N-{2-[(1S)-6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide

• ChemBase ID: 167591
• Molecular Formular: C16H23NO3
• Molecular Mass: 277.35872
• Monoisotopic Mass: 277.1677936
• SMILES: c1c(c(c2c(c1)CC[C@H]2CCNC(=O)CC)CCO)O
• Canonical SMILES: OCCc1c(O)ccc2c1[C@H](CCNC(=O)CC)CC2
• InChI: InChI=1S/C16H23NO3/c1-2-15(20)17-9-7-12-4-3-11-5-6-14(19)13(8-10-18)16(11)12/h5-6,12,18-19H,2-4,7-10H2,1H3,(H,17,20)/t12-/m0/s1
• InChIKey: NHNKXHOSEOOXLP-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{2-[(1S)-6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide
• IUPAC Traditional name: N-{2-[(1S)-6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl]ethyl}propanamide
• Synonyms: N-[2-[(1S)-2,3-Dihydro-6-hydroxy-7-(2-hydroxyethyl)-1H-inden-1-yl]ethyl]propanamid; (S)-N-[2-(6-Hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-iden-1-yl)ethyl]propionamide; (S)-N-[2-[2,3-Dihydro-6-hydroxy-7-(2-hydroxyethyl)-1H-inden-1-yl]ethyl]propanamide

Database IDs

• CAS Number: 196597-88-3
• PubChem SID: 162261724
• PubChem CID: 10956802

CALCULATED PROPERTIES

• Acid pKa: 9.928072
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.9060706
• LogD (pH = 7.4): 1.9048088
• Log P: 1.9060873
• Molar Refractivity: 79.2975 cm^3
• Polarizability: 30.290066 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Pale-Brown Solid

DETAILS

Toronto Research Chemicals - D449020

Intermediate in the production of Ramelteon.

REFERENCES

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