l

Reference yield: 95.0%

(S)-benzyl 2-(1,3-dioxoisoindolin-2-yl)propanoate (42406-36-0) → Phth-L-Ala-OH (4192-28-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/0040-4039(96)00977-X

Reference yield: 87.0%

L-alanin (56-41-7,25191-17-7,18875-37-1) + N-ethoxycarbonylphthalimide (22509-74-6) → Phth-L-Ala-OH (4192-28-3)

Guidance literature:

With sodium carbonate; In water; at 20 ℃; for 3h;

DOI:10.1002/anie.201306625

upstream raw materials:

phthalic anhydride

L-alanin

D-Alanine

l-alanine

Downstream raw materials:

ethyl 2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]-3-methyl-5-oxo-2,5-dihydroisoxazole-4-carboxylate

ethyl 2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]-4-methyl-5-oxo-2,5-dihydroisoxazole-3-carboxylate

(S)-2-(1,3-dioxoisoindolin-2-yl)-N-phenylpropanamide

ethyl 2-(1,3-dioxoisoindolin-2-yl)propanoate

Refernces

• 1、 Sharma, Renu,Nagar, Meena. "Synthesis, structural, and antibacterial studies of some mixed ligand complexes of Zn(II), Cd(II), and Hg(II) derived from citral thiosemicarbazone and N-phthaloyl amino acids". . p. 2863 - 2875. Retrieved 2006.
• 2、 Tukhtaev,Yusupov,Vinogradova. "Synthesis of new amides based on N-Phthaloyl-α-Amino Acids". . p. 3049 - 3058. Retrieved 2021/05/28.
• 3、 Mehrez, Asma,Chakroun, Ibtissem,Mtat, Dalila,Mansour, Hédi Ben,Touati, Ridha. "Synthesis of novel phthalimido oxime pseudoesters and evaluation of their cytotoxicity". . p. 1 - 8. Retrieved 2020/11/02.