ethyl (2R)-2-hydroxy-4-(2H5)phenylbutanoate

• ChemBase ID: 171063
• Molecular Formular: C12H16O3
• Molecular Mass: 208.25364
• Monoisotopic Mass: 208.10994437
• SMILES: c1(CC[C@H](C(=O)OCC)O)ccccc1
• Canonical SMILES: CCOC(=O)[C@@H](CCc1ccccc1)O
• InChI: InChI=1S/C12H16O3/c1-2-15-12(14)11(13)9-8-10-6-4-3-5-7-10/h3-7,11,13H,2,8-9H2,1H3/t11-/m1/s1
• InChIKey: ZJYKSSGYDPNKQS-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R)-2-hydroxy-4-(^2H₅)phenylbutanoate
• IUPAC Traditional name: ethyl (2R)-2-hydroxy-4-(^2H₅)phenylbutanoate
• Synonyms: (αR)-α-Hydroxybenzenebutanoic Acid-d5 Ethyl Ester; (R)-Ethyl 2-Hydroxy-4-phenylbutanoate-d5; Ethyl (R)-α-Hydroxybenzenebutanoate-d5; Ethyl 2(R)-hydroxy-4-phenylbutyrate-d5; (R)-2-Hydroxy-4-phenylbutyric Acid-d5 Ethyl Ester

Database IDs

• CAS Number: 1286413-90-8
• PubChem SID: 164226973
• PubChem CID: 71749244

CALCULATED PROPERTIES

• Acid pKa: 12.695693
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.1317675
• LogD (pH = 7.4): 2.1317654
• Log P: 2.1317675
• Molar Refractivity: 57.5775 cm^3
• Polarizability: 22.781853 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane

DETAILS

Toronto Research Chemicals - H949098

Used in the preparation of benzothiophenes, benzofurans, and indoles useful in the treatment of insulin resistance and hyperglycemia.

REFERENCES

• Chang, A., et al.: Diabetes, 32, 830 (1983)
• Goldstein, B. et al.: Cell Biochem., 48, 33 (1983)
• Sredy, J., et al.: Metabolism, 44, 1074 (1983)