A convenient preparation of indenone

Lacy, P. H.; Smith, Donald C.

doi:10.1039/j39710000041

Cited by 12 publications

(11 citation statements)

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“…Presumably, elimination of the acetoxy group occurred, followed by Michael reaction of the resulting indenone with methanol. The high reactivity of indenone to nucleophiles has been noted previously by Lacy and Smith (14).…”

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confidence: 65%

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An efficient synthesis of pterosin C and other pterosins

Ng¹,

McMorris²

1984

Can. J. Chem.

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A versatile synthetic route to pterosins, sesquiterpenoid indanones present in bracken, Pteridiumaquilinum, has been developed. The route is exemplified by the synthesis of (2S,3S)-pterosin C by Friedel–Crafts bisacylation of the methyl ether of 2-(2,6-dimethylphenyl)ethanol with methylmalonyl chloride. Demethylation of the resulting 1,3-indandione and reduction with zinc and acetic acid in the presence of acetic anhydride and sodium acetate afforded a mixture of racemic cis and trans isomers of pterosin C diacetate, which was hydrolysed to the corresponding pterosins. Separation and resolution via the S-(+)-α-phenylbutyric esters gave (2S,3S)-pterosin C and (2R,3R)-pterosin C. Other pterosins were prepared as racemates from the 1,3-indandione.

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confidence: 65%

“…Another unusual reaction employed in our synthesis was the selective reduction of the 1,3-indandione (4) to the diacetoxyindanone (5) by means of zinc and acetic acid in the presence of acetic anhydride and sodium acetate (14). The product contained the cis and trans isomers of 5 (64%, ratio of cis to trans, 1 :2) and the regioisomer 6 (16%).…”

mentioning

confidence: 99%

An efficient synthesis of pterosin C and other pterosins

Ng¹,

McMorris²

1984

Can. J. Chem.

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“…[64][65][66][67] This is because existing cobalt molecular catalysts perform very well in organic solvents when reducing CO 2 ; however, in aqueous environments, cobalt selectively promotes proton reduction and generates HER. [68][69][70] Thus, many heterogeneous loading methods have been developed over the past couple of years, to enable the catalyst's use in aqueous electrolytes, which are cost effective than organic solvents. [71][72][73] These loading methods typically involve either physically Adv.…”

Section: Cobalt-based Catalystsmentioning

confidence: 99%

Recent Trends, Benchmarking, and Challenges of Electrochemical Reduction of CO₂ by Molecular Catalysts

Elouarzaki

Kannan

Jose

et al. 2019

Advanced Energy Materials

168

102

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provides a promising alternative to hydrocarbon sources for petrochemical feedstock. Thanks to the electrochemical nature of the CO 2 conversion to fuels and chemicals, the electrical energy invested to convert CO 2 in the form of a chemical fuel can be stored and redistributed using established supply chains for future use. Additionally, the integration of renewable energy systems (green electricity) into the grid can potentially create a carbon neutral energy cycle, and when driven by solar energy, offers a completely renewable energy cycle or negative carbon technology. Converting CO 2 electrochemically into compounds with high energy densities, such as alcohols (methanol, ethanol), formates, and CO, represents a form of energy storage and is also adaptable to demand response or energy arbitrage technologies. [3][4][5][6][7] The recoverable energy density of the chemicals that can be converted from CO 2 is substantially higher than most battery technologies.Given CO 2 electroreduction's immense economic and environmental potential, it has been the subject of much research activity over the past decades. [8][9][10][11] One of the greatest challenges of reducing CO 2 in an electrochemical cell is overcoming the immense energy barrier required to do so; the single electron reduction of CO 2 to CO 2 −˙, a common step in many CO 2 reduction mechanisms, requires an applied potential of −1.97 V measured versus standard hydrogen electrode (SHE). To alleviate this problem, many catalytic cathodes have been developed to avoid this intermediate and to reroute the reduction mechanism through alternate pathways requiring much lower applied potentials (a necessity if CO 2 electroreduction is to be implemented at industrial scale). [12][13][14] However, despite the low potentials offered by catalytic electrodes, the cost of electrodes is not always viable when upscaled to industrial levels. [15,16] Therefore, recent research trends in electrocatalytic reduction of CO 2 have been shifting toward the development of molecular catalysts that can exist as either solutes in electrolytes or can be surface-confined on electrodes. [13,16] The tunable nature and electronic characteristics of molecular catalysts give access to a large variety of catalysts with high activity, selectivity, and durability, as well as their ability to be integrated into sophisticated nanoassemblies. [17][18][19] Thanks to the aforementioned proprieties, performing CO 2 reduction using molecularly defined compounds offer several advantages compared to classical solid-state counterparts. Molecular catalysts usually exhibit well-defined homogeneous and/or CO 2 reduction using molecular catalysts is a key area of study for achieving electrical-to-chemical energy storage and feedstock chemical synthesis. Compared to classical metallic solid-state catalysts, these molecular catalysts often result in high performance and selectivity, even under unfavorable aqueous environments. This review considers the recent state-of-the-art molecular catalysts for CO 2 electro...

