(3S,5S)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylidenecyclohexan-1-one

• ChemBase ID: 162218
• Molecular Formular: C19H38O3Si2
• Molecular Mass: 370.67422
• Monoisotopic Mass: 370.23594814
• SMILES: C1[C@H](C[C@@H](C(=C)C1=O)O[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C
• Canonical SMILES: C=C1C(=O)C[C@H](C[C@@H]1O[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C19H38O3Si2/c1-14-16(20)12-15(21-23(8,9)18(2,3)4)13-17(14)22-24(10,11)19(5,6)7/h15,17H,1,12-13H2,2-11H3/t15-,17+/m1/s1
• InChIKey: HMIPXZOWGMCFDW-WBVHZDCISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,5S)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylidenecyclohexan-1-one
• IUPAC Traditional name: (3S,5S)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylidenecyclohexan-1-one
• Synonyms: (3S-trans)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylene-cyclohexanone; (3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methylene-cyclohexanone

Database IDs

• CAS Number: 190062-19-2
• PubChem SID: 162256353
• PubChem CID: 10833001

CALCULATED PROPERTIES

• Acid pKa: 18.650328
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 5.1753
• LogD (pH = 7.4): 5.1753
• Log P: 5.1753
• Molar Refractivity: 95.3089 cm^3
• Polarizability: 42.07382 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - B415785

Intermediate in the preparation of Dihydroxyvitamin D3 and associated metabolites.

REFERENCES

• Lee, N., et al.: Biochem., 36, 9429 (1997)