1,3-diethyl 2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-(2H3)methylpropanedioate

• ChemBase ID: 167330
• Molecular Formular: C20H24ClNO4
• Molecular Mass: 377.86186
• Monoisotopic Mass: 377.13938593
• SMILES: c1c(cc2c(c1)[nH]c1c2CCC(C1)C(C(=O)OCC)(C(=O)OCC)C)Cl
• Canonical SMILES: CCOC(=O)C(C1CCc2c(C1)[nH]c1c2cc(cc1)Cl)(C(=O)OCC)C
• InChI: InChI=1S/C20H24ClNO4/c1-4-25-18(23)20(3,19(24)26-5-2)12-6-8-14-15-11-13(21)7-9-16(15)22-17(14)10-12/h7,9,11-12,22H,4-6,8,10H2,1-3H3
• InChIKey: XWJZVIIPTMHYNQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diethyl 2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-(^2H₃)methylpropanedioate
• IUPAC Traditional name: 1,3-diethyl 2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-(^2H₃)methylpropanedioate
• Synonyms: (6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)methyl-propanedioic Acid Diethyl Ester; Diethyl-(6-chloro1,2,3,4-tetrahydro-2-carbazolyl)methyl-d3 Malonate

Database IDs

• PubChem SID: 162261463
• PubChem CID: 45039002

CALCULATED PROPERTIES

• Acid pKa: 16.807062
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.5998435
• LogD (pH = 7.4): 4.5998435
• Log P: 4.5998435
• Molar Refractivity: 100.1061 cm^3
• Polarizability: 40.218365 Å^3
• Polar Surface Area: 68.39 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White Powder

DETAILS

Toronto Research Chemicals - D444122

A labelled intermediate in the synthesis of Caprofen-d3.

REFERENCES

• Randall, L.O., et al.: Arch. Int. Pharmacodyn., 220,94 (1976)
• Yu, T.F., et al.: J. Clin. Pharmacol., 20, 347 (1976)
• O’Brien, W.M., et al.: Pharmacotherapy, 7, 16 (1976)