33878-96-5

Usage

Uses

Used in Traditional Medicine:
(S)-4,7A-DIMETHYL-2,3,7,7A-TETRAHYDRO-6H-INDENE-1,5-DIONE is used as a therapeutic agent for its anti-inflammatory and antioxidant properties, which contribute to its traditional medicinal applications.
Used in Food Industry:
In the food industry, (S)-4,7A-DIMETHYL-2,3,7,7A-TETRAHYDRO-6H-INDENE-1,5-DIONE is used as a flavoring agent to enhance the taste and aroma of various products.
Used in Fragrance Industry:
(S)-4,7A-DIMETHYL-2,3,7,7A-TETRAHYDRO-6H-INDENE-1,5-DIONE is used as a component in the production of fragrances, capitalizing on its unique scent properties.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (S)-4,7A-DIMETHYL-2,3,7,7A-TETRAHYDRO-6H-INDENE-1,5-DIONE is used as a subject of research for its potential medical applications, given its ability to interact with biological systems and exhibit pharmacological effects.

InChI:InChI=1/C11H14O2/c1-7-8-3-4-10(13)11(8,2)6-5-9(7)12/h3-6H2,1-2H3/t11-/m0/s1

Upstream product

• 765-69-5 2-Methylcyclopentane-1,3-dione 
• 1629-58-9 4-penten-3-one 
• 34927-37-2 2-(3-oxopentyl)-2-methylcyclopentane-1,3-diones 

Downstream Products

• 678160-22-0 1-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-1-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-ethanol 
• 678159-96-1 tert-Butyl-{(2S,3R,3aR,5R,6aR)-5-methoxy-3-[1-((1R,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-vinyl]-hexahydro-furo[2,3-b]furan-2-ylmethoxy}-diphenyl-silane 
• 678160-11-7 [(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-methanone 
• 678159-99-4 (1S,7aS)-1-(tert-Butyl-diphenyl-silanyloxy)-4,7a-dimethyl-1,2,3,6,7,7a-hexahydro-inden-5-one 
• 678160-00-4 (1S,7aS)-1-(tert-Butyl-diphenyl-silanyloxy)-4,4,7a-trimethyl-1,2,4,6,7,7a-hexahydro-inden-5-one 
• 678160-02-6 tert-butyl-diphenyl-(4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-1-yloxy)-silane 

Relevant academic research and scientific papers

Total synthesis of (+)-cyclomyltaylan-5α-ol isolated from the Taiwanese Liverwort Reboulia hemisphaerica

The novel tetracyclic sesquiterpenoid (+)-cyclomyltaylan-5α-ol 1 has been synthesized starting from (S)-(+)-Hajos-Wiechert ketone analogue 3 via Sml2-promoted reductive cyclization as a key step. Thus, the absolute configuration has been established to be 2R,3R,4R,5S,6R,7R (cyclomyltaylane numbering) as depicted in structure 1.

Total synthesis of (-)-austalide B. A generic solution to elaboration of the Pyran/p-Cresol/Butenolide triad

The toxic meroterpenoid (-)-austalide B has been prepared in its natural form by chemical modification of the readily available optically active enedione 11. Following stereocontrolled Robinson annulation to give 13 and fully regiocontrolled gem-dimethyla

The first enantioselective total synthesis of cyclomyltaylane-5α-ol and determination of its absolute stereochemistry

The tetracyclic sesquiterpenoid (+)-cyclomyltaylan-5α-ol 1 has been synthesized starting from (S)-(+)-Hajos-Wiechert ketone analogue 10 via stereoselective Claisen rearrangement followed by SmI2-promoted reductive cyclisation. Thus, the absolut

Desymmetrisation of: Meso -diones promoted by a highly recyclable polymer-supported chiral phosphoric acid catalyst

A polystyrene-supported BINOL-derived chiral phosphoric acid has been applied to the desymmetrisation of meso-diones to produce enantioenriched cyclohexenones. The catalytic resin has proven highly active and robust, giving rise to Hajos-Parrish or Wieland-Miescher type products in good yields and enantioselectivities, while allowing for extended recycling.

A Highly Active Polymer-Supported Catalyst for Asymmetric Robinson Annulations in Continuous Flow

The preparation through Robinson annulation of enantiopure building blocks with both academic and industrial relevance, such as the Wieland-Miescher and Hajos-Parrish ketones, has suffered from important drawbacks, such as the need for high catalyst loading or extremely long reaction times. Here we report a heterogenized organocatalyst based on Luo's diamine for fast and broad-scope enantioselective Robinson annulation reactions. The polystyrene-supported diamine 19a enables the high-yield, highly enantioselective preparation of a wide range of chiral bicyclic enones under mild conditions, with reaction times as short as 60 min (batch) or residence times of 10 min (flow). In contrast with its homogeneous counterpart 19b, the catalytic resin 19a experiences a notable increase in catalytic activity with temperature in 2-MeTHF (a 10-fold decrease in reaction times without erosion in enantioselectivity is observed from room temperature to 55 °C). The scope of the transformation in batch mode has been illustrated with 14 examples, including examples only reported in poorly enantioenriched (22n) or in racemic form (22k). Enantiopure 22k has been used as the starting material for a straightforward formal synthesis of the antibiotic and antifeedant sesquiterpene (-)-isovelleral (24). The heterogenized catalyst 19a admits extended recycling (10 cycles) and has been used to develop the first asymmetric Robinson annulations in continuous flow. The potential of the flow process is illustrated by the large-scale preparation of the Wieland-Miescher ketone (65 mmol in 24 h of operation, TON of 117) and by a sequential flow experiment leading to a library of eight enantioenriched diketone compounds.

Total Synthesis of (-)-Chromodorolide B

The first total synthesis of a chromodorolide diterpenoid is described. The synthesis features a bimolecular radical addition/cyclization/fragmentation cascade that unites butenolide and trans-hydrindane fragments while fashioning two C-C bonds and stereoselectively forming three of the ten contiguous stereocenters of chromodorolide B.

Evaluating β-amino acids as enantioselective organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert reaction

A systematic study of the effect of substitution within the β-amino acid framework indicates that both β2- and β3- amino acids catalyse the Hajos-Parrish-Eder-Sauer-Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained β-amino acid (1R,2S)-cispentacin, which catalyses the Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity to l-proline. The Royal Society of Chemistry.

Recyclable asymmetric cyclization in ionic liquid catalyzed by an amino acid, leading to a Wieland-Miescher ketone analogue

A procedure for recyclable asymmetric cyclization leading to optically active Wieland-Miescher ketone analogue has been developed employing D-phenylalanine and D-CSA in [hmim]PF6 and dimethylimidazolidinone in 81% chemical yield and 74% enantio

Norrisolide: Total synthesis and related studies

A stereoselective synthesis of (+)-norrisolide is presented. This natural product belongs to a family of marine spongiane diterpenes the structure of which is characterized by a fused γ-lactone-γ-lactol ring system attached to a bicyclic hydrophobic core.

Formal total synthesis of (+)-wortmannin using catalytic asymmetric intramolecular aldol condensation reaction

A catalytic process for the synthesis of optically active C4-substituted tetrahydroindandiones using an asymmetric intramolecular aldol condensation reaction was developed. When 30 mol% of phenylalanine and 50 mol% of pyridinium p-toluenesulfonate were us