4500-12-3

Basic information

• Product Name: 2-Adamantanone oxime
• Synonyms: ADAMANTAN-2-ONE OXIME;AKOS BBS-00002625;AKOS BC-0475;2-ADAMANTANONE OXIME;IFLAB-BB F0451-0957;TIMTEC-BB SBB009853;2-Hydroxyiminoadamantane;2-Isonitrosoadamantane
• CAS NO: 4500-12-3
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• EINECS: 224-807-4
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;Adamantanes;Nitrogen Compounds;Organic Building Blocks;Oximes
• Mol File: 4500-12-3.mol

Chemical Properties

• Melting Point: 164-167 °C
• Boiling Point: 294 °C at 760 mmHg
• Flash Point: 175.6 °C
• Appearance: white solid
• Density: 1.5 g/cm³
• Vapor Pressure: 0.000409mmHg at 25°C
• Refractive Index: 1.752
• Solubility: soluble in Methanol
• PKA: 12.46±0.20(Predicted)
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 2-Adamantanone oxime(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Adamantanone oxime(4500-12-3)
• EPA Substance Registry System: 2-Adamantanone oxime(4500-12-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: AU5018500
• F: 10-21
• HazardClass: IRRITANT
• Hazardous Substances Data: 4500-12-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Adamantanone oxime is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new medications with diverse therapeutic profiles.
Used in Agrochemical Industry:
2-Adamantanone oxime is utilized as an intermediate in the production of agrochemicals, indicating its potential role in the development of pesticides or other agricultural chemicals that can enhance crop protection and yield.
Used in Parkinson's Disease Treatment:
2-Adamantanone oxime is studied for its potential use as a therapeutic agent in the treatment of Parkinson's disease, highlighting its role in managing the symptoms and progression of this neurological condition.
Used in Influenza Treatment:
2-Adamantanone oxime is also considered for its potential applications in treating influenza, suggesting its antiviral properties that could be harnessed to combat the influenza virus.
Used in Antiviral Applications:
2-Adamantanone oxime has been studied for its antiviral properties, making it a candidate for further research and development in creating antiviral medications.
Used in Antiproliferative Applications:
Due to its antiproliferative properties, 2-Adamantanone oxime is explored for its potential to inhibit the proliferation of certain cells, which could be beneficial in treating conditions where uncontrolled cell growth is a concern.
Used in the Preparation of Amantadine:
2-Adamantanone oxime is used in the preparation of amantadine, a medication that is specifically used to treat Parkinson's disease and influenza A virus infections, underlining its importance in the synthesis of this specific drug.

InChI:InChI=1/C10H15NO/c12-11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9,12H,1-5H2/b11-10-

Upstream product

• 917-64-6 methyl magnesium iodide 
• 33673-34-6 2-chloro-2-nitrosoadamantane 
• 700-58-3 2-Adamantanone 
• 693-03-8 n-butyl magnesium bromide 
• 97-93-8 triethylaluminum 
• 100-58-3 phenylmagnesium bromide 
• 33974-41-3 neopentylmagnesium bromide 
• 2259-30-5 tert-butylmagnesium bromide 
• 1589-82-8 phenylmagnesium bromide 
• 107092-97-7 2-Hydroxyamino-adamantan-2-ol 
• 13074-39-0 N-(2-adamantyl)amine 

Downstream Products

• 33673-34-6 2-chloro-2-nitrosoadamantane 
• 103586-48-7 3-[1-Phenyl-meth-(E)-ylideneaminooxy]-propionic acid ethyl ester 
• 125803-14-7 3-[1-Phenyl-meth-(Z)-ylideneaminooxy]-propionic acid ethyl ester 
• 94719-80-9 (E)-O-(o-methoxycinnamoyl)-2-adamantanone oxime 
• 700-58-3 2-Adamantanone 
• 88247-89-6 2-nitroiminoadamantane 
• 700-57-2 1-adamantanol 
• 88247-90-9 2-nitroaminoadamantane 
• 40854-02-2 2-bromo-2-nitro-adamantane 
• 94719-73-0 O-(p-cyanobenzoyl)-2-adamantanone oxime 
• 94719-79-6 O-cinnamoyl-2-adamantanone oxime 
• 94719-76-3 O-(p-chlorophenylacetyl)-2-adamantanone oxime 
• 94719-75-2 O-(m-nitrobenzoyl)-2-adamantanone oxime 
• 116437-10-6 2-chloro-2-nitro-adamantane 

Relevant articles and documents

Potential Synthetic Adaptogens: V. Synthesis of Cage Monoamines by the Schwenk–Papa Reaction

The reduction of cage ketoximes under Schwenk–Papa reaction conditions was studied to establish that the d,l, d- and l-camphor oximes are smoothly reduced to the corresponding amines in high yields. At the same time, d,l-norcamphor and adamantan-2-one oximes undergo partial catalytic deoximation to form a mixture of the corresponding amines and alcohols.

