2-[(dibenzylamino)methyl]cyclohexan-1-one hydrochloride

• ChemBase ID: 166865
• Molecular Formular: C21H26ClNO
• Molecular Mass: 343.89024
• Monoisotopic Mass: 343.17029214
• SMILES: C1CCCC(C1=O)CN(Cc1ccccc1)Cc1ccccc1.Cl
• Canonical SMILES: O=C1CCCCC1CN(Cc1ccccc1)Cc1ccccc1.Cl
• InChI: InChI=1S/C21H25NO.ClH/c23-21-14-8-7-13-20(21)17-22(15-18-9-3-1-4-10-18)16-19-11-5-2-6-12-19;/h1-6,9-12,20H,7-8,13-17H2;1H
• InChIKey: VTLHJZKKRMZUPQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(dibenzylamino)methyl]cyclohexan-1-one hydrochloride
• IUPAC Traditional name: 2-[(dibenzylamino)methyl]cyclohexan-1-one hydrochloride
• Synonyms: 2-[[Bis(phenylmethyl)amino]methyl]cyclohexanone Hydrochloride; NSC 657307; 2-[(N,N-Dibenzylamino)methyl]cyclohexanone Hydrochloride

Database IDs

• CAS Number: 102596-84-9
• PubChem SID: 162260998
• PubChem CID: 376401

CALCULATED PROPERTIES

• Acid pKa: 19.16536
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.9484255
• LogD (pH = 7.4): 3.6778233
• Log P: 4.908102
• Molar Refractivity: 95.5486 cm^3
• Polarizability: 37.42825 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 242-244°C

DETAILS

Toronto Research Chemicals - D416960

Used in asymmetric Mannich reactions by α-silyl controlled aminomethylation of ketones.

REFERENCES

• Enders, D., et al.: Synlett, 644 (20000,