(5S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one hydrochloride

• ChemBase ID: 145038
• Molecular Formular: C13H19ClN2O
• Molecular Mass: 254.75576
• Monoisotopic Mass: 254.11859092
• SMILES: CC1(N(C(=O)[C@@H](N1)Cc1ccccc1)C)C.Cl
• Canonical SMILES: O=C1[C@H](Cc2ccccc2)NC(N1C)(C)C.Cl
• InChI: InChI=1S/C13H18N2O.ClH/c1-13(2)14-11(12(16)15(13)3)9-10-7-5-4-6-8-10;/h4-8,11,14H,9H2,1-3H3;1H/t11-;/m0./s1
• InChIKey: YIYFEXGDFJLJGM-MERQFXBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one hydrochloride
• IUPAC Traditional name: (5S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one hydrochloride
• Synonyms: (5S)-(-)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone monohydrochloride; (5s)-(-)-2,2,3-trimethyl-5-benzyl-4-imidazolidinone monohydrochloride; (5S)-(-)-2,2,3-三甲基-5-苄基-4-咪唑啉酮 单盐酸盐

Database IDs

• CAS Number: 278173-23-2
• MDL Number: MFCD03426983
• PubChem SID: 24880521; 162239248
• PubChem CID: 9834882

CALCULATED PROPERTIES

• H Donor: 1
• LogD (pH = 5.5): 1.3394761
• LogD (pH = 7.4): 1.5630312
• Log P: 1.5667765
• Molar Refractivity: 64.2111 cm^3
• Polarizability: 25.229525 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• H Acceptors: 2

PROPERTIES

Physical Property

• Melting Point: 157-161 °C(lit.)
• Optical Rotation: [α]20/D -67°, c = 1 in H2O

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): C13H18N2O · HCl

DETAILS

Sigma Aldrich - 569763

Application
Metal-free OrganoCatalyst technology for asymmetric catalysis. Catalyzes asymmetric Diels-Alder reactions, 1,3-dipolar additions and pyrrole alkylations in high enantiomeric excess.1,2,3
Used in first highly enantioselective organocatalytic Diels-Alder reaction and 1,3-dipolar addition.
Packaging
2 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.
Protocols & Applications
Metal-free Asymmetric Catalysis using Macmillan Imidazolidinone Organocatalysts