(3S)-3-[(triphenylmethyl)amino]oxetan-2-one

• ChemBase ID: 152480
• Molecular Formular: C22H19NO2
• Molecular Mass: 329.39176
• Monoisotopic Mass: 329.14157885
• SMILES: c1ccc(cc1)C(c1ccccc1)(c1ccccc1)N[C@H]1COC1=O
• Canonical SMILES: O=C1OC[C@@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C22H19NO2/c24-21-20(16-25-21)23-22(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-15,20,23H,16H2/t20-/m0/s1
• InChIKey: WKOYUOGPQDPOFV-FQEVSTJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(triphenylmethyl)amino]oxetan-2-one
• IUPAC Traditional name: (3S)-3-[(triphenylmethyl)amino]oxetan-2-one
• Synonyms: (S)-3-(Tritylamino)-2-oxetanone; N-Trityl-L-serine lactone; (S)-3-(三苯甲基氨基)-2-氧杂环丁烷酮; N-三苯甲基-L-丝氨酸内酯

Database IDs

• CAS Number: 88109-06-2
• MDL Number: MFCD00270148
• Beilstein Number: 40996
• PubChem SID: 24889894; 162246625
• PubChem CID: 10892835

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.6235247
• LogD (pH = 7.4): 4.628324
• Log P: 4.6283855
• Molar Refractivity: 98.3736 cm^3
• Polarizability: 38.472515 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 191-196 °C (dec.)
• Optical Rotation: [α]20/D -71±2°, c = 0.5% in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (sum of enantiomers, TLC)
• Empirical Formula (Hill Notation): C22H19NO2

DETAILS

Sigma Aldrich - 93470

Other Notes
Chiral building block for preparing unnatural amino acids with nucleophiles1
Packaging
1 g in glass bottle