71559-13-2

Basic information

• Product Name: Cyclohexanol, 2-azido-
• CAS NO: 71559-13-2
• Molecular Formula: C6H11N3O
• Molecular Weight: 141.173
• Mol File: 71559-13-2.mol

Chemical Properties

• CAS DataBase Reference: Cyclohexanol, 2-azido-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanol, 2-azido-(71559-13-2)
• EPA Substance Registry System: Cyclohexanol, 2-azido-(71559-13-2)

Safety Data

• Hazardous Substances Data: 71559-13-2(Hazardous Substances Data)

Upstream product

• 4441-56-9 cyclohexylboronic acid 
• 286-20-4 cyclohexane-1,2-epoxide 
• 110-83-8 cyclohexene 

Downstream Products

• 1517-01-7 2-azidocyclohexan-1-one 
• 477584-30-8 tert-butyl (2-hydroxycyclohexyl)carbamate 
• 4050-48-0 2-nitrocyclohexanol 
• 1452855-85-4 2-{[1-(2-hydroxycyclohexyl)-1H-1,2,3-triazol-4-yl]methyl}-1H-isoindol-1,3(2H)-dione 
• 1394904-20-1 2-(4-((4-nitrophenoxy)methyl)-1H-1,2,3-triazol-1-yl)cyclohexanol 
• 1370596-21-6 diphenylmethanone O-{[1-(2-hydroxycyclohexyl)-1H-1,2,3-triazol-4-yl]methyl}oxime 
• 153789-13-0 tert-butyl 7-azabicyclo<4.1.0>heptane-7-carboxylate 
• 81097-47-4 N-benzenesulfonyl-7-azabicyclo<4.1.0>heptane 
• 108223-53-6 N-(cyclohex-2-en-1-yl)benzenesulfonamide 

Relevant articles and documents

Copper-catalyzed ring-opening reactions of alkyl aziridines with b2 pin2: Experimental and computational studies

The possibility to form new C–B bonds with aziridines using diboron derivatives con-tinues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individua-tion of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B2 pin2 ) in a regioselective nucleophilic addition reaction under copper catalysis.

Supported benzimidazole-salen Cu(II) complex: An efficient, versatile and highly reusable nanocatalyst for one-pot synthesis of hybrid molecules

A novel and efficient nanocatalyst consisting of benzimidazole-salen Cu(II) complex on surface-modified silica (BS-Cu(II)@SiO2) was prepared. The heterogeneous nanocatalyst was characterized by FESEM, TEM, EDX, FT-IR, XRD, ICP, and TGA. The nanocatalyst was used for the one-pot synthesis of some target hybrid molecules. An efficient four component C–H bond activation/[3?+?2] cycloaddition and condensation/cyclization/aromatization sequence toward triazole-benzimidazole derivatives is disclosed. This methodology provides a general and rapid synthetic route to some new triazole-benzimidazole hybrids under mild reaction conditions. In addition, the heterogeneous nanocatalyst can be easily separated from the reaction mixture and used several times without noticeable leaching or loss of its catalytic activity. We believe this interesting one-pot reaction as well as benzimidazole-salen Cu(II) complex pave the way to the design and synthesis of other new hybrid molecules and metal catalysts, respectively.

Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones

The esters of 1,2-azido alcohols were transformed into α-amido ketones without external oxidants through the Ru-catalyzed formation of N-H imines with the liberation of N2 followed by intramolecular migration of the acyl moiety. A wide range of α-amido ketones were obtained, and one-pot transformation into the corresponding oxazoles (or a thiazole) was demonstrated.

