tert-butyl N-[(3S)-2-oxooxetan-3-yl]carbamate

• ChemBase ID: 125055
• Molecular Formular: C8H13NO4
• Molecular Mass: 187.19312
• Monoisotopic Mass: 187.0844579
• SMILES: O=C(OC(C)(C)C)N[C@@H]1C(=O)OC1
• Canonical SMILES: O=C(OC(C)(C)C)N[C@H]1COC1=O
• InChI: InChI=1S/C8H13NO4/c1-8(2,3)13-7(11)9-5-4-12-6(5)10/h5H,4H2,1-3H3,(H,9,11)/t5-/m0/s1
• InChIKey: HRJDEHQWXAPGBG-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(3S)-2-oxooxetan-3-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(3S)-2-oxooxetan-3-yl]carbamate
• Synonyms: [(3S)-2-oxo-3-oxetanyl]-1,1-dimethylethyl Ester Carbamic Acid; N-Boc L-Serine β-Lactone; (S)-N-(tert-Butoxycarbonyl)-3-amino-2-oxetanone; N-(tert-Butoxycarbonyl)-L-serine β-lactone; Vederas β-lactone (Boc); N-Boc-L-serine β-lactone; N-Boc-L-serine beta-Lactone; Boc-L-Serine-beta-Lactone; (S)-N-(叔丁氧羰基)-3-氨基-2-丙醇酸丙酯; N-(叔丁氧羰基)-L-丝氨酸 β-内酯; Vederas β-内酯 (Boc); N-叔丁氧羰基-L-丝氨酸 β-内酯; S-N-Boc-丝氨酸内酯

Database IDs

• CAS Number: 98541-64-1
• MDL Number: MFCD01318414
• PubChem SID: 162219405
• PubChem CID: 2763194

CALCULATED PROPERTIES

• Acid pKa: 13.022061
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.5309472
• LogD (pH = 7.4): 0.5309463
• Log P: 0.5309472
• Molar Refractivity: 43.4218 cm^3
• Polarizability: 17.529295 Å^3
• Polar Surface Area: 64.63 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 319°C at 760 mmHg
• Flash Point: 146.7°C
• Density: 1.18g/cm^3
• Vapor Pressure: 0.000349mmHg at 25°C
• Optical Rotation: [α]/D -25.5±1.5°, c = 1 in acetonitrile

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (GC); 95+%
• Empirical Formula (Hill Notation): C8H13NO4

DETAILS

Sigma Aldrich - 713473

Packaging
500 mg in glass bottle

Toronto Research Chemicals - B667390

An important β-lactone inhibitor.

REFERENCES

• Willins, D.L., et al.: J. Pharmacol. Exp. Ther., 260. 1145 (1992)
• Kaddis, F., et al.: Pharmacol. Biochem. Behav., 46, 703 (1992)