(5S)-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one

• ChemBase ID: 146012
• Molecular Formular: C24H23NO2
• Molecular Mass: 357.44492
• Monoisotopic Mass: 357.17287898
• SMILES: c1ccc(cc1)C(c1ccccc1)(c1ccccc1)OC[C@@H]1CCC(=O)N1
• Canonical SMILES: O=C1CC[C@H](N1)COC(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C24H23NO2/c26-23-17-16-22(25-23)18-27-24(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-15,22H,16-18H2,(H,25,26)/t22-/m0/s1
• InChIKey: FQSSRLVFPQIRJK-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one
• IUPAC Traditional name: (5S)-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one
• Synonyms: (S)-(+)-5-(Trityloxymethyl)-2-pyrrolidinone; (S)-(+)-5-(三苯甲基氧代甲基)-2-吡咯烷酮

Database IDs

• CAS Number: 105526-85-0
• MDL Number: MFCD00075592
• PubChem SID: 162240212; 24863281
• PubChem CID: 2733644

CALCULATED PROPERTIES

• Acid pKa: 14.391566
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.5901375
• LogD (pH = 7.4): 4.5901375
• Log P: 4.5901375
• Molar Refractivity: 108.0218 cm^3
• Polarizability: 41.755337 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 164-166 °C(lit.)
• Optical Rotation: [α]20/D +15°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C24H23NO2

DETAILS

Sigma Aldrich - 374113

Packaging
5 g in glass bottle
Application
Used in asymmetric Diels-Alder reactions1 and asymmetric conjugate additions.2