(3R,4S)-3-bromo-4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-carbonitrile

• ChemBase ID: 165012
• Molecular Formular: C12H12BrNO2
• Molecular Mass: 282.13318
• Monoisotopic Mass: 281.00514063
• SMILES: c1c(ccc2c1[C@@H]([C@H](C(O2)(C)C)Br)O)C#N
• Canonical SMILES: N#Cc1ccc2c(c1)[C@H](O)[C@H](C(O2)(C)C)Br
• InChI: InChI=1S/C12H12BrNO2/c1-12(2)11(13)10(15)8-5-7(6-14)3-4-9(8)16-12/h3-5,10-11,15H,1-2H3/t10-,11+/m0/s1
• InChIKey: PKZZJLKUYUVLMJ-WDEREUQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S)-3-bromo-4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-carbonitrile
• IUPAC Traditional name: (3R,4S)-3-bromo-4-hydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-carbonitrile
• Synonyms: trans-3-Bromo-3,4-dihydro-4-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile; 6-Cyano-trans-3-bromo-3,4-dihydro-2,2-dimethyl-2H-benzo-[b]-pyran-4-ol

Database IDs

• CAS Number: 65018-89-5
• PubChem SID: 162259145
• PubChem CID: 6932484

CALCULATED PROPERTIES

• Acid pKa: 13.042989
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.399467
• LogD (pH = 7.4): 2.399466
• Log P: 2.399467
• Molar Refractivity: 63.8139 cm^3
• Polarizability: 24.675716 Å^3
• Polar Surface Area: 53.25 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Ethyl Acetate
• Apperance: Pale Grey Solid

REFERENCES

• Pinto, I., et al.: Bioorg. Med. Chem. Lett., 3, 1743 (1993)