51519-65-4

Usage

Uses

Used in Pharmaceutical Industry:
Tetralone serves as a building block in the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows it to be a key component in the development of new drugs and medicinal agents.
Used in Fragrance and Flavor Industry:
Tetralone is utilized in the production of fragrances and flavors, contributing to the creation of diverse scents and tastes in a variety of consumer products.
Used in Research and Development:
4,4a,6,7,8,8a-hexahydro-1,4-methanonaphthalen-5(1H)-one has been studied for its potential anti-inflammatory and anti-cancer properties, making it a subject of interest for researchers working on developing new treatments and therapies in the medical field.

InChI:InChI=1/C11H14O/c12-10-3-1-2-9-7-4-5-8(6-7)11(9)10/h4-5,7-9,11H,1-3,6H2

Upstream product

• 930-68-7 cyclohexenone 
• 542-92-7 cyclopenta-1,3-diene 
• 77-73-6 bi(cyclopentadiene) 
• 152668-34-3 Methyl cis-6-chloro-2-hexenoate 
• 51804-12-7 Methyl 6-chloro-2-hexynoate 

Downstream Products

• 1236179-64-8 2-oxapentacyclo[6.4.0.0(1,4).0(3,7).0(5,9)]dodecane 

Relevant academic research and scientific papers

Chiral Lewis acids derived from 1,8-Naphthalenediylbis(dichloroborane): Mechanistic aspects

Chiral Lewis acids derived from 1,8-Naphthalenediylbis(dichloroborane), a novel bidentate Lewis acid, have been found to be active catalysts for the asymmetric Diels-Alder reaction. Utilizing chiral ligands derived from amino acids, a range of enantioselectivities have been achieved with cyclopentadiene and various α,β-unsaturated aldehydes. Some mechanistic aspects of this novel asymmetric bidentate catalyst have been addressed.

Oxathiaborolium: A type of chiral Lewis acid catalyst and its application in catalytic and highly enantioselective Diels-Alder reactions

The first reported sulfur-stabilized borenium cations were synthesized through halide abstraction of a haloborane intermediate by halophilic reagents. Different from the well-known cationic oxazaborolidines, a sulfide instead of an amine was used to not only simplify the preparation of the catalysts but also increase Lewis acidity of the boron atom. The in situ generated borenium salts showed exceptional Lewis acidity and successfully catalyzed asymmetric Diels-Alder reactions of cyclopentadiene and dienophiles in excellent yields and enantioselectivities. The NMR studies of these oxathiaborolium structures were reported as well.

Rapid Access to Tricyclic Systems: Highly Endoselective Diels-Alder Reaction of Cycloalkenones with Cyclic Dienes under Microwave Irradiation

Cis fused ring systems are synthesized in good yields under microwave irradiation conditions in the presence of A1Cl3 as a catalyst within short time periods.

Oxathiaborolium-Catalyzed Enantioselective [4 + 2] Cycloaddition and Its Application in Lewis Acid Coordinated and Chiral Lewis Acid Catalyzed [4 + 2] Cycloaddition

The nascency of second-generation sulfur-stabilized borenium cations by halophilic Lewis acid SnCl4 leads to highly active chiral Lewis acids that are very effective catalysts for [4 + 2] cycloaddition. Oxathiaborolium pentachlorostannate (5-10 mol %) successfully catalyzed cycloaddition of various dienes and dienophiles to afford cycloadducts with excellent enantioselectivity (20 examples, up to 99% ee). This super Lewis acid also exhibited good enantioselectivity for the first Lewis acid coordinated and chiral Lewis acid catalyzed [4 + 2] cycloaddition to α,β-unsaturated mixed ester amide.

Conversion of Simple Cyclohexanones into Catechols

A novel I2-catalyzed direct conversion of cyclohexanones to substituted catechols under mild and simple conditions has been described. This novel transformation is remarkable with the multiple oxygenation and dehydrogenative aromatization processes enabled just by using DMSO as the solvent, oxidant, and oxygen source. This metal-free and simple system demonstrates a versatile protocol for the synthesis of highly valuable substituted catechols and therefore streamlines the synthesis and modification of biologically important molecules for drug discovery.

