(1R)-1-(3,4-dimethoxyphenyl)-2-iodoethan-1-ol

• ChemBase ID: 171677
• Molecular Formular: C10H13IO3
• Molecular Mass: 308.11289
• Monoisotopic Mass: 307.99094228
• SMILES: c1(c(ccc(c1)[C@H](CI)O)OC)OC
• Canonical SMILES: IC[C@@H](c1ccc(c(c1)OC)OC)O
• InChI: InChI=1S/C10H13IO3/c1-13-9-4-3-7(8(12)6-11)5-10(9)14-2/h3-5,8,12H,6H2,1-2H3/t8-/m0/s1
• InChIKey: QXUYTOYFDIQESZ-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-1-(3,4-dimethoxyphenyl)-2-iodoethan-1-ol
• IUPAC Traditional name: (1R)-1-(3,4-dimethoxyphenyl)-2-iodoethanol
• Synonyms: (αR)-α-(Iodomethyl)-3,4-dimethoxybenzenemethanol

Database IDs

• CAS Number: 833353-17-6
• PubChem SID: 164227587
• PubChem CID: 11197582

CALCULATED PROPERTIES

• Acid pKa: 13.681188
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.074676
• LogD (pH = 7.4): 2.0746758
• Log P: 2.074676
• Molar Refractivity: 63.2 cm^3
• Polarizability: 24.737452 Å^3
• Polar Surface Area: 38.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - I708380

(αR)-α-(Iodomethyl)-3,4-dimethoxy-benzenemethanol is used in the preparation of (R)-Isoprenaline, (R)-Norfluoxetine and (R)-Fluoxetine using stereoselective dihydroxylation method as key synthetic step.

REFERENCES

• Zerbe, R., et al.: J. Pharmacol. Exp. Ther., 232, 139 (1985)
• Bracher, F., et al.: Bioorg. Med. Chem., 4, 877 (1985)
• Robertson, D., et al.: J. Med. Chem., 31, 1412 (1985)