100348-93-4

Usage

Uses

Used in Pharmaceutical Industry:
R(-)-8A-METHYL-3,4,8,8A-TETRAHYDRO-1,6(2H,7H)-NAPHTHALENEDIONE is used as a key intermediate in the synthesis of various pharmaceutical drugs. Its unique structure allows for the development of new and innovative medications with potential therapeutic benefits.
Used in Chemical Industry:
R(-)-8A-METHYL-3,4,8,8A-TETRAHYDRO-1,6(2H,7H)-NAPHTHALENEDIONE is used as a reagent in various chemical processes. Its versatility and reactivity make it a valuable component in the synthesis of complex organic molecules, contributing to the advancement of the chemical industry.
Used in Natural Product Synthesis:
R(-)-8A-METHYL-3,4,8,8A-TETRAHYDRO-1,6(2H,7H)-NAPHTHALENEDIONE is used as a building block in the synthesis of biologically active natural products. Its unique properties enable the creation of novel compounds with potential applications in various fields, including medicine, agriculture, and environmental science.

InChI:InChI=1/C11H14O2/c1-11-6-5-9(12)7-8(11)3-2-4-10(11)13/h7H,2-6H2,1H3/t11-/m1/s1

Upstream product

• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 542-05-2 acetonedicarboxylic acid 
• 3299-38-5 4-(diethylamino)butan-2-one 
• 43025-83-8 diethyl-methyl-(3-oxo-butyl)-ammonium; iodide 
• 5073-65-4 2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione 
• 78-94-4 methyl vinyl ketone 
• 121-44-8 triethylamine 
• 67257-30-1 diethyl 2-oxo-3-butenylphosphonate 
• 112251-15-7 8a-methyl-6-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-3,7,8,8a-tetrahydronaphthalen-1(2H)-one 
• 109-87-5 Dimethoxymethane 
• 4242-00-6 (±)-4a,5-cis-(5-hydroxy-4a-methyl-4,4 a,5,6,7,8-hexahydronaphthalen-2(3H)-one) 
• 257941-62-1 (4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one 
• 20007-99-2 Wieland-Miescher ketone 
• 108-94-1 cyclohexanone 

Downstream Products

• 878-47-7 (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one 
• 257941-62-1 (4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one 
• 7499-70-9 4-(6-methyl-3-oxo-cyclohex-1-enyl)-butyric acid 
• 182370-29-2 (4aS,5R)-5-Hydroxy-4a-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-one 
• 878-47-7 (+/-)-5t-hydroxy-4a-methyl-(4ar)-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 4242-00-6 (±)-4a,5-cis-(5-hydroxy-4a-methyl-4,4 a,5,6,7,8-hexahydronaphthalen-2(3H)-one) 
• 112251-14-6 4a-methyl-5-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-4,4a,7,8-tetrahydronaphthalen-2(3H)-one 
• 112251-15-7 8a-methyl-6-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-3,7,8,8a-tetrahydronaphthalen-1(2H)-one 
• 112251-16-8 8a-methyl-3,8-bis-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-1,2,6,8a-tetrahydronaphthalen 
• 57234-61-4 γ-<3-Keto-6-methylcyclohexen-(1)-yl-(1)>-buttersaeuremethylester 
• 101328-30-7 methyl 4-(2,6-dimethyl-3-oxocyclohex-1-enyl)butyrate 
• 19133-70-1 8-hydroxy-5-methyl-1,2,3,4-tetrahydronaphtalene-1-one 
• 128242-25-1 4a-<6-(tert-butyldiphenylsiloxy)-1-hexen-1-yl>-8a-methyldecahydronaphthalene-1,6-dione 
• 6694-96-8 (1α,8aα)-(8a-Methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-1-naphthyl)-p-toluolsulfonat 

Relevant academic research and scientific papers

Promotion of one-pot Robinson annelation achieved by gradual pressure and temperature manipulation under supercritical conditions

The one-pot Robinson annelation from 2-methyl-cyclohexane-1,3-dione with 3-buten-2-one can be achieved in high yield (95%) and high selectivity (95%) by pressure and temperature manipulation using supercritical carbon dioxide in the presence of MgO catalyst, whose method could be applied for various ketones to synthesize fused polycyclic compounds.

An alternative chiral synthesis of Wieland-Miescher ketone mediated by (S)-2-(pyrrolidinylmethyl)pyrro-lidine: Remarkable effects of Br?nsted acid

The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by (S)-2-(pyrrolidinylmethyl)pyrrolidine to prepare Wieland-Miescher ketone was examined in detail. A remarkable inversion of enantioselectivity was observed when a Br?nsted acid was used as a co-catalyst. Development of the reaction to Robinson annulation was successfully achieved by the use of (S)-2-(pyrrolidinylmethyl)pyrrolidine as a Br?nsted base, followed by trifluoroacetic acid as a Br?nsted acid.

