benzyl 2-(2-benzylprop-2-enamido)acetate

• ChemBase ID: 166051
• Molecular Formular: C19H19NO3
• Molecular Mass: 309.35906
• Monoisotopic Mass: 309.13649347
• SMILES: c1(CC(=C)C(=O)NCC(=O)OCc2ccccc2)ccccc1
• Canonical SMILES: O=C(CNC(=O)C(=C)Cc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C19H19NO3/c1-15(12-16-8-4-2-5-9-16)19(22)20-13-18(21)23-14-17-10-6-3-7-11-17/h2-11H,1,12-14H2,(H,20,22)
• InChIKey: YKINYFHTXSOMQZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 2-(2-benzylprop-2-enamido)acetate
• IUPAC Traditional name: benzyl 2-(2-benzylprop-2-enamido)acetate
• Synonyms: N-[1-Oxo-2-(phenylmethyl)-2-propen-1-yl]glycine Phenylmethyl Ester; N-[1-Oxo-2-(phenylmethyl)-2-propenyl]glycine Phenylmethyl Ester; Racecadotril Impurity F; Benzyl[(2-benzylprop-2-enoyl)amino]acetate; 2-Des(acetylthiomethyl)-2-methylene Racecadotril

Database IDs

• CAS Number: 87428-99-7
• PubChem SID: 162260184
• PubChem CID: 13242778

CALCULATED PROPERTIES

• Acid pKa: 13.364066
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.2719352
• LogD (pH = 7.4): 3.2719536
• Log P: 3.2719543
• Molar Refractivity: 88.5297 cm^3
• Polarizability: 34.541363 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288425

An impurity of the antidiarrheal Racecadotril (R070600).

REFERENCES

• Reddy, K.M. et al.: Pharmazie, 61, 994 (2006)