(2E)-but-2-enedioic acid; 2-(tert-butylamino)-1-(3,5-dichlorophenyl)propan-1-one

• ChemBase ID: 164115
• Molecular Formular: C17H21Cl2NO5
• Molecular Mass: 390.25834
• Monoisotopic Mass: 389.07967814
• SMILES: c1c(cc(cc1C(=O)C(NC(C)(C)C)C)Cl)Cl.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: Clc1cc(Cl)cc(c1)C(=O)C(NC(C)(C)C)C.OC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C13H17Cl2NO.C4H4O4/c1-8(16-13(2,3)4)12(17)9-5-10(14)7-11(15)6-9;5-3(6)1-2-4(7)8/h5-8,16H,1-4H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
• InChIKey: MGHPTSVYSLXGEG-WLHGVMLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid; 2-(tert-butylamino)-1-(3,5-dichlorophenyl)propan-1-one
• IUPAC Traditional name: 2-(tert-butylamino)-1-(3,5-dichlorophenyl)propan-1-one; fumaric acid
• Synonyms: 1-(3,5-Dichlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone (2E)-2-Butenedioate; 5-Chloro Bupropion Fumarate

Database IDs

• CAS Number: 1193779-50-8
• PubChem SID: 162258250
• PubChem CID: 71314698

CALCULATED PROPERTIES

• Acid pKa: 18.138792
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.3202515
• LogD (pH = 7.4): 3.0527375
• Log P: 3.8701572
• Molar Refractivity: 72.5042 cm^3
• Polarizability: 28.539701 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C364765

A 5-chloro substitued analogue of Buproprion (B689625) used in the preparation of compounds for indirect dopamine agonist pharmacotherapy for treating cocaine, methamphetamine, nicotine, and other drugs of abuse addiction.

REFERENCES

• Carroll, F.I. et al.: J. Med. Chem., 52, 6768 (2009)