4312-93-0

Usage

InChI:InChI=1/C6H13NO2/c1-2-3-4-5-6(8)7-9/h9H,2-5H2,1H3,(H,7,8)

Upstream product

• 142-62-1 hexanoic acid 
• 106-70-7 methyl hexanoate 
• 142-61-0 Hexanoyl chloride 
• 60988-34-3 1-(1-imidazolyl)-1-hexanone 
• 646-14-0 1-nitrohexane 
• 123-66-0 Ethyl hexanoate 

Downstream Products

• 51637-48-0 3-chlorohexanoic acid 
• 142-62-1 hexanoic acid 
• 108-29-2 5-methyl-dihydro-furan-2-one 

Relevant academic research and scientific papers

Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas

Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.

P(III)-Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids

An external oxidant-free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri-substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N-based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.

Efficient Copper-Catalyzed Multicomponent Synthesis of N-Acyl Amidines via Acyl Nitrenes

Direct synthetic routes to amidines are desired, as they are widely present in many biologically active compounds and organometallic complexes. N-Acyl amidines in particular can be used as a starting material for the synthesis of heterocycles and have several other applications. Here, we describe a fast and practical copper-catalyzed three-component reaction of aryl acetylenes, amines, and easily accessible 1,4,2-dioxazol-5-ones to N-acyl amidines, generating CO2 as the only byproduct. Transformation of the dioxazolones on the Cu catalyst generates acyl nitrenes that rapidly insert into the copper acetylide Cu-C bond rather than undergoing an undesired Curtius rearrangement. For nonaromatic dioxazolones, [Cu(OAc)(Xantphos)] is a superior catalyst for this transformation, leading to full substrate conversion within 10 min. For the direct synthesis of N-benzoyl amidine derivatives from aromatic dioxazolones, [Cu(OAc)(Xantphos)] proved to be inactive, but moderate to good yields were obtained when using simple copper(I) iodide (CuI) as the catalyst. Mechanistic studies revealed the aerobic instability of one of the intermediates at low catalyst loadings, but the reaction could still be performed in air for most substrates when using catalyst loadings of 5 mol %. The herein reported procedure not only provides a new, practical, and direct route to N-acyl amidines but also represents a new type of C-N bond formation.

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.

Lossen rearrangements under heck reaction conditions

The classical Lossen rearrangement converts activated hydroxamic acids to isocyanates that form numerous products upon their reaction with nucleophiles. We report a simple and highly efficient method of using Heck reaction conditions to initiate Lossen rearrangements of hydroxamic acids. In addition, Lossen rearrangements occur in the presence of palladium(II) acetate or triethylamine, components of the Heck reaction, alone. A potential mechanism is provided to explain this reactivity and these results show that Heck reactions and Lossen rearrangements occur under the same conditions and may provide new methods for facile initiation of Lossen rearrangements.

Protective solutions for organs

Described is a protective solution for avoiding ischemic, storage or ischemia/reperfusion to organs, or to isolated cell systems, or to tissue components after perfusion, surgery, transplantation, or cryopreservation and subsequent reperfusion, which contains alkali ions, and if need be also alkaline earth ions as the electrolyte, a buffer e.g. on a histidine derivation basis, as well as a polyol and/or a saccharide, has an osmolarity of about 290 mosm/l to about 350 mosm/l, as well as a pH value of about 6.8 to about 7.4, and to which hydroxamic acid, and/or one or more hydroxamic acid derivatives are added.

A convenient method for the preparation of hydroxamic acids

A one-step conversion of carboxylic acid to hydroxamic acid, under neutral pH conditions is described. This simple, selective and efficient method was applied to a wide range of aliphatic/aromatic carboxylic acid derivatives that contain hydroxyl, halo, ester and other base sensitive groups as substituents. The method utilizes cheaply available reagents and hence it is a practical and cost effective strategy, compared to the other methods available in the literature. (C) 2000 Elsevier Science Ltd.

Solid supported synthesis of hydroxamic acids

A novel approach to the solid supported synthesis of hydroxamic acids was developed. It employs oxime resin and unlike all previously reported methods allows for the use of acid labile protecting groups. Cleavage is induced by treatment with tert-butyldim

14N Quadrupole Double Resonance in Some Substituted Hydroxamic Acids

14N quadrupole coupling constants and asymmetry parameters have been measured in a number of hydroxamic acids by double-resonance field-cycling techniques based on either irradiation in zero magnetic field or cross relaxation.The compounds all display high asymmetry parameters.Those in which this quantity is greater than 0.9 show remarkable line shapes for the two lower 14N frequencies (νy, νz) in their irradiation spectra.They are explained in terms of a thermal-mixing mechanism, which generates polarization of the 1H dipolar levels when these nearly degenerate frequencies are strongly irradiated in zero field, and then subsequently modified by level crossing when the sample is returned to high field to measure the remaining 1H signal.Ab initio SCF-MO calculations of the 14N quadrupole tensor in a group of molecules at the orientation found in crystals of acetohydroxamic acid hemihydrate and oxalodihydroxamic acid are in reasonable agreement with experiment and predict that in all the hydroxamic acids studied the maximum principal component is negative and closely parallel to the direction of the 2p? orbital.