53155-26-3

Usage

Chemical Structure

1,2-Benzisoxazole derivative with two methyl groups at the 3 and 5 positions

Explanation

The compound is derived from the benzisoxazole structure, which is a fused ring system consisting of a benzene ring and an isoxazole ring. The two methyl groups are attached to the 3 and 5 positions of the benzene ring.

Explanation

The compound is aromatic due to the presence of the benzene ring, which has a planar structure and exhibits resonance stabilization.

Explanation

The compound is used in the production of various pharmaceuticals and agrochemicals due to its unique structure and reactivity.

Explanation

The compound has been studied for its potential biological activities and is known for its ability to inhibit specific enzymes, which can be useful in the development of drugs targeting these enzymes.

Explanation

Due to its unique structure and reactivity, 1,2-Benzisoxazole, 3,5-dimethylis used as a building block in the synthesis of other organic compounds, allowing for the creation of a diverse range of molecules with various applications.

Explanation

The solubility of the compound in different solvents is not mentioned in the provided material. Solubility can be an important factor in determining the compound's suitability for specific applications.

Explanation

The stability of the compound under various conditions (e.g., temperature, pH, etc.) is not mentioned in the provided material. Stability can be a crucial factor in determining the compound's suitability for specific applications and storage conditions.

Aromatic Compound

Yes

Applications

Pharmaceutical and agrochemical production

Biological Activity

Inhibition of certain enzymes

Synthesis

Building block for other organic compounds

Upstream product

• 76288-12-5 1-(2-hydroxy-5-methyl-phenyl)-ethanon-(O-acetyl oxime ) 
• 33598-02-6 2'-hydroxy-5'-methylacetophenone imine 
• 25172-54-7 1-(2-hydroxy-5-methylphenyl)ethan-1-one oxime 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 

Downstream Products

• 76288-26-1 5-Methyl-3-((E)-styryl)-benzo[d]isoxazole 
• 76288-28-3 3-(4-methoxystyryl)-1,2-benzisoxazole 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 76288-34-1 7-Methyl-4-phenyl-3a,10b-dihydro-4H-2,10-dioxa-10a-aza-cyclopenta[a]fluorene-1,3-dione 
• 1394900-11-8 benzyl 1-(2-hydroxy-5-methylphenyl)-1-ethylcarbamate 

Relevant academic research and scientific papers

Method for preparing benzisoxazole in one pot based on 2-hydroxyacetophenone oxime and derivatives thereof

The invention relates to the technical field of medicinal chemistry and in particular discloses a method for preparing benzisoxazole in one pot based on 2-hydroxyacetophenone oxime and derivatives thereof. The preparation method is as follows: under microwave or oil bath heating conditions, in an organic solvent, one-pot inversion is carried out on 2-hydroxyacetophenone oxime and derivatives thereof to form benzisoxazole compounds by utilizing a fluorine-containing accelerator and alkali. The method for synthesizing benzisoxazole has the advantages that raw materials are rich in source and easy to get, synthetic steps are short, the operation is simple and convenient, the product yield is high, and the highest yield is 93%. A benzisoxazole structure exists in multiple drug molecules, so that the novel one-pot synthesis method disclosed by the invention has potential practical values.

A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine

A divergent and regioselective synthesis of either 3-substituted benzisoxazoles or 2-substituted benzoxazoles from readily accessible ortho-hydroxyaryl N-H ketimines is described. The reaction proceeds in two distinct pathways through a common N-Cl imine intermediate: (a) N-O bond formation to form benzisoxazole under anhydrous conditions and (b) NaOCl mediated Beckmann-type rearrangement to form benzoxazole, respectively. The reaction path also depends on the electronic nature of the aromatic ring, with the electron-rich aromatic rings favoring the rearrangement and the electron-deficient rings favoring the N-O bond formation. A Beckmann-type rearrangement mechanism via net [1,2]-aryl migration for the formation of 2-substituted benzoxazole is proposed.

Microwave induced synthesis of 3-substituted 1,2-benzisoxazole derivatives

A rapid, cost-effective and eco-friendly synthesis of 3-substituted 1,2-benzisoxazoles from o-hydroxy ketoximes in solvent free conditions using solid support under microwave irradiation has been achieved.

Synthesis of New Isoxazoles from Isoxazolines, Chalkones, Chalkone Dibromides, Epoxides and Acetylated Ketoximes and Their Conversion into Novel Heterocycles

A convenient and easy conversion of 2-isoxazolines (II) to isoxazoles (V) via N-bromosuccinimide bromination and subsequent dehydrobromination with bases is described.The isoxazoles have also been synthesized from chalkones (I), chalkone dibromides (III)