(2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one

• ChemBase ID: 139863
• Molecular Formular: C15H22N2O
• Molecular Mass: 246.34798
• Monoisotopic Mass: 246.17321333
• SMILES: CC(C)(C)[C@H]1N[C@H](C(=O)N1C)Cc1ccccc1
• Canonical SMILES: CN1C(=O)[C@@H](N[C@@H]1C(C)(C)C)Cc1ccccc1
• InChI: InChI=1S/C15H22N2O/c1-15(2,3)14-16-12(13(18)17(14)4)10-11-8-6-5-7-9-11/h5-9,12,14,16H,10H2,1-4H3/t12-,14-/m0/s1
• InChIKey: SKHPYKHVYFTIOI-JSGCOSHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one
• IUPAC Traditional name: (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one
• Synonyms: (2S,5S)-2-tert-Butyl-3-methyl-5-phenylmethyl-4-imidazolidinone; (2S,5S)-5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone; (2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone; (2s,5s)-(-)-2-tert-butyl-3-methyl-5-benzyl-4-imidazolidinone; (2S,5S)-2-叔丁基-3-甲基-5-苯甲基-4-咪唑烷酮; (2S,5S)-5-苄基-2-叔丁基-3-甲基-4-咪唑烷酮; (2S,5S)-(-)-2-叔丁基-3-甲基-5-苄基-4-咪唑烷酮

Database IDs

• CAS Number: 346440-54-8
• MDL Number: MFCD03426982
• PubChem SID: 162234111; 24884185
• PubChem CID: 10309834

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.6448283
• LogD (pH = 7.4): 2.9222791
• Log P: 2.927262
• Molar Refractivity: 72.4174 cm^3
• Polarizability: 28.91899 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 93-100 °C(lit.)

Safety Information

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

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C15H22N2O

DETAILS

Sigma Aldrich - 663107

Application
Metal-free OrganoCatalyst™ technology for asymmetric catalysis. Catalyzes asymmetric indole alkylations, Friedel-Crafts alkylations, and a broad range of conjugate addition reactions in high enantiomeric excess.1
Used in the 1,4-addition of electron-rich benzenes to unsaturated aldehydes, asymmetric hydride reduction of α,β-unsaturated aldehydes, and α-functionalization of aldehydes.
Packaging
1 g in glass bottle
500 mg in glass bottle
Legal Information
U.S. Pat. 6,369,243 and related patents apply. For research purposes only.
Organocatalyst is a trademark of Materia, Inc.
Protocols & Applications
Metal-free Asymmetric Catalysis using Macmillan Imidazolidinone Organocatalysts