benzyl N-[(3R)-2,6-dioxooxan-3-yl]carbamate

• ChemBase ID: 178341
• Molecular Formular: C13H13NO5
• Molecular Mass: 263.24602
• Monoisotopic Mass: 263.07937252
• SMILES: C1(=O)CC[C@H](C(=O)O1)NC(=O)OCc1ccccc1
• Canonical SMILES: O=C(N[C@@H]1CCC(=O)OC1=O)OCc1ccccc1
• InChI: InChI=1S/C13H13NO5/c15-11-7-6-10(12(16)19-11)14-13(17)18-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,14,17)/t10-/m1/s1
• InChIKey: YIXAMRRMFCPXNC-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(3R)-2,6-dioxooxan-3-yl]carbamate
• IUPAC Traditional name: benzyl N-[(3R)-2,6-dioxooxan-3-yl]carbamate
• Synonyms: (R)-(Tetrahydro-2,6-dioxo-2H-pyran-3-yl)-carbamic Acid Phenylmethyl Ester; [(3R)-Tetrahydro-2,6-dioxo-2H-pyran-3-yl]-carbamic Acid Phenylmethyl

Database IDs

• CAS Number: 71869-80-2
• PubChem SID: 164234251
• PubChem CID: 12793798

CALCULATED PROPERTIES

• Acid pKa: 13.01395
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3649209
• LogD (pH = 7.4): 1.3649199
• Log P: 1.3649209
• Molar Refractivity: 63.7623 cm^3
• Polarizability: 25.31752 Å^3
• Polar Surface Area: 81.7 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Glacial Acetone
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - T293460

Used in the synthesis of Cbz-aminoglutarimides and Cbz-succinimides, for their anticonvulsant activity.

REFERENCES

• Park, M. et al.: Bioorgan. Med. Chem. Lett. 6, 1297 (1996)
• Lee, J. et al.: Arch. Pharm. Res. 19, 248 (1996)