5-(benzyloxy)-6-methoxy-1H-indole

• ChemBase ID: 130578
• Molecular Formular: C16H15NO2
• Molecular Mass: 253.2958
• Monoisotopic Mass: 253.11027873
• SMILES: COc1cc2c(cc[nH]2)cc1OCc1ccccc1
• Canonical SMILES: COc1cc2[nH]ccc2cc1OCc1ccccc1
• InChI: InChI=1S/C16H15NO2/c1-18-15-10-14-13(7-8-17-14)9-16(15)19-11-12-5-3-2-4-6-12/h2-10,17H,11H2,1H3
• InChIKey: XDLZHWUPJHWVFK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(benzyloxy)-6-methoxy-1H-indole
• IUPAC Traditional name: 5-(benzyloxy)-6-methoxy-1H-indole
• Synonyms: NSC 92529; 5-Benzyloxy-6-methoxyindole; 6-Methoxy-5-(phenylmethoxy)-1H-indole; 5-Benzyloxy-6-methoxy-1H-indole; 5-Benzyloxy-6-methoxyindole; 5-苄氧基-6-甲氧基吲哚

Database IDs

• CAS Number: 4790-04-9
• MDL Number: MFCD00037973
• PubChem SID: 24891584; 162224856
• PubChem CID: 260800

CALCULATED PROPERTIES

• Acid pKa: 16.71476
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.4811385
• LogD (pH = 7.4): 3.4811385
• Log P: 3.4811385
• Molar Refractivity: 74.6835 cm^3
• Polarizability: 30.205097 Å^3
• Polar Surface Area: 34.25 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Benzene; Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White to Pale Brown Solid
• Melting Point: 93-94°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

Sigma Aldrich - B1376

包装
1 g in poly bottle
250 mg in poly bottle
Application
Reactant for preparation of:
• CB2 Cannabinoid receptor ligands1
• Potent antimitotic agents2
• Potent c-ABL inhibitors3
• Eumelanin pigment precursors

REFERENCES

• McBride, C., et al.: Bioorg. Med. Chem. Lett., 16, 3789 (2006)
• Frost, J., et al.: J. Med. Chem., 51, 1904 (2006)