Recyclable L-proline organocatalyst for Wieland-Miescher ketone synthesis

Wieland-Miescher ketone 4 was synthesised using L-proline catalyst in the ionic liquid medium via non-selective conjugated addition reaction followed by an enantioselective intermolecular Aldol condensation reaction of triketone 3 intermediate. Short reaction time, recycling of the catalyst, good yield and selectivity are major outcomes of this proposed protocol. Indian Academy of Sciences.

Synthesis and use of 3,3′-bimorpholine derivatives in asymmetric Michael addition and intramolecular aldol reaction

The synthesis of 3,3′-bimorpholine and its N-alkyl derivatives is described. These new diamine derivatives were revealed to be efficient organocatalysts for the asymmetric Michael addition of aldehydes to nitroalkenes with excellent enantioselectivity (up to 90% ee). The potential of these organocatalysts was also demonstrated for the highly enantioselective intramolecular aldol reaction affording the Wieland-Miescher ketone with tremendous enantioselectivity (up to 95% ee). Georg Thieme Verlag Stuttgart.

N-Tosyl-(Sa)-binam-L-prolinamide as highly efficient bifunctional organocatalyst for the general enantioselective solvent-free aldol reaction

N-Tosyl-(Sa)-binam-L-prolinamide (5 mol%) and benzoic acid (1 mol%) were used as catalysts in the enantioselective direct aldol reaction between different ketones and aldehydes under solvent-free conditions in the presence or absence of water. Under these reaction conditions it was possible to reduce the amount of required ketone to two equivalents to give the corresponding aldol products with high yields, regio-, diastereo- and enantioselectivities. The aldol reaction between aldehydes or the intramolecular aldol reaction can be also performed with excellent results. Georg Thieme Verlag Stuttgart.

A synthetic approach to (±)-aristomakine

We describe the synthesis of trans-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol (2) in five steps from the Wieland-Miescher ketone 3 in 17% overall yield. The N-benzyl analogue (trans-11-Benzyl-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol) 15 was likewise prepared. Attempts thus far to fashion (±)-aristomakine (1) from 2, 15, or derivatives have not been successful.

One-pot synthesis of Wieland-Miescher ketone by enzymes

We first report that lipase from porcine pancreas catalyzed Robinson annulation in the organic media to synthesize the Wieland-Miescher ketone. The promiscuous catalytic activity of lipase in the Robinson reaction is due to an important role played by lipase activity in both the Michael addition and Aldol reaction.

Poly(Ethylene Glycol)-Supported Proline: A Versatile Catalyst for the Enantioselective Aldol and Iminoaldol Reactions

(2S,4R)-4-Hydroxyproline has been anchored to the monomethyl ether of poly(ethylene glycol), Mw 5000, by means of a succinate spacer to afford a soluble, polymer-supported catalyst (PEG-Pro) for enantioselective aldol and iminoaldol condensation reactions. This organic catalyst can be considered as a minimalistic version of a type I aldolase enzyme, with the polymer chain replacing the enzyme's peptide backbone, and the proline residue acting as the enzyme's active site. In the presence of PEG-Pro (0.25-0.35 mol equiv.), acetone reacted with enolizable and non-enolizable aldehydes and imines to afford β-ketols and β-aminoketones in good yield and high enantiomeric excess (ee), comparable to those obtained using non-supported proline derivatives as the catalysts. Extension of the PEG-Pro-promoted condensation to hydroxyacetone as the aldol donor opened an access to synthetically relevant anti-α,β-dihydroxyketones and syn-α-hydroxy-β-aminoketones, that were obtained in moderate to good yields, and good to high diastereo- and enantioselectivity. Exploiting its solubility properties, the PEG-Pro catalyst was easily recovered and recycled to promote all of the above-mentioned reactions, that occurred in slowly diminishing yields but virtually unchanged ee's.

Enantioselective synthesis of Wieland-Miescher ketone through bimorpholine-catalyzed organocatalytic aldol condensation

Novel bimorpholine-derived organocatalysts have been used for highly enantioselective intramolecular aldol reaction affording Wieland-Miescher ketone in high yield and enantioselectivity (up to 92% and 95%, respectively). Georg Thieme Verlag Stuttgart.

Enzymatic Baeyer-Villiger oxidation of bicyclic diketones

Cyclohexanone monooxygenase from Acinetobacter calcoaceticus was employed for the Baeyer-Villiger oxidation of racemic bicyclic diketones such as the Wieland-Miescher and the Hajos-Parrish diketones and of some of their derivatives. The corresponding lactones were produced in a highly regio-and enantioselective manner. The reactions were carried out using a crude enzyme preparation in aqueous buffer, at room temperature, and the recycling of the expensive coenzyme NADPH was conducted with a second ancillary enzymatic system. The enzymatic process was simple and easy to handle, thus providing a very practical tool to access enantiopure lactones.