N-{2-[(1S)-5-bromo-6-hydroxy-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide

• ChemBase ID: 162834
• Molecular Formular: C14H18BrNO2
• Molecular Mass: 312.20222
• Monoisotopic Mass: 311.05209082
• SMILES: c1(c(cc2c(c1)CC[C@H]2CCNC(=O)CC)O)Br
• Canonical SMILES: CCC(=O)NCC[C@@H]1CCc2c1cc(O)c(c2)Br
• InChI: InChI=1S/C14H18BrNO2/c1-2-14(18)16-6-5-9-3-4-10-7-12(15)13(17)8-11(9)10/h7-9,17H,2-6H2,1H3,(H,16,18)/t9-/m0/s1
• InChIKey: FCIPPXPPFSLFJC-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{2-[(1S)-5-bromo-6-hydroxy-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide
• IUPAC Traditional name: N-{2-[(1S)-5-bromo-6-hydroxy-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide
• Synonyms: N-[2-[(1S)-5-Bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl]ethyl]propanamide; (S)-N-[2-(5-Bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl)ethyl]propanamide

Database IDs

• CAS Number: 196597-84-9
• PubChem SID: 162256969
• PubChem CID: 11066924

CALCULATED PROPERTIES

• Acid pKa: 8.388974
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.152971
• LogD (pH = 7.4): 3.1114068
• Log P: 3.1535285
• Molar Refractivity: 75.3494 cm^3
• Polarizability: 28.85783 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol; Tetrahydrofuran
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - B683500

Intermediate in the production of Ramelteon.

REFERENCES

• Uchikawa, O., et al.: J. Med. Chem., 45, 4222 (2002)