benzyl N-[(2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]carbamate

• ChemBase ID: 175771
• Molecular Formular: C24H33N3O6
• Molecular Mass: 459.53532
• Monoisotopic Mass: 459.23693579
• SMILES: [C@]12(N([C@H](C(=O)N3C1CCC3)CC(C)C)C(=O)[C@@](O2)(NC(=O)OCc1ccccc1)C(C)C)O
• Canonical SMILES: CC(C[C@H]1C(=O)N2CCCC2[C@]2(N1C(=O)[C@@](O2)(NC(=O)OCc1ccccc1)C(C)C)O)C
• InChI: InChI=1S/C24H33N3O6/c1-15(2)13-18-20(28)26-12-8-11-19(26)24(31)27(18)21(29)23(33-24,16(3)4)25-22(30)32-14-17-9-6-5-7-10-17/h5-7,9-10,15-16,18-19,31H,8,11-14H2,1-4H3,(H,25,30)/t18-,19?,23+,24-/m0/s1
• InChIKey: ZVXZDRXFYFSCMA-DLZXLQJJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecan-4-yl]carbamate
• IUPAC Traditional name: benzyl N-[(2S,4R,7S)-2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecan-4-yl]carbamate
• Synonyms: (2R,5S,10aS,10bS)-Octahydro-10b-hydroxy-5-isobutyl-2-isopropyl-3,6-dioxo-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazine-2-carbamic Acid Benzyl Ester; [2R-(2α,5α,10aβ,10bα)]-[Octahydro-10b-hydroxy-2-(1-methylethyl)-5-(2-methylpropyl)-3,6-dioxo-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-carbamic Acid

Database IDs

• CAS Number: 24177-09-1
• PubChem SID: 164231681
• PubChem CID: 71751277

CALCULATED PROPERTIES

• Acid pKa: 9.69512
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.610961
• LogD (pH = 7.4): 3.6087954
• Log P: 3.6109886
• Molar Refractivity: 119.3656 cm^3
• Polarizability: 46.99107 Å^3
• Polar Surface Area: 108.41 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - O236480

Used in the synthesis of Ergot alkaloids.