(1S,2S)-2-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-N,N-bis(2H5)ethyl-1-phenylcyclopropane-1-carboxamide

• ChemBase ID: 167615
• Molecular Formular: C23H24N2O3
• Molecular Mass: 376.44826
• Monoisotopic Mass: 376.17869264
• SMILES: c1ccc2c(c1)C(=O)N(C2=O)C[C@H]1C[C@@]1(C(=O)N(CC)CC)c1ccccc1
• Canonical SMILES: CCN(C(=O)[C@]1(C[C@@H]1CN1C(=O)c2c(C1=O)cccc2)c1ccccc1)CC
• InChI: InChI=1S/C23H24N2O3/c1-3-24(4-2)22(28)23(16-10-6-5-7-11-16)14-17(23)15-25-20(26)18-12-8-9-13-19(18)21(25)27/h5-13,17H,3-4,14-15H2,1-2H3/t17-,23-/m1/s1
• InChIKey: JOTWZGIFEGRKFM-UZUQRXQVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S)-2-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-N,N-bis(^2H₅)ethyl-1-phenylcyclopropane-1-carboxamide
• IUPAC Traditional name: (1S,2S)-2-[(1,3-dioxoisoindol-2-yl)methyl]-N,N-bis(^2H₅)ethyl-1-phenylcyclopropane-1-carboxamide
• Synonyms: cis-2-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-N,N-diethyl-1-phenylcyclopropanecarboxamide-d10; (1R,2S)-2-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-N,N-diethyl-1-phenylcyclopropanecarboxamide-d10

Database IDs

• PubChem SID: 162261748
• PubChem CID: 71316170

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.9642646
• LogD (pH = 7.4): 2.9642646
• Log P: 2.9642646
• Molar Refractivity: 108.1022 cm^3
• Polarizability: 40.77227 Å^3
• Polar Surface Area: 57.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - D449102

Labelled Milnacipran intermediate.

REFERENCES

• Bonnaud, B., et al.: J. Med. Chem., 30, 318 (1987)