16643-55-3

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Dimethyl-3,4-diphenylcyclopent-2-en-1-one is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drug molecules. Its unique structure allows it to be a key component in the creation of various medicinal compounds.
Used as a Flavoring Agent:
In the food and beverage industry, 2,5-Dimethyl-3,4-diphenylcyclopent-2-en-1-one is used as a flavoring agent to impart specific taste profiles to products. Its chemical properties enable it to enhance or create unique flavors in a variety of food items.
Used in Organic Synthesis:
2,5-Dimethyl-3,4-diphenylcyclopent-2-en-1-one is utilized as a building block in the synthesis of other organic compounds. Its versatile structure makes it a valuable component in the creation of a wide range of organic molecules for various applications across different industries.

Upstream product

• 13360-84-4 2,5-dimethyl-3,4-diphenylcyclopenta-2,4-dione dimer 
• 446873-32-1 7-hydroxy-1.4-dimethyl-2.3.5-triphenyl-norbornene-⁽²⁾ 
• 75391-07-0 2-methyl-1-phenylpent-1-en-3-one 
• 100-52-7 benzaldehyde 
• 56406-94-1 1,7-Dimethyl-8,9-diphenyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-4,10-dione 
• 42124-16-3 2,4?dimethyl?1,5?diphenylpenta?1,4?dien?3?one 
• 96-22-0 pentan-3-one 
• 42124-16-3 1,5-diphenyl-2,4-dimethyl-1,4-pentadien-3-one 
• 5141-38-8 2,5-Dimethyl-3,4-diphenyl-cyclopent-2-en-1,4-diol 
• 5423-06-3 4-hydroxy-2,5-dimethyl-3,4-diphenylcyclopent-2-enone 
• 134-81-6 benzil 
• 68226-09-5 r-2,cis-6-diphenyl-trans-3,5-dimethyl-4-oxanone 

Downstream Products

• 67209-33-0 2,5-dimethyl-1,3,4-triphenyl-cyclopentadiene 
• 1352282-68-8 C₂₀H₂₀ 
• 4916-75-0 1,2,3-trimethyl-4,5-diphenyl-cyclopentadiene 
• 4916-74-9 (3,5-dimethylcyclopenta-2,5-diene-1,2-diyl)dibenzene 
• 65007-15-0 1,4-dimethyl-2,3-diphenyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione 
• 5141-37-7 2,5-Dimethyl-3,4-diphenyl-cyclopent-2-en-1-ol 

Relevant academic research and scientific papers

Interrupting Nazarov Reaction with Different Trapping Modality: Utilizing Potassium Alkynyltrifluoroborate as a σ-Nucleophile

The putative oxyallyl cation intermediate generated following Nazarov cyclization of dienone has been successfully intercepted with potassium alkynyltrifluoroborates which act as σ-nucleophiles in the presence of BF3·Et2O. This new t

Optimization of nazarov cyclization of 2,4-dimethyl-1,5-diphenylpenta-1,4-dien-3-one in deep eutectic solvents by a design of experiments approach

The unprecedentedNazarov cyclization of amodel divinyl ketone using phosphonium-based Deep Eutectic Solvents as sustainable non-innocent reactionmedia isdescribed. Atwo-level full factorial Design ofExperimentswas conductedfor elucidating the effect of the components of the eutecticmixture and optimizing the reaction conditions in terms of temperature, time, and substrate concentration. In the presence of the Deep Eutectic Solvent (DES) triphenylmethylphosphonium bromide/ethylene glycol, it was possible to convert more than 80% of the 2,4-dimethyl-1,5-diphenylpenta-1,4-dien-3-one, with a specific conversion, into the cyclopentenone Nazarov derivative of 62% (16 h, 60 °C). For the reactions conducted in the DES triphenylmethylphosphonium bromide/acetic acid, quantitative conversions were obtained with percentages of the Nazarov product above 95% even at 25 °C. Surface Responding Analysis of the optimized data furnished a useful tool to determine the best operating conditions leading to quantitative conversion of the starting material, with complete suppression of undesired side-reactions, high yields and selectivity. After optimization, it was possible to convert more than 90% of the model substrate into the desired cyclopentenone with cis percentages up to 77%. Experimental validation of the implemented model confirmed the robustness and the suitability of the procedure, leading to possible further extension to this specific combination of experimental designs to other substrates or even to other synthetic processes of industrial interest.

