24644-78-8

Usage

Uses

Used in Organic Synthesis:
4-METHYL-1-INDANONE is used as a reagent for the synthesis of several organic compounds, including 3,6-dimethylcholanthrene, 3,6-dimethyl-7-methoxycholanthrene, and 3-methyl-7-methoxycholanthrene. It plays a crucial role in the formation of these compounds by participating in condensation reactions.
Used in Chemical Research:
In the field of chemical research, 4-METHYL-1-INDANONE is used as a starting material for the synthesis of various complex molecules. Its ability to undergo condensation reactions with other compounds makes it a valuable tool for researchers working on the development of new chemical entities.
Used in Pharmaceutical Industry:
4-METHYL-1-INDANONE may be utilized in the pharmaceutical industry for the synthesis of drugs and drug candidates. Its versatility in undergoing condensation reactions allows for the creation of a wide range of molecular structures with potential therapeutic applications.
Used in Material Science:
In material science, 4-METHYL-1-INDANONE can be employed in the development of novel materials with specific properties. Its ability to form various chemical structures through condensation reactions can contribute to the creation of materials with unique characteristics for different applications.

Upstream product

• 22084-89-5 3-(2-methylphenyl)propanoic acid 
• 107-94-8 chloropropionic acid 
• 108-88-3 toluene 
• 201230-82-2 carbon monoxide 
• 3989-15-9 trimethyl[(2-methylphenyl)ethynyl]silane 
• 7664-93-9 sulfuric acid 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 89-92-9 2-methylbenzyl bromide 
• 939-57-1 (E)-3-(2-methylphenyl)acrylic acid 
• 529-20-4 2-methylphenyl aldehyde 
• 67864-03-3 4-methyl-2,3-dihydro-1H-inden-1-ol 
• 85829-29-4 3-(2-methylphenyl)propionic acid chloride 
• 15115-60-3 4-bromo-2,3-dihydroinden-1-one 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 37102-74-2 3-methylphthalic acid 
• 824-22-6 2,3-dihydro-4-methyl-1H-indene 
• 133131-48-3 4-methyl-indan-1-one-(2,4-dinitro-phenylhydrazone) 
• 183545-51-9 2-(2-Carboxy-5-methylbenzyliden)-4-methylindan-1-on 
• 183545-56-4 2-(2-Carboxy-3-methylbenzyliden)-4-methylindan-1-on 
• 91445-80-6 2-bromo-2,3-dihydro-4-methylinden-1-one 
• 67864-03-3 4-methyl-2,3-dihydro-1H-inden-1-ol 
• 192987-46-5 4-[1-(1-hydroxy-4-methylindanyl)]-N-(triphenylmethyl)imidazole 
• 7372-92-1 7-methyl-1H-indene 
• 97232-09-2 7-Methyl-1H-indene-2-carbaldehyde 
• 24633-71-4 3-Methyl-2-cyanmethyl-benzoylchlorid 
• 882409-43-0 (-)-(R)-4-Methyl-1-indalol 

Relevant academic research and scientific papers

Using Data Science To Guide Aryl Bromide Substrate Scope Analysis in a Ni/Photoredox-Catalyzed Cross-Coupling with Acetals as Alcohol-Derived Radical Sources

Ni/photoredox catalysis has emerged as a powerful platform for C(sp2)–C(sp3) bond formation. While many of these methods typically employ aryl bromides as the C(sp2) coupling partner, a variety of aliphatic radical sources have been investigated. In principle, these reactions enable access to the same product scaffolds, but it can be hard to discern which method to employ because nonstandardized sets of aryl bromides are used in scope evaluation. Herein, we report a Ni/photoredox-catalyzed (deutero)methylation and alkylation of aryl halides where benzaldehyde di(alkyl) acetals serve as alcohol-derived radical sources. Reaction development, mechanistic studies, and late-stage derivatization of a biologically relevant aryl chloride, fenofibrate, are presented. Then, we describe the integration of data science techniques, including DFT featurization, dimensionality reduction, and hierarchical clustering, to delineate a diverse and succinct collection of aryl bromides that is representative of the chemical space of the substrate class. By superimposing scope examples from published Ni/photoredox methods on this same chemical space, we identify areas of sparse coverage and high versus low average yields, enabling comparisons between prior art and this new method. Additionally, we demonstrate that the systematically selected scope of aryl bromides can be used to quantify population-wide reactivity trends and reveal sources of possible functional group incompatibility with supervised machine learning.

