N-Benzyloxycarbonyl-L-3-phenylalanin

Benzyloxycarbonyl-L-phenylalanine

HCID 70878CAS 1161-13-3

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Grundinformationen

Standard-SMILES: O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1
InChIKey: RRONHWAVOYADJL-HNNXBMFYSA-N
Summenformel: C17H17NO4
Durchschnittliche Molmasse: 299,32 g/mol
Monoisotopische Masse: 299,11575802

Überblick

RN given refers to (L-Phe)-isomer

Namen und Bezeichner

Bevorzugter Name: Benzyloxycarbonyl-L-phenylalanine
IUPAC: (2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid
Lokaler Name: N-Benzyloxycarbonyl-L-3-phenylalanin
Englischer Name: N-Cbz-L-Phenylalanine
Summenformel: C17H17NO4
Molmasse: 299.32

Namen und Synonyme

1161-13-3CarbobenzoxyphenylalanineZ-Phebenzyloxycarbonyl-L-phenylalaninebenzyloxycarbonylphenylalanineDTXSID30151276RefChem:829269DTXCID3073767214-599-3Z-Phe-OHN-CBZ-L-PHENYLALANINEZ-L-Phenylalanine

Weitere Namen anzeigen

Cbz-PheZ-L-PHE-OHCBZ-L-PHECBZ-L-Phe-OHL-PHENYLALANINE, N-[(PHENYLMETHOXY)CARBONYL]-Z-L

N-Carbobenzoxy-L-phenylalanineN-(Carbobenzyloxy)-L-phenylalanineCbz-Phe-OHCBZ-L-PhenylalanineCarbobenzoxy-L-phenylalanineMFCD00020418(Benzyloxycarbonyl)phenylalanine((benzyloxy)carbonyl)-L-phenylalanine

Datenbank-Bezeichner

CAS: 1161-13-3
PubChem CID: 70878
DTXSID: DTXSID30151276
ChEMBL: CHEMBL66143
EC Number: 214-599-3
Nikkaji: J80.209C

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,1
Polarare Oberfläche (TPSA): 75,6 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 4
Frei drehbare Bindungen: 7
Schwere Atome: 22
Formalladung: 0
Komplexität: 360

Physikochemische Eigenschaften

Schmelzpunkt: 85 · 85-87 °C(lit.)
Siedepunkt: 440.65 °C · 440.65°C (rough estimate)
Dichte: 1.1441 · 1.1441 (rough estimate)
Brechungsindex: 5.3 ° · 5.3 ° (C=4, AcOH)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit: DMF (Sparingly), DMSO (Slightly), Methanol (Slightly)
pka: 3.86 · 3.86±0.10(Predicted)
Aggregatzustand: Powder
Farbe: White to off-white
BRN: 2222826 · 2222826
Major Application: peptide synthesis
InChI: 1S/C17H17NO4/c19-16(20)15(11-13-7-3-1-4-8-13)18-17(21)22-12-14-9-5-2-6-10-14/h1-10,15H,11-12H2,(H,18,21)(H,19,20)/t15-/m0/s1
InChIKey: RRONHWAVOYADJL-HNNXBMFYSA-N
SMILES: OC(=O)[C@H](Cc1ccccc1)NC(=O)OCc2ccccc2
CAS Datenbank: 1161 · 1161-13-3(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Danger

H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P233, P260, P261, P264, P264+P265, P271, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (33.3%)

Sicherheitsdaten

wgk: 3
hs_code: 29242990
RTECS-Nr.: AY4343000
risk_code: 62-36/37/38-20/21/22
hazard_code: Xn
safety_code: 22-24/25-36-26
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Anwendungen · 1 Eintrag

VerwendenN-Cbz-L-Phenylalanine is used in the synthesis of neurokinin antagonists. Furthermore it is used in the preparation of Co(II), Zn(II), and Cd(II) complexes with N-benzyloxycarbonyl-S-phen ylalanine that displays antimicrobial activity against common strains of bacteria.