Design, synthesis and biological evaluation of novel 1,2,3-triazolyl β -hydroxy alkyl/carbazole hybrid molecules

The design, synthesis and biological study of several novel 1,2,3-triazolyl β -hydroxy alkyl/carbazole hybrid molecules as a new type of antifungal agent has been described. In this synthesis, the N-alkylation reaction of carbazol-9-ide potassium salt with 3-bromoprop-1-yne afforded 9-(prop-2-ynyl)-9H-carbazole. The ‘Click’ Huisgen cycloaddition reaction of 9-(prop-2-ynyl)-9H-carbazole with diverse β -azido alcohols in the presence of copper-doped silica cuprous sulphate led to target molecules in excellent yields. The in vitro antifungal and antibacterial activities of title compounds were screened against various pathogenic fungal strains, Gram-positive and/or Gram-negative bacteria. In particular, 1-(4-((9H-carbazol-9-yl) methyl)-1H-1,2,3-triazol-1-yl)-3-butoxypropan-2-ol (10e) proved to have potent antifungal activity against all fungal tests compared with fluconazole and clotrimazole as studied reference drugs. Our molecular docking analysis revealed an appropriate fitting and a potential powerful interaction between compound 10e and an active site of the Mycobacterium P450DM enzyme. The strong hydrogen bondings between β -hydroxyl and ether groups in 10e were found to be the main factors that drive the molecule to fit in the active site of enzyme. The in silico pharmacokinetic studies were used for a better description of 10a–10n as potential lead antifungal agents for future investigations.

Copper/graphene/clay nanohybrid: A highly efficient heterogeneous nanocatalyst for the synthesis of novel 1,2,3-triazolyl carboacyclic nucleosides via 'Click' Huisgen 1,3-dipolar cycloaddition

A very mild and highly efficient synthesis of some novel 1H-1,2,3-triazolyl carboacyclic nucleosides via a 'Click' Huisgen cycloaddition of N-propargyl nucleobases and azido alcohols using Cu/aminoclay/reduced graphene oxide nanohybrid (Cu/AC/r-GO nanohybrid) as nanocatalyst is described. The preparation and characterization of Cu/AC/r-GO nanohybrid are discussed. This catalyst was characterized by X-ray diffraction, FT-IR, TEM, and energy-dispersive analysis of X-ray techniques. Cu/AC/r-GO nanohybrid is a stable and highly efficient heterogeneous nanocatalyst that can be easily prepared, used, and restored from the reaction mixture by simple filtration, and reused for many consecutive trials without significant decrease in activity.

Synthesis of 1,2-azidoalcohols from epoxides using a task-specific protic ionic liquid: 1-hydrogen-3-methylimidazolium azide

A task-specific ionic liquid as an environmentally eco-friendly green catalyst has been synthesized and used in the ring opening of epoxides under green conditions. In order to use protic ionic liquids (PIL), we decided to synthesize 1,2-azidoalcohols via

One-pot synthesis of tweezer-like calix[4]resorcinarene decorated with pendant heterocyclic moieties: An efficient and recyclable heterogeneous PTC for the preparation of azidohydrins in water

Direct incorporation of ionic liquid onto the upper rim of calix[4]resorcinarene led to the formation of tweezer-like calix[4]resorcinarene via one-pot strategy. The formation of this cationic supramolecular structure was confirmed by 1H NMR,

'Click synthesis' of some novel o-substituted oximes containing 1,2,3-triazole-1,4-diyl residues as new analogs of β-adrenoceptor antagonists

The 'click synthesis' of some novel O-substituted oximes, 7a-7t, which contain 1,2,3-triazolediyl residues, as new analogs of β-adrenoceptor antagonists is described (Schemes 1-4). The synthesis of these compounds was achieved in four to five steps. The formation of oximes of 9H-fluoren-9-one and benzophenone, i.e., 9a and 9b, respectively, followed by their reaction with propargyl bromide, afforded O-propargyl oximes 10a and 10b, respectively, which by a subsequent CuI-catalyzed Huisgen cycloaddition with prepared β-azido alcohols 11a-11j (Schemes 2 and 3), led to the target compounds 7a-7t in good yields. Copyright

Phosphine-catalyzed heine reaction

Aziridines are important synthetic intermediates which readily undergo ring-opening reactions. It is demonstrated that electron-rich phosphines are efficient catalysts for the regioselective rearrangement of N-acylaziridines to oxazolines. The reactions o

Heteroarylalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists

The invention provides heteroarylene substituted 8-azabicyclo[3.2.1]octane compounds of formula (I): wherein R1, R2, A, and m are defined in the specification, or a pharmaceutically-acceptable salt thereof, that are antagonists at th