(1R,9S,10R)-10-(hydroxymethyl)-4-methyl-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-5-one

• ChemBase ID: 160695
• Molecular Formular: C10H12N2O4
• Molecular Mass: 224.21328
• Monoisotopic Mass: 224.07970687
• SMILES: [C@H]12C[C@@H](O[C@@H]1CO)n1c(nc(=O)c(c1)C)O2
• Canonical SMILES: OC[C@H]1O[C@@H]2C[C@@H]1Oc1n2cc(c(=O)n1)C
• InChI: InChI=1S/C10H12N2O4/c1-5-3-12-8-2-6(7(4-13)15-8)16-10(12)11-9(5)14/h3,6-8,13H,2,4H2,1H3/t6-,7+,8+/m0/s1
• InChIKey: JCSNHEYOIASGKU-XLPZGREQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,10R)-10-(hydroxymethyl)-4-methyl-8,11-dioxa-2,6-diazatricyclo[7.2.1.0^2,^7]dodeca-3,6-dien-5-one
• IUPAC Traditional name: (1R,9S,10R)-10-(hydroxymethyl)-4-methyl-8,11-dioxa-2,6-diazatricyclo[7.2.1.0^2,^7]dodeca-3,6-dien-5-one
• Synonyms: (2R,3R,5R)-2,3-Dihydro-3-(hydroxymethyl)-8-methyl-2,5-methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one; 2,3'-Anhydro-1-(2'-deoxy-β-D-threo-pentofuranosyl)thymine; 2,3'-O-Cyclothymidine; NSC 144601; O2,3'-Cyclothymidine; 2,3'-Anhydrothymidine

Database IDs

• CAS Number: 15981-92-7
• PubChem SID: 162254830
• PubChem CID: 6915752

CALCULATED PROPERTIES

• Acid pKa: 14.588505
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.029251672
• LogD (pH = 7.4): 0.029251644
• Log P: 0.029251672
• Molar Refractivity: 52.6216 cm^3
• Polarizability: 20.801762 Å^3
• Polar Surface Area: 71.36 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 228-232°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A656500

An intermediate in the preparation of thymidine derivatives

REFERENCES

• el Kouni, M., et al.: Biochem. Pharmacol., 51, 1687 (1996)