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

• ChemBase ID: 152663
• Molecular Formular: C11H14O2
• Molecular Mass: 178.22766
• Monoisotopic Mass: 178.09937969
• SMILES: C[C@@]12CCC(=O)C=C1CCCC2=O
• Canonical SMILES: O=C1CC[C@@]2(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/t11-/m1/s1
• InChIKey: DNHDRUMZDHWHKG-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8aR)-8a-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-1,6-dione
• IUPAC Traditional name: (8aR)-8a-methyl-3,4,7,8-tetrahydro-2H-naphthalene-1,6-dione
• Synonyms: (R)-(-)-9-Methyl-5(10)-octaline-1,6-dione; (R)-Miescher-Wieland ketone; (R)-(-)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione; (R)-魏兰德-米歇尔酮; (R)-(-)-9-甲基-5(10)-辛-1,6-二酮; (R)-(-)-8a-甲基-3,4,8,8a-四氢-1,6(2H,7H)-萘二酮

Database IDs

• CAS Number: 100348-93-4
• MDL Number: MFCD00063004
• Beilstein Number: 2050425
• PubChem SID: 162246806; 24885651
• PubChem CID: 736070

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: 49-51 °C
• Optical Rotation: [α]20/D -98±2°, c = 1.1% in benzene

Safety Information

• German water hazard class: 3
• Safety Statements: 22-24/25
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC)
• Empirical Formula (Hill Notation): C11H14O2

DETAILS

Sigma Aldrich - 68169

Other Notes
Building block for synthesizing ent-steroids using procedures described for the enantiomer. Synthesis of other chiral natural products1,2,3,4
Packaging
500 mg in glass bottle