(3R)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-2,3-dihydro-1H-1,4-benzodiazepin-2-one

• ChemBase ID: 172391
• Molecular Formular: C15H10Cl2N2O2
• Molecular Mass: 321.1581
• Monoisotopic Mass: 320.01193293
• SMILES: C1(=O)[C@H](N=C(c2c(N1)ccc(c2)Cl)c1ccccc1Cl)O
• Canonical SMILES: Clc1ccc2c(c1)C(=N[C@@H](C(=O)N2)O)c1ccccc1Cl
• InChI: InChI=1S/C15H10Cl2N2O2/c16-8-5-6-12-10(7-8)13(19-15(21)14(20)18-12)9-3-1-2-4-11(9)17/h1-7,15,21H,(H,18,20)/t15-/m1/s1
• InChIKey: DIWRORZWFLOCLC-OAHLLOKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC Traditional name: (3R)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one
• Synonyms: (R)-7-Chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one; (-)-Lorazepam; (R)-Lorazepam

Database IDs

• CAS Number: 91402-80-1
• PubChem SID: 164228301
• PubChem CID: 12049213

CALCULATED PROPERTIES

• Acid pKa: 10.606301
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.527322
• LogD (pH = 7.4): 3.527058
• Log P: 3.5273254
• Molar Refractivity: 82.6992 cm^3
• Polarizability: 31.031853 Å^3
• Polar Surface Area: 61.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L469855

(R) enantiomer of Lorazepam (L469850).

REFERENCES

• Moda, T., et al.: Bioorg. Med. Chem., 15, 7738 (2007)
• Si-Ahmed, K., et al.: Anal. Bioanal. Chem., 395, 507 (2007)