N-{2-[(1S)-6-(benzyloxy)-5-bromo-7-(prop-2-en-1-yl)-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide

• ChemBase ID: 159677
• Molecular Formular: C24H28BrNO2
• Molecular Mass: 442.38862
• Monoisotopic Mass: 441.13034114
• SMILES: c1(c(c(c2c(c1)CC[C@H]2CCNC(=O)CC)CC=C)OCc1ccccc1)Br
• Canonical SMILES: C=CCc1c2[C@H](CCNC(=O)CC)CCc2cc(c1OCc1ccccc1)Br
• InChI: InChI=1S/C24H28BrNO2/c1-3-8-20-23-18(13-14-26-22(27)4-2)11-12-19(23)15-21(25)24(20)28-16-17-9-6-5-7-10-17/h3,5-7,9-10,15,18H,1,4,8,11-14,16H2,2H3,(H,26,27)/t18-/m0/s1
• InChIKey: DVFZQAWYEJXGJV-SFHVURJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{2-[(1S)-6-(benzyloxy)-5-bromo-7-(prop-2-en-1-yl)-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide
• IUPAC Traditional name: N-{2-[(1S)-6-(benzyloxy)-5-bromo-7-(prop-2-en-1-yl)-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide
• Synonyms: N-[2-[(1S)-5-Bromo-2,3-dihydro-6-hydroxy-7-(2-propen-1-yl)-1H-inden-1-yl]ethyl]propanamide; (S)-N-[2-[5-Bromo-2,3-dihydro-6-hydroxy-7-(2-propenyl)-1H-inden-1-yl]ethyl]propanamide; (S)-N-[2-[7-Allyl-5-bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl]ethyl]propanamide

Database IDs

• CAS Number: 196597-86-1
• PubChem SID: 162253812
• PubChem CID: 71313090

CALCULATED PROPERTIES

• Acid pKa: 14.955441
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.1224656
• LogD (pH = 7.4): 6.1224666
• Log P: 6.1224666
• Molar Refractivity: 118.7316 cm^3
• Polarizability: 45.52097 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - A549665

Intermediate in the production of Ramelteon.

REFERENCES

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