A metal-free method for the facile synthesis of indanonesviathe intramolecular hydroacylation of 2-vinylbenzaldehyde

A facile method for the synthesis of indanones was developed under metal- and additive-free conditions, whereinl-proline served as an efficient and environmentally benign catalyst. Compared with previously synthesized indanones, synthesis by the transition-metal-catalyzed intramolecular hydroacylation of 2-vinylbenzaldehyde provided a more green synthetic pathway to indanone scaffolds with good to excellent yields. More importantly, it could be used to synthsize the anti-AD drug donepezil.

Copper-Catalyzed Enantioselective Domino Arylation/Semipinacol Rearrangement of Allylic Alcohols with Diaryliodonium Salts

A copper-catalyzed enantioselective arylative semipinacol rearrangement of allylic alcohols was developed. In the presence of a catalytic amount of an in situ generated chiral copper-bisoxazoline complex, reaction of allylic alcohols with diaryliodonium salts afforded spirocycloalkanones in high yields with high diastereo- and enantioselectivities. A two-point binding model engaging the carbon–carbon double bond and the proximal hydroxyl group was proposed to be responsible for the highly efficient chirality transfer.

Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones

Here we report a reagent-free rhodium-catalyzed ring-expansion reaction via C-C cleavage of cyclobutenones. A variety of poly-substituted cyclopentenones and 1-indanones can be synthesized from simple cyclobutenones and benzocyclobutenones. The reaction condition is near pH neutral without additional oxidants or reductants. The potential for developing a dynamic kinetic asymmetric transformation of this reaction has also been demonstrated. Further study supports the proposed pathway involving Rh-insertion into the cyclobutenone C-C bond, followed by β-hydrogen elimination, olefin insertion and reductive elimination.

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.

Compositions comprising an aryl pyrazole and a substituted imidazole, methods and uses thereof

This invention relates to compositions for combating parasites in animals, comprising 1-arylpyrazole compounds in combination with substituted imidazole compounds. This invention also provides for an improved methods for eradicating, controlling, and preventing parasite infestation in an animal comprising administering the compositions of the invention to an animal in need thereof.

Functionalization of styrenes by copper-catalyzed borylation/ ortho-cyanation and silver-catalyzed annulation processes

An efficient two-step method for the assembly of indanone derivatives starting from a simple vinyl arene has been developed. The sequence first involves addition of bis(pinacolato)diboron (B2pin2) and N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) to a broad range of styrenes by utilizing IMesCuCl as catalyst. This step simultaneously accomplishes hydroboration of the alkene and ortho cyanation of the benzene unit. The products thus obtained are further functionalized by a AgNO3/Selectfluor-mediated coupling of the BPin and cyano functionalities to annulate a new five-membered ring. This combined two-step sequence provides a versatile method for the site-selective derivatization of a broad range of vinyl arene substrates. A Cu and Ag sequence: The bis-functionalization of styrenes is accomplished through a copper-catalyzed process that enables hydroboration of the alkene and regioselective ortho cyanation of the arene. The resulting adducts are converted, by a radical cyclization process, into a cyclopentanone unit fused to the original aromatic ring. Together, these methods allow efficient cyclopentannulation of a broad range of styrene derivatives.

Non-conventional methodologies in the synthesis of 1-indanones

1-Indanones have been successfully prepared by means of three different non-conventional techniques, namely microwaves, high-intensity ultrasound and a Q-tube reactor. A library of differently substituted 1-indanones has been prepared via one-pot intramolecular Friedel-Crafts acylation and their efficiency and "greenness" have been compared.

Enantioselective organocatalytic iodination-initiated Wagner-Meerwein rearrangement

The present manuscript describes a high-yielding enantioselective semipinacol transposition, initiated by an electrophilic iodination event. The title transformation makes use of the anionic phase-transfer catalysis (PTC) paradigm for chirality induction. Thus, when combined appropriately, the insoluble cationic iodinating reagent S9 and the lipophilic phosphoric acid L9 act as an efficient source of chiral iodine that performs the semipinacol transposition of strained allylic alcohols A x to β-iodo spiroketones Bx in good yields and with high levels of diastereo- and enantio-induction. The product β-iodo spiroketones could be derivatized stereospecifically and without stereoerosion, giving rise to products inaccessible directly from a semipinacol rearrangement.

Sustainable flow oppenauer oxidation of secondary benzylic alcohols with a heterogeneous zirconia catalyst

A flow chemistry process for the Oppenauer oxidation of benzylic secondary alcohols using partially hydrated zirconium oxide and a simple carbonyl containing oxidant such as acetone, cyclohexanone, and neopentanal is reported. The heterogeneous oxidative system could be applied to a wide range of functionalized alcohol substrates, allowing clean and fast delivery of ketone products within a few minutes between 40 and 100 C.