13304-52-4

Usage

Uses

Used in Fragrance and Flavor Industry:
2-methyl-3-phenyl-1H-inden-1-one is used as a key ingredient for creating fragrances and flavors due to its strong and pleasant odor. It is commonly incorporated into perfumes, soaps, and other personal care products to enhance their scent profiles.
Used in Pharmaceutical Industry:
2-methyl-3-phenyl-1H-inden-1-one is used as a building block in the synthesis of pharmaceuticals, contributing to the development of new drugs and medicinal compounds.
Used in Organic Chemistry:
2-methyl-3-phenyl-1H-inden-1-one is utilized in organic chemistry as a versatile intermediate for the synthesis of a variety of organic compounds, showcasing its importance in chemical research and development.
Safety Note:
It is crucial to handle 2-methyl-3-phenyl-1H-inden-1-one with care, as it can be harmful if ingested or inhaled and may cause skin and eye irritation. Proper safety measures should be taken during its use and storage to minimize potential health risks.

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 26260-02-6 2-iodobenzaldehyde 
• 98-88-4 benzoyl chloride 
• 7719-09-7 thionyl chloride 
• 17684-12-7 2-methyl-3,3-diphenyl-2-propenoic acid 
• 7664-93-9 sulfuric acid 
• 58473-62-4 ethyl 3-hydroxy-2-methyl-3,3-diphenylpropionate 
• 86119-84-8 phosphoric acid 
• 71-43-2 benzene 
• 4387-36-4 2-iodobenzonitrile 
• 19772-61-3 2-bromo-3-phenyl-1H-inden-1-one 
• 594-27-4 tetramethylstannane 
• 201230-82-2 carbon monoxide 
• 244205-40-1 (2-bromophenyl)boronic acid 

Downstream Products

• 110327-35-0 (2aR,7aR)-2-Benzoyl-7a-methyl-2,2a-diphenyl-1,2,2a,7a-tetrahydro-cyclobuta[a]inden-7-one 
• 110327-34-9 (5R,6aR,11bR)-5-Benzoyl-6a-methyl-11b-phenyl-5,6,6a,11b-tetrahydro-benzo[c]fluoren-7-one 
• 110327-34-9 (5S,6aR,11bR)-5-Benzoyl-6a-methyl-11b-phenyl-5,6,6a,11b-tetrahydro-benzo[c]fluoren-7-one 
• 110327-36-1 2-((6aR,11bR)-6a-Methyl-7-oxo-11b-phenyl-7,11b-dihydro-6aH-benzo[c]fluoren-5-yl)-propionic acid ethyl ester 
• 119610-47-8 C₂₇H₂₀O₃ 
• 119610-48-9 C₂₈H₂₂O₃ 
• 76836-54-9 3-methyl-4-phenyl-1H-isochromen-1-one 
• 87880-32-8 1-Methanesulfinylmethyl-2-methyl-3-phenyl-1H-inden-1-ol 
• 87880-38-4 3-Methyl-4-phenyl-naphthalen-1-ol 
• 85-52-9 2-Benzoylbenzoic acid 
• 65-85-0 benzoic acid 
• 33815-43-9 1-ethyl-2-methyl-3-phenyl-indan-1-ol 
• 857774-45-9 2-chloro-3-hydroxy-2-methyl-3-phenyl-indan-1-one 

Relevant academic research and scientific papers

Synthesis of Indenones Via Palladium-Catalyzed Carbonylation with Mo(CO)6 as a CO Surrogate

Transition-metal-catalyzed carbonylation of alkynes has emerged as a powerful engine for the synthesis of indenone compounds. Herein, we reported the development of an effective Pd-catalyzed ligand-free carbonylation of o-bromoaryl iodides with alkynes to afford indenone compounds. A broad range of functional groups on o-bromoaryl iodides and alkynes were tolerated in this protocol, giving carbonylation products. Furthermore, considering the factors of safety and operability, Mo(CO)6 was introduced into the reaction as a carbonyl source. Mechanistic investigations suggested that the reaction proceeded through sequential oxidative addition, alkyne insertion, carbonyl insertion, and reductive elimination steps to produce the observed carbonylation indenone products. Moreover, the indenones obtained with Mo(CO)6 as a CO surrogate can be functionalized to form synthetic useful derivatives via an environmentally friendly way.

