Wieland-Miescher ketone

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Structural formula
Structural formula of the Wieland-Miescher ketone
Structural formula without stereochemistry
General
Surname Wieland-Miescher ketone
other names
  • 9-methyl-5 (10) octaline-1,6-dione
  • 8a-methyl-3,4,8,8a-tetrahydro-1,6 (2 H , 7 H ) -naphthalindion
Molecular formula C 11 H 14 O 2
Brief description

beige solid

External identifiers / databases
CAS number 20007-72-1
EC number 243-463-6
ECHA InfoCard 100,039,497
PubChem 89262
Wikidata Q413602
properties
Molar mass 178.23 g mol −1
Physical state

firmly

Melting point

47-50 ° C

boiling point

109–115 ° C (at 6.7 Pa )

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The Wieland-Miescher ketone is an organic chemical compound . There is a bicyclic Di ketone , which in addition to a double bond is saturated is.

The Wieland-Miescher ketone is named after its discoverers Peter Wieland and Karl Miescher , who developed it at Ciba-Geigy . The actual Wieland-Miescher ketone is obtained racemically by a Robinson annulation , but the enantiomerically pure preparation is of pharmaceutical interest .

presentation

The Wieland-Miescher ketone was first produced by a Robinson annulation . The second step of the Robinson annulation ( aldol reaction ) was carried out organocatalytically via the Eder-Sauer-Wiechert-Hajos-Parrish reaction . Enantiomerically pure ( S ) -proline was used as the organocatalyst, whereby the product could be obtained with high enantioselectivity .

Synthesis of the Wieland-Miescher ketone

The synthesis can also be carried out as a one-pot reaction . The aldol intermediate was only isolated by Hajos and Parrish and described in their patent.

use

The Wieland-Miescher ketone is of synthetic interest for the pharmaceutical industry. It serves as the starting compound for the total synthesis of steroids .

See also

Hajos Wiechert ketone

Individual evidence

  1. ↑ a b Data sheet (±) -3,4,8,8a-Tetrahydro-8a-methyl-1,6 (2H, 7H) -naphthalenedione, 98 +% from AlfaAesar, accessed on December 1, 2019 ( PDF )(JavaScript required) .
  2. ↑ a b c data sheet (±) -8a-methyl-3,4,8,8a-tetrahydro-1,6 (2H, 7H) -naphthalenedione, 98% from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ) .
  3. ↑ P. Wieland, K. Miescher: About the production of polynuclear ketones . In: Helv. Chim. Acta , 1950 , 33 , p. 2215, doi: 10.1002 / hlca.19500330730 .
  4. ↑ P. Buchschacher, A. Fürst, J. Gutzwiller: (S) -3,4,8,8a-tetrahydro-8a-methyl-1,6 (2H, 7H) -naphthalenedione In: Organic Syntheses . 63, 1985, p. 37, doi : 10.15227 / orgsyn.063.0037 ; Coll. Vol. 7, 1990, p. 368 ( PDF ).
  5. ^ T. Bui, CF Barbas: A proline-catalyzed asymmetric Robinson annulation reaction . In: Tetrahedron Letters , 2000 , 41 , pp. 6951-6954; doi: 10.1016 / S0040-4039 (00) 01180-1 .
  6. ↑ Patent DE2102623 : Werkwijze voor de bereiding van 1,3-dioxycycloalkanes. Published July 29, 1971 , Inventors: Zoltan George Hajos, David Richard Parrish. ‌
  7. ↑ Patent US3975440 : Asymmetric synthesis of organic compounds. Published August 17, 1976 , Inventors: Zoltan George Hajos, David Richard Parrish. ‌