10259-08-2

Basic information

• Product Name: Cyclohexanol, 1-nitroso-, acetate (ester)
• CAS NO: 10259-08-2
• Molecular Formula: C8H13NO3
• Molecular Weight: 171.196
• Mol File: 10259-08-2.mol

Chemical Properties

• CAS DataBase Reference: Cyclohexanol, 1-nitroso-, acetate (ester)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanol, 1-nitroso-, acetate (ester)(10259-08-2)
• EPA Substance Registry System: Cyclohexanol, 1-nitroso-, acetate (ester)(10259-08-2)

Safety Data

• Hazardous Substances Data: 10259-08-2(Hazardous Substances Data)

Upstream product

• 100-64-1 cyclohexanone-oxime 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 41018-52-4 (4-bromophenyl)-λ³-iodanediyl diacetate 
• 108-24-7 acetic anhydride 
• 1122-60-7 1-nitrocyclohexane 
• 563-63-3 silver(I) acetate 
• 546-67-8 lead(IV) tetraacetate 

Downstream Products

• 13891-50-4 N-phenyl-N-(1-phenylcyclohexyl)hydroxylamine 
• 108-94-1 cyclohexanone 
• 105-60-2 caprolactam 
• 1264294-14-5 1-nitrosocyclohexyl pivalate 
• 100-64-1 cyclohexanone-oxime 
• 13891-49-1 acetic acid-(1-nitro-cyclohexyl ester) 
• 13972-59-3 N-Methyl-N-(1-methyl-cyclohexyl)-hydroxylamin 

Relevant articles and documents

[3,2]-Sigmatropic rearrangement of acyloxy nitronic acids into geminal acyloxy nitroso compounds

Acylation of secondary nitroalkanes is accompanied by [3,2]-sigmatropic rearrangement of acyloxy nitronic acids into geminal acyloxy nitroso compounds which are formed in preparative yields.

Photo-Mediated Intermolecular Coupling of Alkenes with Ketones via Acyloxy Nitroso Compounds

An atom-economic intermolecular radical addition reaction of acyloxy nitroso compounds to electron-deficient alkenes mediated by visible light is reported. The starting nitroso derivatives are readily prepared by oxidation of the corresponding oximes prepared from ketones and the overall transformation represents an oxidative coupling of a ketone with a Michael acceptor. The cascade proceeds smoothly under mild conditions, providing a series of valuable functionalized oximes in moderate to good yields. Mechanistic studies suggest that these cascades proceed via addition/coupling processes that are controlled by the persistent radical effect (PRE) with NO acting as the persistent species.

α-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights

α-Acyloxynitroso derivatives are a class of heterodienophiles leading to valuable 3,6-dihydro-1,2-oxazines or the corresponding aminoalcohols in good yields. The discovery that a β-oxygenated moiety led to a domino [4+2] cycloaddition/σN-O bond cleavage in the presence of a catalytic amount of Lewis acid was investigated in detail, through kinetic profiling of the reaction both in the absence and presence of a promoter. These studies showed that the role of the Lewis acid was to accelerate the σN-O bond cleavage thereby promoting a highly reproducible sequence. In addition, our preliminary results on an asymmetric version of this domino sequence are reported.

Synthesis of cyclic hydroxamic acids through -NOH insertion of ketones

Treatment of cyclobutanone or cyclopentanone with N- hydroxybenzenesulfonamide under basic conditions yields the ring-expanded cyclic hydroxamic acid in 18-69% yield. Reactions of substituted cyclobutanones give ring expanded products where the -NOH group regio- and stereoselectively inserts to the more substituted position. This expansion likely proceeds through a mechanism that includes addition of the N-anion of N-hydroxybenzenesulfonamide to the ketone and a C-nitroso intermediate that rearranges to the final product.

C-NITROSO-DERIVED NITROXYL DONORS

Active compounds of Formula (I) are described: wherein: R1 and R2 are each independently C1-C4 alkyl; or R1 and R2 together form a C2-C7 alkylene chain; and Z is a non-steroidal anti-inflammatory drug (NSAID); a

Hydrolysis of acyloxy nitroso compounds yields nitroxyl (HNO)

Nitroxyl (HNO/NO-), the reduced form of nitric oxide, has gained attention based on its separate chemistry and biology from nitric oxide. The inherent reactivity of HNO requires new and mechanistically unique donors for the detailed study of HN

Oxidative Cleavage of Ketoximes with Iodosobenzene Diacetate

Hypervalent iodine oxidation of ketoximes (1) using iodosobenzene diacetate leads to cleavage of 1 with the formation of corresponding ketones (2) under neutral conditions in good yields.The scope and limitations of the reaction are discussed as well as the mechanism.

Cinetique d'oxydation des oximes du benzaldehyde et del'acetophenone par l'ion thallique

The kinetics of oxidation of benzaldehyde and acetophenone oximes by Tl(III) in aqueous medium has been studied.The reaction occurs in two consecutive steps: formation of a nitroso intermediate and its decomposition.The oxime forms a complex with Tl(III)