tert-butyl 5-{[(tert-butoxy)carbonyl]oxy}-3-(2-acetamidoethyl)-1H-indole-1-carboxylate

• ChemBase ID: 159178
• Molecular Formular: C22H30N2O6
• Molecular Mass: 418.4834
• Monoisotopic Mass: 418.21038669
• SMILES: c1(ccc2c(c1)c(cn2C(=O)OC(C)(C)C)CCNC(=O)C)OC(=O)OC(C)(C)C
• Canonical SMILES: CC(=O)NCCc1cn(c2c1cc(cc2)OC(=O)OC(C)(C)C)C(=O)OC(C)(C)C
• InChI: InChI=1S/C22H30N2O6/c1-14(25)23-11-10-15-13-24(19(26)29-21(2,3)4)18-9-8-16(12-17(15)18)28-20(27)30-22(5,6)7/h8-9,12-13H,10-11H2,1-7H3,(H,23,25)
• InChIKey: YVQMPLGGLYQKHM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 5-{[(tert-butoxy)carbonyl]oxy}-3-(2-acetamidoethyl)-1H-indole-1-carboxylate
• IUPAC Traditional name: tert-butyl 5-[(tert-butoxycarbonyl)oxy]-3-(2-acetamidoethyl)indole-1-carboxylate
• Synonyms: N,O-Bis(tert-butoxycarbonyl)-normelatonin; N,O-Bis(tert-butoxycarbonyl)-O-demethylmelatonin; N-[2-(N,O-Bis(tert-butoxycarbonyl)-5-hydroxyindol-3-yl)ethyl]acetamide; N,O-Bis(tert-butoxycarbonyl)-5-hydroxymelatonin; [1-(N,O-Bis(tert-butoxycarbonyl))-3-(2-acetamidoethyl)-5-hydroxy]indole; N-Acetyl-N,O-bis(tert-butoxycarbonyl) Serotonin

Database IDs

• PubChem SID: 162253313
• PubChem CID: 71312842

CALCULATED PROPERTIES

• Acid pKa: 15.294658
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.5788555
• LogD (pH = 7.4): 3.5788558
• Log P: 3.5788558
• Molar Refractivity: 111.0778 cm^3
• Polarizability: 44.71115 Å^3
• Polar Surface Area: 95.86 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Pale Brown Foam

DETAILS

Toronto Research Chemicals - A171135

Protected Serotonin.