N-{4-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]butyl}-2,2,2-trifluoroacetamide

• ChemBase ID: 179063
• Molecular Formular: C9H11F3N2O4
• Molecular Mass: 268.1898496
• Monoisotopic Mass: 268.0670915
• SMILES: O1C(=O)[C@@H](NC1=O)CCCCNC(=O)C(F)(F)F
• Canonical SMILES: O=C1N[C@H](C(=O)O1)CCCCNC(=O)C(F)(F)F
• InChI: InChI=1S/C9H11F3N2O4/c10-9(11,12)7(16)13-4-2-1-3-5-6(15)18-8(17)14-5/h5H,1-4H2,(H,13,16)(H,14,17)/t5-/m0/s1
• InChIKey: KWNIHCJDDYRQFW-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]butyl}-2,2,2-trifluoroacetamide
• IUPAC Traditional name: N-{4-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]butyl}-2,2,2-trifluoroacetamide
• Synonyms: N-[4-[(4S)-2,5-Dioxo-4-oxazolidinyl]butyl]-2,2,2-trifluoroacetamide; (S)-N-[4-(2,5-Dioxo-4-oxazolidinyl)butyl]-2,2,2-trifluoroacetamide; Lys(Tfa)-NCA; N6-Trifluoroacetyl-L-lysine N-Carboxyanhydride

Database IDs

• CAS Number: 42267-27-6
• PubChem SID: 164234973
• PubChem CID: 6451853

CALCULATED PROPERTIES

• Acid pKa: 6.226916
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.60151935
• LogD (pH = 7.4): -0.10445523
• Log P: 0.66697896
• Molar Refractivity: 51.3564 cm^3
• Polarizability: 19.643194 Å^3
• Polar Surface Area: 84.5 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T788530

Used in the synthesis of new arborescent architectures of poly(L-lysine), called lysine dendrigraft (DGL) polymers. DGL polymers were prepd. through a multiple-generation scheme (up to generation 5) in a weakly acidic aq. medium by polycondensing N.vepsiln.-trifluoroacetyl-L-lysine-N-carboxyanhydride (Lys(Tfa)-NCA) onto the previous generation G(n-1) of DGL, which was used as a macroinitiator.

REFERENCES

• Svenson, S., et al.: Adv. Drug Delivery Rev., 57, 2106 (2005)
• Shen, X., et al.: Org. Biomol. Chem., 5, 3674 (2005)