Reagent-free Nazarov cyclisations

A new protocol for Nazarov cyclisation is described that involves simple heating of dienones in the absence of any external Lewis acid. The Royal Society of Chemistry 2005.

Natural deep eutectic solvents as an efficient and reusable active system for the Nazarov cyclization

Natural deep eutectic solvents have emerged as alternative non-toxic, non-aqueous solvents for an increasing number of synthetic transformations. Remarkably, in some cases one (or more) components of the NaDES plays an active role in the reaction mechanism and directly participates as either a catalyst or a reagent in the reaction. In this paper, we tested several NaDESs in which one of the components is a carboxylic acid as a medium to perform the Nazarov cyclization of divinyl ketones to obtain cyclopentenones, a widespread motif in natural compounds. The reaction conditions were optimized and the scope was investigated on C-, O- A nd N-derived compounds. To assess the full sustainability of the proposed approach, the recyclability and scalability of the process were investigated, thus proving that multi-gram preparations are possible with complete recycling of the medium.

Pd(II)-Catalyzed Enantioselective Desymmetrization of Polycyclic Cyclohexenediones: Conjugate Addition versus Oxidative Heck

Pd(II)-catalyzed desymmetrization of polycyclic cyclohexenediones has been achieved with high enantio- and diastereoselectivities. Up to five contiguous stereocenters are desymmetrized, while simultaneously, an additional stereocenter is created by the enantioselective conjugate addition. Surprisingly, the conjugate addition products dominate even under typical oxidative Heck conditions, and these observations may provide some insight into the competition between the two related reactions.

Synthesis of oxathiane and morpholine from acyclic precursors: A modified Mitsunobu reaction

Synthesis of a set of isomeric 2,4,6-triarylmorpholines and 2,6-diaryloxathianes from the corresponding 1,5-diols has been described. The method provides an efficient route to six-membered heterocycles from acyclic diols and is found to be better than Mitsunobu procedure in yield and waste management. In a related study, the ring contraction of pyranone to two isomeric cyclopentenone derivatives through Nazarov reaction has been noticed.

Polymer-mediated reactions. A Nazarov-like cyclization

The polymer PEDOT+ mediates a Nazarov-like cyclization of dienones, in an heterogeneous system and in hydrocarbon solvents. The polymer-mediated reactions show clear differences in product formation when compared to the same reaction with tosic acid, or when compared to reports in the literature. Comparable or improved yields are observed, as well as the ability to give a -Nazarov product in cases where treatment with acid fails to give cyclization, or leads to an undesirable rearrangement. In addition, the ability to recycle the polymer makes this a potentially useful protocol for an important organic chemical reaction. Georg Thieme Verlag Stuttgart · New York.

Synthesis of multisubstituted cyclopentadienes from cyclopentenones prepared via catalytic double aldol condensation and nazarov reaction sequence

The rhenium-catalyzed synthesis of cyclopentenone derivatives via double aldol condensation and successive Nazarov reaction is described. The cyclopentenones were converted to the corresponding cyclopentadienes using organolithium reagents. Cyclopentadien

Tandem Nazarov cyclization-halovinylation of divinyl ketones under Vilsmeier conditions: Synthesis of highly substituted cyclopentadienes

A new Vilsmeier reagent-mediated Nazarov cyclization-halovinylation reaction of divinyl ketones was developed to provide a straightforward method for the synthesis of highly substituted cyclopentadienes with the advantages of simplicity of execution, readily available substrates, cheap reagents, and broad range of potential products and applications.

One-pot synthesis of the derivatives of 2-cyclopent-2-en-1-one by SOCl 2/EtOH

A simple and efficient method for the synthesis of derivatives of cyclopent-2-en-1-one is presented. Aromatic aldehydes reacted with aliphatic ketones in the presence of thionyl chloride in anhydrous ethanol to give seven derivatives of 2-cyclopenten-1-one in one step with reasonable yields. The structures of the products were established.