(2R)-1-benzoyl-2-tert-butyl-3-methylimidazolidin-4-one

• ChemBase ID: 138613
• Molecular Formular: C15H20N2O2
• Molecular Mass: 260.3315
• Monoisotopic Mass: 260.15247789
• SMILES: CC(C)(C)[C@@H]1N(C(=O)CN1C(=O)c1ccccc1)C
• Canonical SMILES: O=C1CN([C@@H](N1C)C(C)(C)C)C(=O)c1ccccc1
• InChI: InChI=1S/C15H20N2O2/c1-15(2,3)14-16(4)12(18)10-17(14)13(19)11-8-6-5-7-9-11/h5-9,14H,10H2,1-4H3/t14-/m1/s1
• InChIKey: QMSFVKQUCYMTLD-CQSZACIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-benzoyl-2-tert-butyl-3-methylimidazolidin-4-one
• IUPAC Traditional name: (2R)-1-benzoyl-2-tert-butyl-3-methylimidazolidin-4-one
• Synonyms: (R)-1-Benzoyl-2-tert-butyl-3-methyl-4-imidazolidinone; (R)-1-苯甲酰-2-叔丁基-3-甲基-4-咪唑烷酮

Database IDs

• CAS Number: 101055-57-6
• MDL Number: MFCD00066237
• Beilstein Number: 3652380
• PubChem SID: 162232866
• PubChem CID: 688129

CALCULATED PROPERTIES

• Acid pKa: 18.249954
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.166288
• LogD (pH = 7.4): 2.1662881
• Log P: 2.1662881
• Molar Refractivity: 73.5409 cm^3
• Polarizability: 28.37239 Å^3
• Polar Surface Area: 40.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 145-147 °C
• Optical Rotation: [α]20/D -128±2°, c = 1% in methylene chloride

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC); 99%
• Grade: puriss.
• Optical Purity: ee: 99% (GLC); enantiomeric ratio: ≥99:1 (HPLC)
• Empirical Formula (Hill Notation): C15H20N2O2

DETAILS

Sigma Aldrich - 12931

Other Notes
Chiral glycine derivative used for the synthesis of amino acids. The enolate is alkylated with relative topicity lk to give the l (trans) isomer1,2,3,4; Stereoselective bromination5