5541-89-9

Usage

Uses

Used in Organic Synthesis:
4-(1H-INDOL-3-YL)BUTAN-2-ONE is used as a key intermediate in organic synthesis for the preparation of various chemical compounds. Its unique structure and reactivity make it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
4-(1H-INDOL-3-YL)BUTAN-2-ONE is used as a building block for the development of pharmaceuticals. Its presence in the molecular structure of various drugs contributes to their therapeutic effects. 4-(1H-INDOL-3-YL)BUTAN-2-ONE's versatility in chemical reactions allows for the creation of new pharmaceutical agents with improved efficacy and reduced side effects.
Used in Natural Product Synthesis:
4-(1H-INDOL-3-YL)BUTAN-2-ONE is employed in the synthesis of natural products, which are derived from plants, animals, and microorganisms. These natural products often possess unique biological activities and are used as lead compounds for drug discovery. 4-(1H-INDOL-3-YL)BUTAN-2-ONE's ability to mimic the structural features of natural products makes it an essential component in their synthesis.
Used in Bioactive Molecule Synthesis:
4-(1H-INDOL-3-YL)BUTAN-2-ONE is used as a precursor in the synthesis of bioactive molecules, which exhibit various biological activities such as antimicrobial, antiviral, anti-inflammatory, and anticancer properties. 4-(1H-INDOL-3-YL)BUTAN-2-ONE's potential biologically active properties make it a promising candidate for the development of novel therapeutic agents.

InChI:InChI=1/C12H13NO/c1-9(14)6-7-10-8-13-12-5-3-2-4-11(10)12/h2-5,8,13H,6-7H2,1H3

Upstream product

• 120-72-9 indole 
• 78-94-4 methyl vinyl ketone 
• 100956-30-7 ethyl 2-((1H-indol-3-yl)methyl)-3-oxobutanoate 
• 106462-95-7 (E)-4-(1-methoxy-1H-indol-3-yl)but-3-en-2-one 
• 860360-21-0 2-(1H-indol-3-ylmethyl)-3-oxo-butyric acid 
• 922-67-8 propynoic acid methyl ester 
• 31951-75-4 (E)-4-(1H-indol-3-yl)but-3-en-2-one 
• 67282-55-7 1-methoxy-1H-indole-3-carbaldehyde 
• 603-76-9 1-methylindole 
• 764-01-2 methyl propargyl alcohol 
• 2028-63-9 but-3-yn-2-ol 
• 1380392-38-0 C₁₀H₁₁NO 
• 98-95-3 nitrobenzene 
• 31951-75-4 4-(1H-indol-3-yl)-but-3-en-2-one 

Downstream Products

• 14105-23-8 4-(3-indolyl)butan-2-one oxime 
• 666177-62-4 4-(3-indolyl)butan-2-one oxime 
• 666177-55-5 C₁₉H₁₂ClF₅N₂O 
• 666177-56-6 3',4'-dihydro-2-hydroxy-5'-methyl-1-pentafluorobenzoylspiro[indoline-3',2-[2H]pyrrole] 
• 14105-23-8 4-(1H-indol-3-yl)butan-2-one oxime 
• 15467-30-8 3-(1H-indol-3-yl)-1-methyl-propylamine 
• 18992-67-1 1,2-dimethyl-9H-carbazole 

Relevant academic research and scientific papers

Clay (Montmorillonite K10) catalysis of the Michael addition of α,β-unsaturated carbonyl compounds to indoles: The beneficial role of alcohols

The Michael addition of methylvinylketone to indole can be performed under smooth conditions by running the reaction in the presence of an acidic clay catalyst (K10 Montmorillonite) and an aliphatic alcohol such as ethanol or 2-propanol. Presence of an alcohol along with a polar solvent (nitromethane) in the reaction medium considerably improves the reaction.

Boron-Catalyzed Dehydrative Friedel-Crafts Alkylation of Arenes Using β-Hydroxyl Ketone as MVK Precursor

Boron-catalyzed environmentally benign dehydrative Friedel-Crafts alkylation of indole/pyrrole and aniline derivatives with β-hydroxyl ketones has been developed for the first time. This method provides an efficient and green replacement of toxic and unst

Synthesis of CF3-Containing Spirocyclic Indolines via a Red-Light-Mediated Trifluoromethylation/Dearomatization Cascade

A red-light-mediated nPr-DMQA+-catalyzed cascade intramolecular trifluoromethylation and dearomatization of indole derivatives with Umemoto's reagent has been developed. This protocol provides a facile and efficient approach for the construction of functionalized and potentially biologically important CF3-containing 3,3-spirocyclic indolines with moderate to high yields and excellent diastereoselectivities under mild conditions. The success of multiple gram-scale (1 and 10 g) experiments further highlights the robustness and practicality of this protocol and the merit of the employment of red light. Mechanistic studies support the formation of a crucial CF3 radical species and a dearomatized benzyl carbocation intermediate.