Silylium ion-catalyzed challenging Diels-Alder reactions: The danger of hidden proton catalysis with strong Lewis acids

The pronounced Lewis acidity of tricoordinate silicon cations brings about unusual reactivity in Lewis acid catalysis. The downside of catalysis with strong Lewis acids is, though, that these do have the potential to mediate the formation of protons by various mechanisms, and the thus released Bronsted acid might even outcompete the Lewis acid as the true catalyst. That is an often ignored point. One way of eliminating a hidden proton-catalyzed pathway is to add a proton scavenger. The low-temperature Diels-Alder reactions catalyzed by our ferrocene-stabilized silicon cation are such a case where the possibility of proton catalysis must be meticulously examined. Addition of the common hindered base 2,6-di-tert-butylpyridine resulted, however, in slow decomposition along with formation of the corresponding pyridinium ion. Quantitative deprotonation of the silicon cation was observed with more basic (Mes)3P to yield the phosphonium ion. A deuterium-labeling experiment verified that the proton is abstracted from the ferrocene backbone. A reasonable mechanism of the proton formation is proposed on the basis of quantum-chemical calculations. This is, admittedly, a particular case but suggests that the use of proton scavengers must be carefully scrutinized, as proton formation might be provoked rather than prevented. Proton-catalyzed Diels-Alder reactions are not well-documented in the literature, and a representative survey employing TfOH is included here. The outcome of these catalyses is compared with our silylium ion-catalyzed Diels-Alder reactions, thereby clearly corroborating that hidden Bronsted acid catalysis is not operating with our Lewis acid. Several simple-looking but challenging Diels-Alder reactions with exceptionally rare dienophile/enophile combinations are reported. Another indication is obtained from the chemoselectivity of the catalyses. The silylium ion-catalyzed Diels-Alder reaction is general with regard to the oxidation level of the α,β-unsaturated dienophile (carbonyl and carboxyl), whereas proton catalysis is limited to carbonyl compounds.

Experimental Diels-Alder reactivities of cycloalkenones and cyclic dienes explained through transition-state distortion energies

Quantum chemical calculations are used to investigate the experimentally measured reactivities of cyclic dienes and cycloalkenones in the Diels-Alder reaction. The interaction energies (red) are nearly constant; differences arise in changes in distortion energies of both dienophile (blue) and diene (green; see picture, Ea=activation energy; values in kcal mol-1). Copyright

Strained to the limit: When a cyclobutyl moiety becomes a thermodynamic sink in a protolytic ring-opening of photogenerated oxetanes

(Equation Presented). Strained polycyclic oxetanes generated photochemically from the Diels-Alder adducts of cyclic dienes and enones undergo deep skeletal rearrangements under protolytic ring-opening conditions offering expeditious access to chlorohydrins and other products of unique skeletal topology.

Chiral oxazaborolidine - Aluminum bromide complexes are unusually powerful and effective catalysts for enantioselective Diels - Alder reactions

Treatment of the chiral oxazaborolidine 1 with AlBr3 generates the 1:1 complex 3, which is an even more potent Lewis acid catalyst than protonated 1 (i.e., 2) for enantioselective Diels-Alder reactions. Only 4 mol % of catalyst 3 is required to achieve yields and enantiomeric purities of 90% over a broad range of achiral dienes and dienophiles. The ligand from which 3 is derived can be recovered easily and with high efficiency. The method is illustrated by 22 examples. Copyright

Studies in Lewis acid and LiClO4 (or Nafion-H) catalysed ionic Diels- Alder reactions of chiral and achiral olefinic acetals respectively

Chiral olefinic acetals derived from crotonaldehyde undergo ionic Diels- Alder reaction giving the corresponding cycloadducts in moderate to good diastereoselectivities. A variety of achiral olefinic acetals react with isoprene and cyclopentadiene to form the cycloadducts in good to excellent yields when catalysed by 4M LiClO4 in nitromethane or by Nafion-H in dichloromethane.