3-(2-chloroacetyl)-2-[(2-chloroethyl)amino](4,4,5,5-2H4)-1,3,2λ5-oxazaphosphinan-2-one

• ChemBase ID: 176017
• Molecular Formular: C7H13Cl2N2O3P
• Molecular Mass: 275.069481
• Monoisotopic Mass: 274.00408428
• SMILES: O1CCCN(P1(=O)NCCCl)C(=O)CCl
• Canonical SMILES: ClCCNP1(=O)OCCCN1C(=O)CCl
• InChI: InChI=1S/C7H13Cl2N2O3P/c8-2-3-10-15(13)11(7(12)6-9)4-1-5-14-15/h1-6H2,(H,10,13)
• InChIKey: KJRISYCCYWZCOF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-chloroacetyl)-2-[(2-chloroethyl)amino](4,4,5,5-^2H₄)-1,3,2λ^5-oxazaphosphinan-2-one
• IUPAC Traditional name: 3-(2-chloroacetyl)-2-[(2-chloroethyl)amino](4,4,5,5-^2H₄)-1,3,2λ^5-oxazaphosphinan-2-one
• Synonyms: 2-Chloro-1-[2-[(2-chloroethyl)amino]dihydro-2-oxido-2H-1,3,2-oxazaphosphorin-3(4H)-yl]ethanone-d4; 3-(Chloroacetyl)-N-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine-d4 2-Oxide; 2'-Oxo Ifosfamide-d4

Database IDs

• PubChem SID: 164231927
• PubChem CID: 71751377

CALCULATED PROPERTIES

• Acid pKa: 11.905385
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.26566625
• LogD (pH = 7.4): -0.26567814
• Log P: -0.2656661
• Molar Refractivity: 58.5572 cm^3
• Polarizability: 23.549757 Å^3
• Polar Surface Area: 58.64 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Brown Oil

DETAILS

Toronto Research Chemicals - O856952

Labelled Ifosfamide intermediate

REFERENCES

• O'Byrne, K., et al.: Oncol., 56, 13 (1999)
• Misiura, K., et al.: Anti-Cancer Drugs, 12, 453 (1999)