8a-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-1,6-dione

• ChemBase ID: 130186
• Molecular Formular: C11H14O2
• Molecular Mass: 178.22766
• Monoisotopic Mass: 178.09937969
• SMILES: CC12CCC(=O)C=C1CCCC2=O
• Canonical SMILES: O=C1CCC2(C(=C1)CCCC2=O)C
• InChI: InChI=1S/C11H14O2/c1-11-6-5-9(12)7-8(11)3-2-4-10(11)13/h7H,2-6H2,1H3
• InChIKey: DNHDRUMZDHWHKG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8a-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-1,6-dione
• IUPAC Traditional name: wieland-miescher ketone
• Synonyms: (+/-)-9-Methyl-DELTA(5,10)-octalin-1,6-dione; Wieland-Miescher ketone, racemic; (±)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione; Wieland–Miescher ketone; (±)-9-Methyl-5(10)-octaline-1,6-dione; Miescher-Wieland ketone; Wieland-Miescher ketone; (±)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione; (±)-3,4,8,8a-四氢-8a-甲基-1,6(2H,7H)-萘二酮; (±)-9-甲基-5(10)-辛-1,6-二酮; Wieland-Miescher 酮; 魏兰德-米歇尔酮; (±)-8a-甲基-3,4,8,8a-四氢-1,6(2H,7H)-萘二酮

Database IDs

• CAS Number: 20007-72-1
• EC Number: 243-463-6
• MDL Number: MFCD00001687
• Beilstein Number: 3201286
• PubChem SID: 162224470; 24897092
• PubChem CID: 89262
• Wikipedia Title: Wieland–Miescher_ketone

CALCULATED PROPERTIES

• Acid pKa: 17.79769
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.0745733
• LogD (pH = 7.4): 2.0745733
• Log P: 2.0745733
• Molar Refractivity: 50.7394 cm^3
• Polarizability: 19.4364 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 47-50 °C(lit.); 47–50 °C; 47-50°C

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%; 98+%
• Empirical Formula (Hill Notation): C11H14O2

DETAILS

Sigma Aldrich - M65157

Packaging
5, 10 g in glass bottle

REFERENCES

• The enolate formed with LDA undergoes a double Michael reaction with methyl acrylate to give a tricyclic product: Tetrahedron, 51, 9891 (1995):