4312-92-9

Usage

InChI:InChI=1/C5H11NO2/c1-2-3-4-5(7)6-8/h8H,2-4H2,1H3,(H,6,7)

Upstream product

• 624-24-8 methyl valerate 
• 110-62-3 pentanal 
• 539-82-2 ethyl n-valerate 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 71-41-0 pentan-1-ol 
• 84298-28-2 1H-1,2,3-benzotriazol-1-yl(n-butyl)methanone 
• 109-52-4 valeric acid 

Downstream Products

• 109-52-4 valeric acid 
• 96-48-0 4-butanolide 
• 51637-47-9 2-chlorobutanecarboxylic acid 

Relevant academic research and scientific papers

Synthesis of benzothiadiazine-1-oxides by rhodium-catalyzed C-H amidation/cyclization

A rhodium-catalyzed C-H amidation/cyclization sequence provides benzothiadiazine-1-oxides from sulfoximines and 1,4,2-dioxazol-5-ones in good yields. The reaction is characterized by a high functional group tolerance and, in contrast to most previous transformations of this type, is well-suited for S-alkyl-S-arylsubstituted sulfoximines.

Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C-H Amidation

A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.

Iridium-Catalyzed Enantioselective C(sp3)-H Amidation Controlled by Attractive Noncovalent Interactions

While remarkable progress has been made over the past decade, new design strategies for chiral catalysts in enantioselective C(sp3)-H functionalization reactions are still highly desirable. In particular, the ability to use attractive noncovalent interactions for rate acceleration and enantiocontrol would significantly expand the current arsenal for asymmetric metal catalysis. Herein, we report the development of a highly enantioselective Ir(III)-catalyzed intramolecular C(sp3)-H amidation reaction of dioxazolone substrates for synthesis of optically enriched γ-lactams using a newly designed α-amino-acid-based chiral ligand. This Ir-catalyzed reaction proceeds with excellent efficiency and with outstanding enantioselectivity for both activated and unactivated alkyl C(sp3)-H bonds under very mild conditions. It offers the first general route for asymmetric synthesis of γ-alkyl γ-lactams. Water was found to be a unique cosolvent to achieve excellent enantioselectivity for γ-aryl lactam production. Mechanistic studies revealed that the ligands form a well-defined groove-type chiral pocket around the Ir center. The hydrophobic effect of this pocket allows facile stereocontrolled binding of substrates in polar or aqueous media. Instead of capitalizing on steric repulsions as in the conventional approaches, this new Ir catalyst operates through an unprecedented enantiocontrol mechanism for intramolecular nitrenoid C-H insertion featuring multiple attractive noncovalent interactions.

Photoinduced one-pot synthesis of hydroxamic acids from aldehydes through in-situ generated silver nanoclusters

Hydroxamic acids have attracted significant attention due to their widespread use in applied chemistry. In this report, a modified Angeli–Rimini method has been achieved via the visible light-mediated catalytic transformation of a variety of heterocyclic, aromatic and aliphatic aldehydes 1a–j to their corresponding hydroxamic acids 2a–j in 81–93% yield. The unique ability of vitamin K3 as a photoredox catalyst to expedite the development of completely new reaction mechanisms and to enable the construction of challenging carbon–nitrogen bonds has been investigated. It is shown for the first time that the vitamin K3 and aldehyde are largely responsible for rapid in situ reduction of Ag+ ions to catalytic photoluminescent Ag nanoclusters that possess a bandgap energy of 2.87?eV and are less than 2 nm in size. A mechanism for this reaction has been proposed and is supported by UV–Vis, TEM, ESI/MS, FT-IR, 1H NMR and 13C NMR analyses. The investigated method utilizes readily available reagents and produces the hydroxamic acids in high yields without the formation of side products, making it simple, practical and cost-effective.

A two-step tandem reaction to prepare hydroxamic acids directly from alcohols

The first synthesis of hydroxamic acids from alcohols has been developed. Both benzylic and aliphatic alcohols can be tolerated and applied in this reaction. The methodology is economical, environmentally benign and high yielding. This journal is

Synthesis and characterization of valero and isovalero hydroxamic acids and their complexes with Zn(II) and Al(III)

Valerohydroxamic acid (VAH) and isovalerohydroxamic acid (IVAH) were synthesized and characterized by m.p. and pKa determination, IR and 1H NMR studies. The ligands were complexed with Zn2+ and Al3+ and the complexes were characterized by metal analysis, IR and conductance studies. Antimicrobial studies of all the compounds were carried out. The pKa of the ligands are 9.50 ± 0.01 (VAH) and 9.5.1± 0.01 (IVAH) at 25 °C and ionic strength is 0.1 mol/dm 3, while their melting points are 77.8 °C and 76.8 °C, respectively. IR and 1H NMR data are consistent with the proposed formula. The complexes are non-electrolytes in EtOH. Coordination mode (0,0) is consistent with the IR data of the complexes. The compounds exhibited no significant antimicrobial activity.

Angeli-Rimini's reaction on solid support: A new approach to hydroxamic acids

Angeli-Rimini's reaction has been performed for the first time on solid phase. A convenient one-step procedure for the synthesis of hydroxamic acids starting from aldehydes and solid-supported N-hydroxybenzenesulfonamide is reported. The hydroxamates are isolated in good to high yields and purities by simple evaporation of the volatile solvents, after treatment of the crude reaction mixture with sequestering agents.

Efficient Conversions of Carboxylic Acids into O-Alkyl, N-Alkyl and O,N-Dialkylhydroxamic Acids

Carboxylic acids were conveniently converted into unsubstituted, N-alkyl-, O-alkyl-, and O,N-dialkylhydroxamic acids via acylbenzotriazole intermediates. The ready availability of the reagents, mild conditions, and easy handling of the intermediates are advantageous.