methyl (2Z)-2-[(2,3-dichlorophenyl)methylidene]-3-oxobutanoate

• ChemBase ID: 173547
• Molecular Formular: C12H10Cl2O3
• Molecular Mass: 273.112
• Monoisotopic Mass: 272.00069954
• SMILES: c1c(c(c(cc1)/C=C(/C(=O)C)\C(=O)OC)Cl)Cl
• Canonical SMILES: COC(=O)/C(=C\c1cccc(c1Cl)Cl)/C(=O)C
• InChI: InChI=1S/C12H10Cl2O3/c1-7(15)9(12(16)17-2)6-8-4-3-5-10(13)11(8)14/h3-6H,1-2H3/b9-6-
• InChIKey: QQXPSPWWWCQBFM-TWGQIWQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2Z)-2-[(2,3-dichlorophenyl)methylidene]-3-oxobutanoate
• IUPAC Traditional name: methyl (2Z)-2-[(2,3-dichlorophenyl)methylidene]-3-oxobutanoate
• Synonyms: 2-[(2,3-Dichlorophenyl)methylene]-3-oxobutanoic Acid Methyl Ester; Methyl 2-(2,3-Dichlorobenzylidine)acetoacetate; Methyl 2-(2,3-Dichlorobenzylidene)acetoacetate

Database IDs

• CAS Number: 74073-22-6
• PubChem SID: 164229457
• PubChem CID: 11780684

CALCULATED PROPERTIES

• Acid pKa: 18.421923
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.6402717
• LogD (pH = 7.4): 3.6402717
• Log P: 3.6402717
• Molar Refractivity: 67.064 cm^3
• Polarizability: 25.889862 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M301250

An intermediate used in the preparation of dihydropyridine calcium antagonists.

REFERENCES

• Arrowsmith, J.E. et al.: J. Med. Chem., 29, 1696 (1986)
• Yiu, S. et al.: Arch. Pharm., 332, 363 (1986)