(2S)-1-[(diphenylmethylidene)amino]-2-(hydroxymethyl)-1-methylpyrrolidin-1-ium iodide

• ChemBase ID: 173598
• Molecular Formular: C19H23IN2O
• Molecular Mass: 422.30319
• Monoisotopic Mass: 422.08551137
• SMILES: C1CC[N+]([C@@H]1CO)(C)/N=C(/c1ccccc1)\c1ccccc1.[I-]
• Canonical SMILES: OC[C@@H]1CCC[N+]1(C)/N=C(/c1ccccc1)\c1ccccc1.[I-]
• InChI: InChI=1S/C19H23N2O.HI/c1-21(14-8-13-18(21)15-22)20-19(16-9-4-2-5-10-16)17-11-6-3-7-12-17;/h2-7,9-12,18,22H,8,13-15H2,1H3;1H/q+1;/p-1/t18-,21?;/m0./s1
• InChIKey: SEFOZSLXHJNIQH-YKIRIDQTSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(diphenylmethylidene)amino]-2-(hydroxymethyl)-1-methylpyrrolidin-1-ium iodide
• IUPAC Traditional name: (2S)-1-[(diphenylmethylidene)amino]-2-(hydroxymethyl)-1-methylpyrrolidin-1-ium iodide
• Synonyms: (2S)-1-Methyl-1-[N-(diphenylmethylene)]-2-hydroxymethylpyrrolidine, Hydrazonium Iodide

Database IDs

• CAS Number: 168128-27-6
• PubChem SID: 164229508
• PubChem CID: 11112636

CALCULATED PROPERTIES

• Acid pKa: 13.535595
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.450338
• LogD (pH = 7.4): 0.45034397
• Log P: 0.45033795
• Molar Refractivity: 91.9842 cm^3
• Polarizability: 34.89213 Å^3
• Polar Surface Area: 32.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M303690

A specifically designed chiral catalyst in the alkylation of aromatic imines under solid-liquid phase-transfer conditions leading to optically active primary amines.

REFERENCES

• Eddine, J.J. and Cherqaoui, M.: Tetrahedron Asymmetry, 6, 6, 1225 (1995)