Mechanochemical Solvent-Free Synthesis of Indenones from Aromatic Carboxylic Acids and Alkynes

The mechanochemical solvent-free synthesis of indenones from aromatic carboxylic acids and alkynes was achieved through triflic anhydride (Tf2O)-induced cyclization reaction. A variety of indenones including a bioactive PPARγagonist were obtained in up to 90% yield at room temperature. The present protocol has the advantages of mild reaction conditions, high reaction efficiency, and feasibility of scalable synthesis, providing a facile and sustainable route to diverse indenones.

Synthesis of indenones through rhodium(III)-catalyzed [3+2] annulation utilizing a recyclable carbazolyl leaving group

The rhodium(III)-catalyzed annulative coupling of 9-ben-zoylcarbazoles with internal alkynes proceeds efficiently through ortho CH and CN bond cleavages. This reaction provides direct access to variously substituted indanone derivatives. The carbazolyl leaving group can be readily recovered and reused for preparing the starting materials.

Efficient synthesis method of 2,3-indanone

The invention discloses an efficient synthesis method of 2,3-indanone. A heating reaction is carried out on o-substituted benzaldehyde and alkyne in an organic solvent under the catalysis of nickel and a phosphine ligand under the action of an alkali to obtain a 2,3-indanone product. O-substituted benzaldehyde and alkyne are used as raw materials, and the 2,3-indanone product is obtained in one step under the catalysis of metal nickel and the phosphine ligand under the action of the alkali, so the operation is simple and convenient, the regioselectivity is high, and the method is cheap and hasa good application prospect, and can be applied to efficient synthesis of natural products, medicines and materials.

Synthesis of Indenones via Palladium-Catalyzed Ligand-Free Carbonylation

A palladium-catalyzed ligand-free carbonylation reaction has been developed for the synthesis of indenones. Under CO atmosphere, this cascade reaction proceeded smoothly to provide the desired indenones in moderate to excellent yields with good functional-group compatibility. The mechanistic investigations suggested the in situ formation of palladium nanoparticles and this transformation was driven by a controlled reaction sequence of alkyne insertion followed by carbonylation and annulation to form the indenone framework. (Figure presented.).

An Approach to One-Pot Regioselective Synthesis of Indenones through Palladium-Catalyzed Annulation in Water

A one-pot synthesis of indenones is presented. The process involves palladium-catalyzed annulation of ortho-halobenzaldehydes with internal alkynes. Notably, it proceeded successfully in water as the sole, and green, solvent. Significantly, unlike in earlier reports, this protocol showed excellent regioselectivity with unsymmetrical alkylarylacetylenes. Further, the strategy was extended to a one-pot synthesis of a neolignan natural product.

Palladium-Catalyzed Acylations: One-Pot Synthesis of Indenones

An efficient, one-pot synthesis of substituted indenones was accomplished starting from simple o-iodoketones and aldehydes. [Pd]-catalyzed direct acylation of o-iodoketones with aldehydes was employed as the key step. Subsequent intramolecular aldol condensation afforded the indenones. Notably, a variety of indenones were achieved. Significantly, the natural product neolignan was accomplished in one pot.

Cobalt(III)-catalyzed annulation of esters and alkynes: A facile route to indenones

An efficient protocol for the synthesis of indenones has been developed via the annulation of benzoic esters and internal alkynes by exploiting the cobalt catalyst.

Palladium-catalyzed annulation of internal alkynes in aqueous medium

To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for carbo- and heteroannulation of internal alkynes with functionalized aryl halides in aqueous medium. A uniform reaction condition for these annulation reactions was also developed.

MeOTf-induced carboannulation of arylnitriles and aromatic alkynes: A new metal-free strategy to construct indenones

MeOTf-induced carboannulation of arylnitriles and aromatic alkynes for synthesis of indenones under metal-free conditions has been described. When ortho-substituted benzonitriles were used, indeno[1,2-c]isoquinolines were formed.