tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

• ChemBase ID: 147892
• Molecular Formular: C14H19NO3
• Molecular Mass: 249.30556
• Monoisotopic Mass: 249.13649347
• SMILES: CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C=O
• Canonical SMILES: O=C[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C14H19NO3/c1-14(2,3)18-13(17)15-12(10-16)9-11-7-5-4-6-8-11/h4-8,10,12H,9H2,1-3H3,(H,15,17)/t12-/m0/s1
• InChIKey: ZJTYRNPLVNMVPQ-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate
• Synonyms: (S)-(-)-2-(tert-Butoxycarbonylamino)-3-phenylpropanal; N-Boc-L-phenylalaninal; N-[(1S)-1-Formyl-2-phenylethyl]carbamic Acid 1,1-Dimethylethyl Ester; (S)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanal; Boc-L-phenylalaninal; Boc-phenylalaninal; N-(tert-Butoxycarbonyl)phenylalaninal; N-Boc-phenylalaninal; (S)-(-)-2-(叔丁氧羰基氨基)-3-苯丙醛; N-Boc-L-苯丙氨醛

Database IDs

• CAS Number: 72155-45-4
• MDL Number: MFCD00143854
• PubChem SID: 24870581; 162242073
• PubChem CID: 6998013

CALCULATED PROPERTIES

• Acid pKa: 13.766864
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.411096
• LogD (pH = 7.4): 2.411096
• Log P: 2.411096
• Molar Refractivity: 69.0639 cm^3
• Polarizability: 27.034893 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Diethyl Ether
• Apperance: White Solid
• Melting Point: 86-88 °C(lit.)
• Optical Rotation: [α]20/D -47°, c = 0.5 in methanol

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CTSK(1513)

Product Information

• Purity: 97%
• Linear Formula: C6H5CH2CH[NHCO2C(CH3)3]CHO

DETAILS

Sigma Aldrich - 469297

Packaging
250 mg in glass bottle
Application
Intermediate for the synthesis of hydroxyethylene dipeptide isosteres that have enzyme inhibition properties.1

Toronto Research Chemicals - B661520

An amino aldehyde. A potent human cathepsin K inhibitor.

REFERENCES

• Catalano, J.G., et al.: Bioorg. Med. Chem. Lett., 14, 275 (2004)
• Pan, X., et al.: Bioorg. Med. Chem., 14, 2771 (2006).