(1S,2S)-2-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1-phenylcyclopropane-1-carboxylic acid

• ChemBase ID: 176621
• Molecular Formular: C19H15NO4
• Molecular Mass: 321.3267
• Monoisotopic Mass: 321.10010797
• SMILES: c1ccc2c(c1)C(=O)N(C2=O)C[C@H]1C[C@]1(c1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)[C@]1(C[C@@H]1CN1C(=O)c2c(C1=O)cccc2)c1ccccc1
• InChI: InChI=1S/C19H15NO4/c21-16-14-8-4-5-9-15(14)17(22)20(16)11-13-10-19(13,18(23)24)12-6-2-1-3-7-12/h1-9,13H,10-11H2,(H,23,24)/t13-,19-/m1/s1
• InChIKey: XWJCCJTWOLBUSW-BFUOFWGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S)-2-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1-phenylcyclopropane-1-carboxylic acid
• IUPAC Traditional name: (1S,2S)-2-[(1,3-dioxoisoindol-2-yl)methyl]-1-phenylcyclopropane-1-carboxylic acid
• Synonyms: cis-2-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-1-phenyl-cyclopropanecarboxylic Acid; (1R,2S)-rel-2-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-1-phenyl-cyclopropanecarboxylic Acid; cis-1-Phenyl-2-(phthalimidomethyl)cyclopropanecarboxylic Acid

Database IDs

• CAS Number: 69160-56-1
• PubChem SID: 164232531
• PubChem CID: 12456580

CALCULATED PROPERTIES

• Acid pKa: 3.7315607
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.8419252
• LogD (pH = 7.4): -0.6822422
• Log P: 2.6102393
• Molar Refractivity: 86.9894 cm^3
• Polarizability: 32.734444 Å^3
• Polar Surface Area: 74.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - P336000

Milnacipran intermediate.

REFERENCES

• Bonnaud, B., et al.: J. Med. Chem., 30, 318 (1987)
• Chen, C., et al.: Bioorg. Med. Chem. Lett., 18, 1346 (1987)