benzyl N-[(5E)-4-hydroxy-7-oxooct-5-en-1-yl]carbamate

• ChemBase ID: 171013
• Molecular Formular: C16H21NO4
• Molecular Mass: 291.34224
• Monoisotopic Mass: 291.14705816
• SMILES: CC(=O)/C=C/C(CCCNC(=O)OCc1ccccc1)O
• Canonical SMILES: OC(/C=C/C(=O)C)CCCNC(=O)OCc1ccccc1
• InChI: InChI=1S/C16H21NO4/c1-13(18)9-10-15(19)8-5-11-17-16(20)21-12-14-6-3-2-4-7-14/h2-4,6-7,9-10,15,19H,5,8,11-12H2,1H3,(H,17,20)/b10-9+
• InChIKey: STMLPBMOYVXYLB-MDZDMXLPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(5E)-4-hydroxy-7-oxooct-5-en-1-yl]carbamate
• IUPAC Traditional name: benzyl N-[(5E)-4-hydroxy-7-oxooct-5-en-1-yl]carbamate
• Synonyms: N-[(5E)-4-Hydroxy-7-oxo-5-octen-1-yl]-carbamic Acid Phenylmethyl Ester; N-[(5E)-4-Hydroxy-7-oxo-5-octen-1-yl]carbamic Acid Benzyl Ester

Database IDs

• CAS Number: 866488-35-9
• PubChem SID: 164226923
• PubChem CID: 11737866

CALCULATED PROPERTIES

• Acid pKa: 14.789777
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.9711531
• LogD (pH = 7.4): 1.9711531
• Log P: 1.9711531
• Molar Refractivity: 81.1007 cm^3
• Polarizability: 31.099194 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone

DETAILS

Toronto Research Chemicals - H948835

Intermediate in the preparation of Halofuginone.

REFERENCES

• Takeuchi, Y., et al.: Chem. Pharm. Bull., 53, 868 (2005)