Metal–Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis

We report the design of a bifunctional metal–organic layer (MOL), Hf12-Ru-Co, composed of [Ru(DBB)(bpy)2]2+ [DBB-Ru, DBB=4,4′-di(4-benzoato)-2,2′-bipyridine; bpy=2,2′-bipyridine] connecting ligand as a photosensitizer and Co(dmgH)2(PPA)Cl (PPA-Co, dmgH=dimethylglyoxime; PPA=4-pyridinepropionic acid) on the Hf12 secondary building unit (SBU) as a hydrogen-transfer catalyst. Hf12-Ru-Co efficiently catalyzed acceptorless dehydrogenation of indolines and tetrahydroquinolines to afford indoles and quinolones. We extended this strategy to prepare Hf12-Ru-Co-OTf MOL with a [Ru(DBB)(bpy)2]2+ photosensitizer and Hf12 SBU capped with triflate as strong Lewis acids and PPA-Co as a hydrogen transfer catalyst. With three synergistic active sites, Hf12-Ru-Co-OTf competently catalyzed dehydrogenative tandem transformations of indolines with alkenes or aldehydes to afford 3-alkylindoles and bisindolylmethanes with turnover numbers of up to 500 and 460, respectively, illustrating the potential use of MOLs in constructing novel multifunctional heterogeneous catalysts.

Practical Chemoselective Acylation: Organocatalytic Chemodivergent Esterification and Amidation of Amino Alcohols with N-Carbonylimidazoles

Chemoselective transformations are a cornerstone of efficient organic synthesis; however, achieving this goal for even simple transformations, such as acylation reactions, is often a challenge. We report that N-carbonylimidazoles enable catalytic chemodivergent aniline or alcohol acylation in the presence of pyridinium ions or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), respectively. Both acylation reactions display high and broad chemoselectivity for the target group. Unprecedented levels of chemoselectivity were observed in the DBU-catalyzed esterification: A single esterification product was obtained from a molecule containing primary aniline, alcohol, phenol, secondary amide, and N?H indole groups. These acylation reactions are highly practical as they involve only readily available, inexpensive, and relatively safe reagents; can be performed on a multigram scale; and can be used on carboxylic acids directly by in situ formation of the acylimidazole electrophile.

Alkylation of Indoles with α,β-Unsaturated Ketones using Alumina in Hexanes

We evaluated the influence of solvent on the alumina-promoted C3-alkylation of indoles with α,β-unsaturated ketones. We found that lipophilic solvents were generally superior to hydrophilic ones with hexanes offering the 3-alkyl indole products in high yields. Thus, we demonstrate an inexpensive and procedurally simple new process that pairs acidic alumina with hexanes to achieve this important Michael alkylation. The substrate scope includes twenty-four examples with reaction yields ranging from 61 to 96%. (Figure presented.).

Ruthenium-Catalyzed Selective C?C Coupling of Allylic Alcohols with Free Indoles: Influence of the Metal Catalyst

Versatile reactive activities of allyl alcohols with free indoles in C?H functionalization reactions were investigated. Direct alkylation or cascade cyclization reactions could be selectively controlled based on the catalyst system: Ru(PPh3)3Cl2 provided C3-substituted β-ketone indoles whereas [Ru(p-cymene)Cl2]2 yielded cyclized indoles.

Supported iron catalysts for Michael addition reactions

Heterogeneous catalysts have been widely used for chemical transformations and offer easy product separation in addition to their high activity. Iron is an earth-abundant metal, but it has not been studied thoroughly as heterogeneous catalysts for organic

TiCl2(OTf)-SiO2: A solid stable lewis acid catalyst for Michael addition of α-Aminophosphonates, Amines, Indoles and Pyrrole

TiCl2(OTf)-SiO2 is simply prepared by immobilization of TiCl3(OTf) on silica gel surface and introduced as a non-hygroscopic Lewis acid catalyst for C-N and C-C bond formation via Michael addition reaction. A variety of structurally diverse nitrogen nucleophiles including α-aminophosphonates, aliphatic and aromatic amines and imidazole were evaluated as Michael donors. Friedel–Crafts alkylation of indoles and pyrrole was also investigated through Michael addition reaction in the presence of TiCl2(OTf)-SiO2 as a catalyst. The reactions were conducted at room temperature or 60 °C under solvent-free conditions and the desired Michael adducts were obtained in high to excellent yields.

Regioselective Cyclization of (Indol-3-yl)pentyn-3-ols as an Approach to (Tetrahydro)carbazoles

An acid-catalyzed, highly regioselective cycloisomerization as well as dehydro-cyclization of (indol-3-yl)pentyn-3-ols has been reported for the selective synthesis of tetrahydrocarbazoles and carbazoles. This process is mild and found to be very general in terms of structural diversity of substrates. Utilizing the strategy, an efficient synthetic approach for the functionalized frameworks of carbazomycins A-D has also been developed.