(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one

• ChemBase ID: 139838
• Molecular Formular: C16H18N2O2
• Molecular Mass: 270.32632
• Monoisotopic Mass: 270.13682783
• SMILES: Cc1ccc(o1)[C@H]1N[C@H](C(=O)N1C)Cc1ccccc1
• Canonical SMILES: Cc1ccc(o1)[C@H]1N[C@H](C(=O)N1C)Cc1ccccc1
• InChI: InChI=1S/C16H18N2O2/c1-11-8-9-14(20-11)15-17-13(16(19)18(15)2)10-12-6-4-3-5-7-12/h3-9,13,15,17H,10H2,1-2H3/t13-,15-/m0/s1
• InChIKey: IQIMPHPFMHVWBZ-ZFWWWQNUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one
• IUPAC Traditional name: (2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one
• Synonyms: (2S,5S)-3-Methyl-2-(5-methyl-2-furanyl)-5-(phenylmethyl)-4-imidazolidinone; (2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone; (2s,5s)-(-)-5-benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone; (2S,5S)-3-甲基-2-(5-甲基-2-呋喃基)-5-(苯甲基)-4-咪唑烷酮; (2S,5S)-(-)-5-苄基-3-甲基-2-(5-甲基-2-呋喃基)-4-咪唑烷酮

Database IDs

• CAS Number: 415678-40-9
• MDL Number: MFCD08457653
• PubChem SID: 24884991; 162234086
• PubChem CID: 11303220

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.281614
• LogD (pH = 7.4): 2.2891424
• Log P: 2.2892392
• Molar Refractivity: 76.4283 cm^3
• Polarizability: 29.758656 Å^3
• Polar Surface Area: 45.48 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: >110 °C; >230 °F
• Refractive Index: n20/D 1.5598

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-36-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: 95%; 98%
• Empirical Formula (Hill Notation): C16H18N2O2

DETAILS

Sigma Aldrich - 668540

Application
Highly selective organocatalyst for the Diels-Alder reaction with simple α,β-unsaturated ketones.4
Catalyst for:
• Enantioselective organocatalytic transfer hydrogenation of cycloalkenones with tert-Bu Hantzsch ester as source of hydrogen1
• Alkylation of indoles with an α,β-disubstituted α,β-unsaturated aldehyde in the enantioselective preparation of a selective serotonin reuptake inhibitor2
• MacMillan reaction3
Packaging
1 g in glass bottle
250 mg in glass bottle
Legal Information
U.S. Pat. 6,369,243 and related patents apply. For research purposes only.
Protocols & Applications
Metal-free Asymmetric Catalysis using Macmillan Imidazolidinone Organocatalysts