3-ethoxycyclohex-2-en-1-one

• ChemBase ID: 89763
• Molecular Formular: C8H12O2
• Molecular Mass: 140.17968
• Monoisotopic Mass: 140.08372962
• SMILES: O=C1C=C(CCC1)OCC
• Canonical SMILES: CCOC1=CC(=O)CCC1
• InChI: InChI=1S/C8H12O2/c1-2-10-8-5-3-4-7(9)6-8/h6H,2-5H2,1H3
• InChIKey: JWCFJPLIRVYENQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethoxycyclohex-2-en-1-one
• IUPAC Traditional name: 3-ethoxycyclohex-2-en-1-one
• Synonyms: 3-Ethoxy-2-cyclohexenone; 3-Ethoxy-1-oxocyclohex-2-ene; 3-Ethoxycyclohex-2-en-1-one; 3-Ethoxy-2-cyclohexen-1-one; 3-乙氧基-2-环己烯-1-酮

Database IDs

• CAS Number: 5323-87-5
• EC Number: 226-190-7
• MDL Number: MFCD00001580
• Beilstein Number: 2042049
• PubChem SID: 24894556; 162076619
• PubChem CID: 79216

CALCULATED PROPERTIES

• Acid pKa: 17.903803
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.1288987
• LogD (pH = 7.4): 1.1288987
• Log P: 1.1288987
• Molar Refractivity: 40.8868 cm^3
• Polarizability: 15.260673 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 76-78 °C/1 mmHg(lit.); 76-78°C/1mm; 76-78°C/1mm
• Flash Point: >107°C; 107 °C; 107°C(224°F); 224.6 °F
• Density: 0.963 g/mL at 25 °C(lit.); 1.03; 1.04
• Refractive Index: 1.506; 1.5060; n20/D 1.504(lit.)

Safety Information

• Storage Warning: Irritant/Keep Cold
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 99%
• Linear Formula: C2H5OC6H7(=O)

DETAILS

Sigma Aldrich - E4453

Packaging
10, 25 g in glass bottle

REFERENCES

• Useful intermediate for the preparation of 3-alkyl- or aryl-2-cyclohexen-1-ones, by addition of organometallic reagents and subsequent hydrolysis: J. Am. Chem. Soc., 70, 2174 (1948); 72, 1645 (1950); Helv. Chim. Acta, 36, 482 (1963). For an example of this transformation in the total synthesis of axane sesquiterpenoids, see: J. Org. Chem., 61, 473 (1996):
  
• Under conditions of kinetic enolate formation (LDA), alkylation occurs at the 6-position: the Stork-Danheiser kinetic alkylation procedure, which has found extensive use in alicyclic synthesis: J. Org. Chem., 38, 1775 (1973); Org. Synth. Coll., 7, 208 (1990) and references therein.