4-[(1Z)-2,6,6-trimethylcyclohex-2-en-1-ylidene]butan-2-ol

• ChemBase ID: 171711
• Molecular Formular: C13H22O
• Molecular Mass: 194.31318
• Monoisotopic Mass: 194.16706532
• SMILES: C1(CCC=C(/C/1=C\CC(C)O)C)(C)C
• Canonical SMILES: CC(C/C=C/1\C(=CCCC1(C)C)C)O
• InChI: InChI=1S/C13H22O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6,8,11,14H,5,7,9H2,1-4H3/b12-8+
• InChIKey: BNZGHWQRSDLGKB-XYOKQWHBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1Z)-2,6,6-trimethylcyclohex-2-en-1-ylidene]butan-2-ol
• IUPAC Traditional name: 4-[(1Z)-2,6,6-trimethylcyclohex-2-en-1-ylidene]butan-2-ol
• Synonyms: (4Z)-4-(2,6,6-Trimethyl-2-cyclohexen-1-ylidene)-2-butanol; (Z)-4-(2,6,6-Trimethyl-2-cyclohexen-1-ylidene)-2-butanol; (Z)-retro-α-Ionol

Database IDs

• CAS Number: 55093-47-5
• PubChem SID: 164227621
• PubChem CID: 11788800

CALCULATED PROPERTIES

• Acid pKa: 17.617287
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.8863912
• LogD (pH = 7.4): 2.8863912
• Log P: 2.8863912
• Molar Refractivity: 62.9764 cm^3
• Polarizability: 24.113565 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Yellow Oil

DETAILS

Toronto Research Chemicals - I731250

Intermediate for preparation of optically active theaspirane and β-Damascenone.

REFERENCES

• Gertraut, S., et al.: J. Agric. Food Chem., 40, 1188 (1992)
• Campagnole, M., et al.: Syn. Comm., 37, 1077 (2007).