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“…Syntheses of 3and 2-hydroxy-1-indanone. (±)-3-Hydroxy-1-indanone was prepared from 1,3-indandione in glacial acetic acid by treatment with zinc dust as described by Lacy et al (16). (+)-2-Hydroxy-1-indanone was synthesized by treating the TMS-enol ether of 1-indanone with m-chloroperoxybenzoic acid (19).…”

Section: Growth Of Pseudomonas Strains and Transformation Of Sub-mentioning

confidence: 99%

Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase

Resnick

Torok

Lee

et al. 1994

Appl Environ Microbiol

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The biotransformation of 1-indanone and 2-indanone to hydroxyindanones was examined with bacterial strains expressing naphthalene dioxygenase (NDO) and toluene dioxygenase (TDO) as well as with purified enzyme components. Pseudomonas sp. strain 9816/11 cells, expressing NDO, oxidized 1-indanone to a mixture of 3-hydroxy-1-indanone (91%) and 2-hydroxy-1-indanone (9%o). The (R)-3-hydroxy-1-indanone was formed in 62% enantiomeric excess (ee) (R:S, 81:19), while the 2-hydroxy-1-indanone was racemic. The same cells also formed 2-hydroxy-1-indanone from 2-indanone. Purified NDO components oxidized 1-indanone and 2-indanone to the same products produced by strain 9816/11. P. puta F39/D cells, expressing TDO, oxidized 2-indanone to (S)-2-hydroxy-1-indanone of 76% ee (R:S, 12:88) but did not oxidize 1-indanone eficiently. Purified TDO components also oxidized 2-indanone to (S)-2-hydroxy-1-indanone of 90%Yo ee (R:S, 5:95) and failed to oxidize 1-indanone. Oxidation of 1-and 2-indanone in the presence of [18O]oxygen indicated that the hydroxyindanones were formed by the incorporation of a single atom of molecular oxygen (monooxygenation) rather than by the dioxygenation of enol tautomers of the ketone substrates. As alternatives to chemical synthesis, these biotransformations represent direct routes to 3-hydroxy-1-indanone and 2-hydroxy-l-indanone as the major products from 1-indanone and 2-indanone, respectively.

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A convenient preparation of indenone

Cited by 12 publications

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An efficient synthesis of pterosin C and other pterosins

An efficient synthesis of pterosin C and other pterosins

Recent Trends, Benchmarking, and Challenges of Electrochemical Reduction of CO₂ by Molecular Catalysts

Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase

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A convenient preparation of indenone

Cited by 12 publications

References 0 publications

An efficient synthesis of pterosin C and other pterosins

An efficient synthesis of pterosin C and other pterosins

Recent Trends, Benchmarking, and Challenges of Electrochemical Reduction of CO2 by Molecular Catalysts

Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase

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Recent Trends, Benchmarking, and Challenges of Electrochemical Reduction of CO₂ by Molecular Catalysts