22582-67-8

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(1H-indol-3-yl)butan-1-one is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex molecular structures that can have therapeutic effects.
Used in Organic Chemistry:
In the field of organic chemistry, 1-(1H-indol-3-yl)butan-1-one is used as a building block for creating complex organic molecules, leveraging its indole ring and ketone group to form diverse chemical entities.
Used in Medicinal Chemistry and Drug Development:
1-(1H-indol-3-yl)butan-1-one is utilized as a structural component in the design and development of new drugs, taking advantage of its unique features to potentially enhance pharmacological properties and therapeutic applications.
Used in the Production of Tryptophan Metabolites and Indole Alkaloids:
1-(1H-indol-3-yl)butan-1-one serves as an essential intermediate in the synthesis of tryptophan metabolites and indole alkaloids, which are significant in various biological processes and have potential uses in medicine and other industries.

InChI:InChI=1/C12H13NO/c1-2-5-12(14)10-8-13-11-7-4-3-6-9(10)11/h3-4,6-8,13H,2,5H2,1H3

Upstream product

• 120-72-9 indole 
• 141-75-3 butyryl chloride 
• 106-31-0 butanoic acid anhydride 
• 109-74-0 propyl cyanide 

Downstream Products

• 405275-54-9 1-(4-chlorobenzyl)-3-(1-hydroxybutyl)-1H-indole 
• 558469-95-7 3-butyryl-1-(4-chlorobenzyl)-1H-indole 
• 111356-25-3 2-(3-propyl-1⁽²⁾H-pyrazol-4-yl)-aniline 

Relevant academic research and scientific papers

Insecticidal activity of indole derivatives against Plutella xylostella and selectivity to four non-target organisms

The diamondback moth Plutella xylostella (Linnaeus, 1758) (Lepidoptera: Plutellidae) is a destructive pest of brassica crops of economic importance that have resistance to a range of insecticides. Indole derivates can exert diverse biological activities, and different effects may be obtained from small differences in their molecular structures. Indole is the parent substance of a large number of synthetic and natural compounds, such as plant and animal hormones. In the present study, we evaluate the insecticidal activity of 20 new synthesized indole derivatives against P. xylostella, and the selectivity of these derivatives against non-target hymenopteran beneficial arthropods: the pollinator Apis mellifera (Linnaeus, 1758) (Hymenoptera: Apidae), and the predators Polybia scutellaris (White, 1841), Polybia sericea (Olivier, 1791) and Polybia rejecta (Fabricius, 1798) (Hymenoptera: Vespidae). Bioassays were performed in the laboratory to determine the lethal and sublethal effects of the compounds on P. xylostella and to examine their selectivity to non-target organisms by topical application and foliar contact. The treatments consisted of two synthesized derivatives (most and least toxic), the positive control (deltamethrin) and the negative control (solvent). The synthesized compound 4e [1-(1H-indol-3-yl)hexan-1-one] showed high toxicity (via topical application and ingestion) and decreased the leaf consumption by P. xylostella, displaying a higher efficiency than the pyrethroid deltamethrin, widely used to control this pest. In addition, the synthesized indole derivatives were selective to the pollinator A. mellifera and the predators P. scutellaris, P. sericea and P. rejecta, none of which were affected by deltamethrin. Our results highlight the promising potential of the synthesized indole derivatives for the generation of new chemical compounds for P. xylostella management.

Br?nsted acidic ionic liquid-promoted direct C3-acylation of: N -unsubstituted indoles with acid anhydrides under microwave irradiation

A green and efficient pathway for the synthesis of 3-acylindoles using a Br?nsted acidic ionic liquid as a catalyst has been developed for the first time. The C3-acylation of N-unsubstituted indoles with acid anhydrides affords the desired products in good to excellent yields with high regioselectivity under microwave irradiation. Moreover, the Br?nsted acidic ionic liquid can be recycled up to four times without significant loss of catalytic activity.

An efficient and green method for regio- and chemo-selective Friedel-Crafts acylations using a deep eutectic solvent ([CholineCl][ZnCl2]3)

[CholineCl][ZnCl2]3, a deep eutectic solvent between choline chloride and ZnCl2, has been used as a dual function catalyst and green solvent for the Friedel-Crafts acylation of aromatic compounds instead of using the moisture-sensitive Lewis acids and volatile organic solvents. The reactions are performed with high yields under microwave irradiation with short reaction times for the synthesis of ketones. Interestingly, indole derivatives are regioselectively acylated in the 3-position under mild conditions with high yields without NH protection. Three new ketone products are synthesized. [CholineCl][ZnCl2]3 is easily synthesized from choline chloride and zinc chloride at a low cost, with easy purification and environmentally benign compounds. [CholineCl][ZnCl2]3 can be reused up to five times without loss of catalytic activity, making it ideal in industrial processes.

A simple, effective, green method for the regioselective 3-acylation of unprotected indoles

A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized.

Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines

Abstract Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basification and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.

Palladium catalyzed addition of arylboronic acid or indole to nitriles: Synthesis of aryl ketones

Aryl ketones can be synthesized conveniently by a palladium catalyzed addition of arylboronic acid to nitriles in aqueous triflic acid. This catalytic system was extended to the addition of unprotected indoles to nitriles under a slightly modified condition to produce 3-acyl indoles in good yields.

THE FORMATION OF ACYLAMINO-DERIVATIVES OF INDOLES AND PYRROLES BY REACTIONS WITH NITRILIUM SALTS

N-Methylnitrilum fluoroborates are prepared rapidly by warming trimethyloxonium fluoroborate wiht a slight excess of the nitrile, subsquent addition of indoles and pyrroles at low temperatures (-50 deg C to -20 deg C) gives iminium salts (and hence ketones) in high yields.