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

• ChemBase ID: 165020
• Molecular Formular: C16H20N2O2
• Molecular Mass: 272.3422
• Monoisotopic Mass: 272.15247789
• SMILES: c1c(cc2c(c1)OC([C@@H]([C@H]2N1CCCC1)O)(C)C)C#N
• Canonical SMILES: O[C@@H]1[C@@H](N2CCCC2)c2cc(ccc2OC1(C)C)C#N
• InChI: InChI=1S/C16H20N2O2/c1-16(2)15(19)14(18-7-3-4-8-18)12-9-11(10-17)5-6-13(12)20-16/h5-6,9,14-15,19H,3-4,7-8H2,1-2H3/t14-,15+/m0/s1
• InChIKey: UCEHSLHTSICLRD-LSDHHAIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S)-3-hydroxy-2,2-dimethyl-4-(pyrrolidin-1-yl)-3,4-dihydro-2H-1-benzopyran-6-carbonitrile
• IUPAC Traditional name: (3R,4S)-3-hydroxy-2,2-dimethyl-4-(pyrrolidin-1-yl)-3,4-dihydro-1-benzopyran-6-carbonitrile
• Synonyms: (3R,4S)-rel-3,4-Dihydro-3-hydroxy-2,2-dimethyl-4-(1-pyrrolidinyl)-2H-1-benzopyran-6-carbonitrile; 6-Cyano-3,4-dihydro-2,2-dimethyl-trans-4-(1-pyrrolidinyl)-2H-benzo-[b]-pyrano-3-ol

Database IDs

• CAS Number: 75611-78-8
• PubChem SID: 162259153
• PubChem CID: 22839067

CALCULATED PROPERTIES

• Acid pKa: 13.272445
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.8078947
• LogD (pH = 7.4): 0.9582736
• Log P: 1.9739238
• Molar Refractivity: 77.0472 cm^3
• Polarizability: 30.08932 Å^3
• Polar Surface Area: 56.49 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMF
• Apperance: Brown Solid

DETAILS

Toronto Research Chemicals - C979100

An analogue of Cromakalin, which causes vasodilation by activation of potassim channels.

REFERENCES

• Ashwood, V., et al.: J. Med. Chem., 29, 2194 (1986)