(3aS,7aS)-3a-hydroxy-7a-methyl-octahydro-1H-indene-1,5-dione

• ChemBase ID: 150501
• Molecular Formular: C10H14O3
• Molecular Mass: 182.21636
• Monoisotopic Mass: 182.09429431
• SMILES: C[C@]12CCC(=O)C[C@]1(CCC2=O)O
• Canonical SMILES: O=C1CC[C@]2([C@](C1)(O)CCC2=O)C
• InChI: InChI=1S/C10H14O3/c1-9-4-2-7(11)6-10(9,13)5-3-8(9)12/h13H,2-6H2,1H3/t9-,10+/m1/s1
• InChIKey: PUHCDQVSBDIJTM-ZJUUUORDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,7aS)-3a-hydroxy-7a-methyl-octahydro-1H-indene-1,5-dione
• IUPAC Traditional name: (3aS,7aS)-3a-hydroxy-7a-methyl-tetrahydro-2H-indene-1,5-dione
• Synonyms: Hajos-Parrish diketone; (3aS,7aS)-(+)-Hexahydro-3a-hydroxy-7a-methyl-1,5-indandione; (3αS-cis)-Hexahydro-3α-hydroxy-7α-1H-indene-1,5(4H)-dione; (3αS,7αS)-(+)-Hexahydro-3α-hydroxy-7α-methyl-1,5-indandione; Hajos-Parrish 二酮; (S)-(+)-六氢-3a-羟基-7a-甲基-1H-茚-1,5(6H)-二酮

Database IDs

• CAS Number: 33879-04-8
• MDL Number: MFCD00135412
• Beilstein Number: 2447128
• PubChem SID: 24857948; 162244662
• PubChem CID: 2724501

CALCULATED PROPERTIES

• Acid pKa: 13.981713
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.67244667
• LogD (pH = 7.4): 0.67244655
• Log P: 0.67244667
• Molar Refractivity: 46.6858 cm^3
• Polarizability: 18.493624 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 116-118 °C(lit.); 116118°C
• Optical Rotation: [α]19/D +55°, c = 1 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C10H14O3
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 297933

Packaging
1 g in glass bottle

Toronto Research Chemicals - H294025

A useful synthetic intermediate.

REFERENCES

• Rohrig, S., et al.: Tetrahedron, 54(14)
• 3439 (1998)