Home > Compound List > Compound details
33878-99-8 molecular structure
click picture or here to close

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

ChemBase ID: 87851
Molecular Formular: C11H14O2
Molecular Mass: 178.22766
Monoisotopic Mass: 178.09937969
SMILES and InChIs

SMILES:
O=C1C=C2CCCC(=O)[C@]2(CC1)C
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-/m0/s1
InChIKey:
DNHDRUMZDHWHKG-NSHDSACASA-N

Cite this record

CBID:87851 http://www.chembase.cn/molecule-87851.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(8aS)-8a-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-1,6-dione
IUPAC Traditional name
(8aS)-8a-methyl-3,4,7,8-tetrahydro-2H-naphthalene-1,6-dione
Synonyms
(S)-(+)-9-Methyl-5(10)-octaline-1,6-dione
(S)-Miescher-Wieland ketone
(S)-(+)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione
Wieland-Miescher ketone
(S)-(+)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione
(S)-(+)-9-Methyl-Δ(5,10)-octalin-1,6-dione
(S)-Wieland-Miescher ketone
(8aS)-(+)-8a-Methyl-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione
(S)-Miescher-Wieland 酮
(S)-(+)-8a-甲基-3,4,8,8a-四氢-1,6(2H,7H)-萘二酮
Wieland-Miescher 酮
(S)-(+)-3,4,8,8a-四氢-8a-甲基-1,6(2H,7H)-萘二酮
(S)-(+)-3,4,8,8a-四氢-8a-甲基-1,6-(2H,7H)-萘二酮
CAS Number
33878-99-8
MDL Number
MFCD00213797
Beilstein Number
1569979
PubChem SID
162074891
24867341
PubChem CID
736069

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 17.79769  H Acceptors
H Donor LogD (pH = 5.5) 2.0745733 
LogD (pH = 7.4) 2.0745733  Log P 2.0745733 
Molar Refractivity 50.7394 cm3 Polarizability 19.4364 Å3
Polar Surface Area 34.14 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
48-52°C expand Show data source
50-51°C expand Show data source
50-52 °C(lit.) expand Show data source
Optical Rotation
[α]20/D +98°, c = 1.1 in benzene expand Show data source
+100 (c=1 in benzene) expand Show data source
Storage Warning
Irritant expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
98% expand Show data source
99% expand Show data source
Empirical Formula (Hill Notation)
C11H14O2 expand Show data source
Classification
Derivatives & analogs of Natural Compounds expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 437026 external link
Application
Key intermediate in the total synthesis of the macrocyclic diterpene lactone, (+)-cleomeolide.1,2 Chiral building block for enantioselective approaches to the A and C rings of taxol.3,4,5 Used to study selective hydrogenations of the carbon-carbon double bonds in α,β-unsaturated ketones with a new class of palladium complexes as catalysts.6

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Key intermediate in enantioselective steroid syntheses; see, e.g.: Angew. Chem. Int. Ed., 10, 496 (1971); Chem. Ber., 106, 3636 (1973); J. Org. Chem., 45, 2204 (1980).
  • • For an example of use in synthesis of a diterpene, see: J. Chem. Soc., Perkin 1, 2151 (1986), and of taxane intermediates: J. Org. Chem., 57, 3274 (1992).
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle