82359-81-7

Usage

Uses

Used in Organic Synthesis:
2,3-dihydro-3-methylene-2-benzyl-1H-isoindolone is used as a versatile building block in organic synthesis for the creation of various organic compounds and materials. Its unique structure and reactivity make it a valuable intermediate in the synthesis process, facilitating the development of new chemical entities with potential applications across different industries.
Used in Pharmaceutical and Medicinal Applications:
In the pharmaceutical and medicinal industry, 2,3-dihydro-3-methylene-2-benzyl-1H-isoindolone is utilized as a key intermediate for the development of new drugs. Its unique chemical properties allow for the exploration of its potential therapeutic effects, making it a promising candidate for further research and development in drug discovery.
While the provided materials do not specify particular applications within different industries, the general uses outlined above are based on the compound's properties and potential in organic synthesis and pharmaceutical development. Further research and development would be necessary to identify specific applications and industries where 2,3-dihydro-3-methylene-2-benzyl-1H-isoindolone could be effectively utilized.

Upstream product

• 3598-68-3 3-(nitromethyl)-isobenzofuran-1-(3H)-one 
• 100-46-9 benzylamine 
• 19339-65-2 3-Chloro-3-methyl-1(3H)-isobenzofuranone 
• 103-49-1 dibenzylamine 
• 201230-82-2 carbon monoxide 
• 2142-69-0 2-bromophenyl methyl ketone 
• 1202784-78-8 N-[1-(2-chlorophenyl)ethylidene]benzylamine 
• 38846-64-9 2-ethynylbenzaldehyde 
• 33578-00-6 (2-ethynyl)benzoic acid 
• 13380-32-0 2-benzylisoindolin-1-one 
• 68-12-2 N,N-dimethyl-formamide 
• 88-67-5 2-Iodobenzoic acid 
• 293744-64-6 N-benzyl-2-[2-(trimethylsilyl)ethynyl]benzamide 
• 97049-78-0 2,3-dihydro-3(nitromethyl)-2-phenylmethyl-1H-isoindol-1-one 

Downstream Products

• 1726-16-5 1,3-dihydro-3-methyl-2-phenylmethyl-2H-isoindole-1-one 
• 104563-12-4 2-Benzyl-3-(4-hydroxy-phenyl)-3-methyl-2,3-dihydro-isoindol-1-one 
• 82359-83-9 aristolactam 
• 128413-27-4 2-Benzyl-3-[2-[(E)-hydroxyimino]-2-(4-trifluoromethyl-phenyl)-eth-(E)-ylidene]-2,3-dihydro-isoindol-1-one 
• 128413-24-1 2-(phenylmethyl)-3'-<4-(trifluoromethyl)phenyl>spiro<1H-isoindole-1,5'(4'H)-isoxazol>-3(2H)-one 
• 128413-28-5 2-Benzyl-3-[2-(4-chloro-phenyl)-2-[(E)-hydroxyimino]-eth-(E)-ylidene]-2,3-dihydro-isoindol-1-one 
• 128413-25-2 3'-(4-chlorophenyl)-2-(phenylmethyl)spiro<1H-isoindole-1,5'(4'H)-isoxazol>-3(2H)-one 

Relevant academic research and scientific papers

Metal-Free Selective and Diverse Synthesis of Three Distinct Sets of Isoindolinones from 2-Alkynylbenzoic Acids and Amines

The metal-free selective and diverse synthesis of three distinct sets of isoindolinones from 2-alkynylbenzoic acids and amines has been achieved in a reaction-condition-controlled manner. This method exhibits valuable advantageous features such as available starting materials, broad substrate scope, excellent selectivity, good to high yields, good functional group tolerance, simple operation, high bond-forming efficiency, and step economy, thus providing a convenient and efficient access to a variety of heterocyclic compounds incorporating the bioactive isoindolinone motif.

Reduction of Benzolactams to Isoindoles via an Alkoxide-Catalyzed Hydrosilylation

An alkoxide-catalyzed reduction of benzolactams to isoindoles with silanes was realized. With t-BuOK as the catalyst and Ph2SiH2 as the reductant, a series of benzolactams containing different functional groups were reduced to the co

Reactant cum solvent water: Generation of transient λ3-hypervalent iodine, its reactivity, mechanism and broad application

An outstanding amidation/imidation process is demonstrated under metal-free benign reaction conditions by grafting terminal alkynes with varied amines and reactant cum solvent water. We explored diverse substrate scope in the nonconventional approach for synthesis of several classes of valuable compounds bearing amide linkages such as N-tosyl, N-aminotosyl, N-oxobenzyl, N-alkylated sugar-based secondary and tertiary chiral amides and also exploiting it for synthesis of valuable cyclic imides through simultaneous activation of triple bond and sp2C-H of aldehyde. The in situ-generated powerful reagent PhI(OH)2 enables selective cleavage and functionalization of terminal C-C triple bonds through simultaneous construction of C-N and C=O bonds. A measurable breakthrough in time-resolved ATR-MIR spectroscopy of the ongoing λ3-hypervalent iodine controlled reaction revealed formation of the unknown intermediates. The ATR-MIR technology is used for identifying infrared (IR) spectra of the individual intermediate/component present in the reaction mixture, which contains several compounds. The structures of the intermediates and their IR spectra were determined by DFT study. This unprecedented combination of experimental results and theoretical prediction provided useful information regarding the reaction insights such as the cleavage of triple bond, amination and amidation in the complex reaction process involving λ3-hypervalent iodine-bearing labile intermediates to the desired amide. The NMR and labelling (2H and 18O) studies supported the DFT-IR predicted reaction pathway.

Synthesis of 3-methyleneisoindolin-1-ones via palladium-catalyzed C-Cl bond cleavage and cyclocarbonylation of ortho-chloro ketimines

PdCl2(PCy3)2-catalyzed cyclocarbonylative coupling of ortho-chloro arylketimines with CO has been investigated to develop an efficient method for the synthesis of isoindolin-1-ones. The developed synthetic method has the a

Product selectivity control in the heteroannulation of o-(1-Alkynyl)benzamides

The selective synthesis of (Z)- or (E)-3-aryl/vinyl/alkylidene-isoindolones, and 2-benzopyran derivatives from o-(1-alkynyl)benzamides by means of a suitable choice of bases or silver catalysis is described.

Palladium-catalysed convenient synthesis of 3-methyleneisoindolin-1-ones

2′-Bromoacetophenone reacts with an array of aliphatic primary amines under carbon monoxide pressure in the presence of a catalytic amount of a palladium catalyst to afford 3-methyleneisoindolin-1-ones in moderate yields.

Palladium-catalysed heteroannulation with terminal alkynes: A highly regio- and stereoselective synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1- ones

A highly regio- and stereoselective method for the synthesis of (Z)-3- aryl(alkyl)idene isoindolin-1-ones through palladium-copper catalysis is described. 2-Iodobenzamide 1 and its substituted derivatives 2-10 were reacted with terminal alkynes 11-19 in the presence of (PPh3)2PdCl2, CuI, and Et3N in DMF mostly at 80°C for 16 h to yield the 2-alkynyl substituted benzamides 20-38, 40-45, 77 which could then be cyclised with NaOEt in EtOH to the 3-aryl(alkyl)idene isoindolin-1-ones 46-49, 51, 53-55, 57, 59-71, 73 and 75. In certain cases, the isoindolin-1-ones 50, 52, 56 and 58 could be directly obtained by the palladium-catalysed reactions. (C) 2000 Elsevier Science Ltd.

A highly regio and stereoselective synthesis of (Z)-3- aryl(alkyl)idene isoindolin-1-ones via palladium catalyzed annulation of terminal alkynes

o-Iodobenzamide or its N-substituted derivatives 4-10 and terminal alkynes 11-17 reacted in DMF in the presence of bis(triphenylphosphine)palladium(II)chloride, cuprous iodide and triethylamine leading to (Z)-3- arylidene isoindolin-1-ones (22, 24, 27 and 28) or o-alkynyl N-substituted benzamides (I). The latter could be cyclised with sodium in ethanol in a completely regio and stereoselective manner to (Z)-3-aryl(alkyl)idene isoindolin-1-ones 18-35.

Preparation of 3-Hydroxyindolin-1-ones and o-Acylbenzamides. A Study of Ring-Chain Tautomerism

3-Hydroxyisoindolinones (ring form) as well as their chain tautomers, o-acylbenzamides, were prepared from the reactions of 3-benzalphthalide 1, 3-halophthalides 3, and o-acylbenzoic acids 6 or their esters 7 with amines 2, and those of phthalimides 4 wit