6944-54-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(2E)-N-hydroxy-4-phenylbutan-2-imine is used as an intermediate in the synthesis of pharmaceutical compounds, leveraging its unique chemical structure to facilitate the creation of various medications.
Used in Enzyme Inhibition:
In the field of pharmacology, (2E)-N-hydroxy-4-phenylbutan-2-imine is used as an inhibitor of the enzyme 17β-hydroxysteroid dehydrogenase type 3. This enzyme plays a crucial role in the biosynthesis of testosterone, making the compound a potential candidate for treatments related to hormonal imbalances or conditions influenced by testosterone levels.
Used in Organic Synthesis:
As a reagent in organic synthesis, (2E)-N-hydroxy-4-phenylbutan-2-imine contributes to the development of new chemical entities and materials, showcasing its utility in advancing the field of chemistry.

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 7064-06-4 3-methyl-5-phenyl-4,5-dihydroisoxazole 
• 63819-79-4 (3-nitrobutyl)benzene 
• 1028432-06-5 C₂₃H₃₅NO₃SSi 
• 104-51-8 1-butylbenzene 

Downstream Products

• 65266-76-4 N-(1-Methyl-3-phenyl-propyl)-hydroxylamine 
• 20296-07-5 1-hydroxy-4-phenyl-2-butanone 
• 71255-62-4 1-Phenylbutan-3-one oxime O-acetate 
• 2550-26-7 4-Phenyl-2-butanone 
• 91-63-4 2-methylquinoline 
• 877-95-2 methyl-N-(benzyl-methyl)-formamide 
• 63819-79-4 (3-nitrobutyl)benzene 
• 1068001-35-3 4-phenylbutan-2-one O-(2-hydroxy-3-phenoxypropyl)oxime 
• 71255-68-0 C₁₂H₁₇NO₂ 
• 73313-03-8 O-<2-hydroxy-3-(isopropylamino)propyl>benzylacetone oxime 
• 73313-05-0 4-Phenyl-butan-2-one O-(3-tert-butylamino-2-hydroxy-propyl)-oxime 

Relevant academic research and scientific papers

SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams

A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.

The ruthenium-catalyzed C-H functionalization of enamides with isocyanates: Easy entry to pyrimidin-4-ones

Ruthenium-catalyzed heteroannulation between enamides and isocyanates has been realized as a complementary approach to conventional strategies for the synthesis of pyrimidin-4-ones. High step-A nd atom-economy was achieved for the rapid construction of such privileged scaffolds, which are found in a multitude of pharmaceutical compounds. The generality and practicability of this transformation were reflected by the broad scope of substrates with diverse functional groups, large-scale synthesis, and late-stage diversification.

Beckmann rearrangement of ketoxime catalyzed by N-methyl-imidazolium hydrosulfate

Beckmann rearrangement of ketoxime catalyzed by acidic ionic liquid-N-methyl-imidazolium hydrosulfate was studied. Rearrangement of benzophenone oxime gave the desirable product with 45% yield at 90 ?C. When co-catalyst P2O5 was added, the yield could be improved to 91%. The catalyst could be reused three cycles with the same efficiency. Finally, reactions of other ketoximes were also investigated.

Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions

A novel copper-catalyzed annulation of oxime acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(iii) intermediates were involved. In addition, this protocol proceeded under redox-neutral conditions and did not require additives or ligands.

Catalytic Enantio- and Diastereoselective Mannich Addition of TosMIC to Ketimines

Chiral amines bearing a stereocenter in the α position are ubiquitous compounds with many applications in the pharmaceutical and agrochemical sectors, as well as in catalysis. Catalytic asymmetric Mannich additions represent a valuable method to access such compounds in enantioenriched form. This work reports the first enantio- and diastereoselective addition of commercially available p-toluenesulfonylmethyl isocyanide (TosMIC) to ketimines, affording 2-imidazolines bearing two contiguous stereocenters, one of which is fully-substituted, with high yields and excellent stereocontrol. The reaction, catalyzed by silver oxide and a dihydroquinine-derived N,P-ligand, is broad in scope, operationally simple, and scalable. Derivatization of the products provides enantioenriched vicinal diamines, precursors to NHC ligands and sp3-rich heterocyclic scaffolds. Computations are used to understand catalysis and rationalize stereoselectivity.

Catalyst free synthesis of mono- and disubstituted pyrimidines from O-acyl oximes

Transition-metal or iodine catalyzed transformations of O-acyl oximes to various N-heterocycles are well established. Herein, we report a catalyst free, oxime carboxylate based, three-component condensation method to access mono- and disubstituted pyrimidines. A broad range of substituted pyrimidines were prepared in moderate to excellent yields. Control experiments reveal that in situ generated formamidine is the key intermediate.

Divergent Iron-Catalyzed Coupling of O-Acyloximes with Silyl Enol Ethers

An iron-catalyzed coupling reaction of O-acyloximes and O-benzoyl amidoximes with silyl enol ethers is reported. The protocol provides access to functionalized pyrroles, 1,6-ketonitriles, pyrrolines and imidazolines via carbon-centered radicals generated from an initially formed iminyl radical. The intramolecular cyclization and ring-opening processes of the iminyl radical take place preferentially over reactions that proceed through a 1,3-hydrogen transfer, providing insights into iron-catalyzed reactions with oxime derivatives. The cheap and environmentally friendly iron catalyst, the broad substrate scope and the functional group compatibility make this protocol useful for synthesis of valuable nitrogen-containing products.

Iron-Catalyzed Synthesis of 2H-Imidazoles from Oxime Acetates and Vinyl Azides under Redox-Neutral Conditions

A novel and versatile method for the synthesis of 2H-imidazoles via iron-catalyzed [3 + 2] annulation from readily available oxime acetates with vinyl azides has been developed. This denitrogenative process involved N-O/N-N bond cleavages and two C-N bond formations to furnish 2,4-substituted 2H-imidazoles. This protocol was performed under mild reaction conditions and needed no additives or ligands. Furthermore, this is a green reaction involving oxime acetate as internal oxidant, acetic acid, and nitrogen as byproducts.

Synthesis of Air- and Moisture-Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction

Air-/moisture-stable, crystalline, and storable chiral salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α-amino esters, γ- and δ-lactams, and isoindolinones have also been carried out using this methodology. Finally, the method has been applied to synthetic targets of pharmaceutical relevance, such as R-(+)-salsolidine and R-(+)-crispine A.

One-pot oximation-Beckmann rearrangement of ketones and aldehydes to amides of industrial interest: Acetanilide, caprolactam and acetaminophen

High yielding one-pot oximation-Beckmann rearrangement of ketones to amides in ktrifluoroacetic acid has been conducted on several ketones and aldehydes. The substrate reactivity showed to depend on both oximation and Beckmann rearrangement reaction rate. In this synthetic procedure, trifluoroacetic acid acts as solvent, acid catalyst and organocatalyst and can be easily recycled.