Synthesis and biological evaluation of phenylpropanoid derivatives

In this work, a series of oxime ether phenylpropanoid derivatives were synthesized. Their anti-hepatitis B virus (HBV) activity in HepG 2.2.15 cells was determined, and anti-cancer potential against three human cancer cell lines was evaluated. All the synthesized derivatives showed great efficiency against HBV. Compound 4d demonstrated the most effective anti-HBV activity, performing strong potent inhibitory not only on the secretion of HBsAg (IC50?=?50.45?μM, SI?=?9.18) and HBeAg (IC50?=?50.11?μM, SI?=?9.24), but also on the HBV DNA replication (IC50?=?51.80?μM, SI?=?8.94). Besides, the synthetic compounds also displayed obvious anti-cancer activity. Moreover, the docking study of all synthesized compounds inside the related protein active site was conducted to explore the molecular interactions and a molecular target for activity using a MOE-docking technique. This study identified a new class of potent anti-HBV and anti-cancer agents.

Ruthenium Trichloride Catalyzed Highly Efficient Deoximation of Oximes to the Carbonyl Compounds and Nitriles without Acceptors

An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields. An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields.

CENTRALLY ACTIVE AND ORALLY BIOAVAILABLE ANTIDOTES FOR ORGANOPHOSPHATE EXPOSURE AND METHODS FOR MAKING AND USING THEM

In alternative embodiments, the invention provides nucleophilic hydroxyimino- acetamido alkylamine antidotes that cross the blood-brain barrier (BBB) to catalyze the hydrolysis of organophosphate (OP)-inhibited human acetylcholinesterase (hAChE) in the central nerve system (CNS). The hydroxyimino-acetamido alkylamines of the invention are designed to fit within AChE active center gorge dimensions, bind with reasonable affinity, and react with the conjugated phosphate atom in the gorge. The hydroxyimino- acetamido alkylamines of the invention are also designed to possess ionization states that govern affinity and reactivity for the two linked hAChE re-activation steps. In alternative embodiments, the invention provides pumps, devices, subcutaneous infusion devices, continuous subcutaneous infusion devices, infusion pens, needles, reservoirs, ampoules, a vial, a syringe, a cartridge, a disposable pen or jet injector, a prefilled pen or a syringe or a cartridge, a cartridge or a disposable pen or jet injector, a two chambered or multi- chambered pump, a syringe, a cartridge or a pen or a jet injector, comprising a compound of the invention.

Oxidation of primary amines to oximes with molecular oxygen using 1,1-diphenyl-2-picrylhydrazyl and WO3/Al2O3 as catalysts

The oxidative transformation of primary amines to their corresponding oximes proceeds with high efficiency under molecular oxygen diluted with molecular nitrogen (O2/N2 = 7/93 v/v, 5 MPa) in the presence of the catalysts 1,1-diphenyl-2-picrylhydrazyl (DPPH) and tungusten oxide/alumina (WO3/Al2O3). The method is environmentally benign, because the reaction requires only molecular oxygen as the terminal oxidant and gives water as a side product. Various alicyclic amines and aliphatic amines can be converted to their corresponding oximes in excellent yields. It is noteworthy that the oxidative transformation of primary amines proceeds chemoselectively in the presence of other functional groups. The key step of the present oxidation is a fast electron transfer from the primary amine to DPPH followed by proton transfer to give the α-aminoalkyl radical intermediate, which undergoes reaction with molecular oxygen and hydrogen abstraction to give α-aminoalkyl hydroperoxide. Subsequent reaction of the peroxide with WO3/Al2O3 gives oximes. The aerobic oxidation of secondary amines gives the corresponding nitrones. Aerobic oxidative transformation of cyclohexylamines to cyclohexanone oximes is important as a method for industrial production of ε-caprolactam, a raw material for Nylon 6.

HISTONE DEACETYLASE INHIBITORS FOR THE TREATMENT OF FUNGAL INFECTIONS

Described are bridged compounds of the formula (I), their analogs, tautomeric forms, stereoisomers, geometrical isomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites and prodrugs thereof. The invention relates to compositions and methods to treat fungal infection. These compounds are selective HDAC inhibitors that act as inherent antifungal compounds or enhance the activity of other antifungal compounds such as azoles.

Application of the excited state meta effect in photolabile protecting group design

A novel photolabile protecting group for carbonyl compounds has been developed, based on the excited state meta effect.

Chlorination of oximes with aqueous H2O2/HCl system: Facile synthesis of gem-chloronitroso- and gem-chloronitroalkanes, gem-chloronitroso- and gem-chloronitrocycloalkanes

Chlorination of cyclic and linear ketone oximes with aqueous H 2O2/HCl in a two-phase dichloromethane-water system selectively affords gem-chloronitroso compounds in yields of up to 94%. One-pot oxidation of the resulting gem-chloronitroso compounds with peracetic acid, prepared in situ, gives gem-chloronitroalkanes and cycloalkanes in yields of up to 82%. The advantages of the method are that it is facile and environmentally benign and does not require gaseous chlorine. Georg Thieme Verlag Stuttgart.

QUINAZOLINE DERIVATIVES AS ACETYLCHOLINESTERASE INHIBITORS

A method of treating cognitive deficiencies is described by administering a quinazoline derivative of the general formula wherein A represents in which n is 1-10, P is a bond or (CH2)m in which m is 0-10, and M is =0 , =S , =NR, =CRR, novel compounds of the above are also described as well as methods of manufacture and pharmaceutical compositions.

Oxidation of Primary Aliphatic Amines to C-Nitroso Dimers

A biphasic system of ethyl acetate or dichloromethane and water containing sodium percarbonate (Na2CO3*3/2H2O2), sodium hydrogen carbonate and N,N,N',N'-tetraacetylethylenediamine oxidizes primary aliphatic amines to aliphatic C-nitroso dimers in most cases in good to excellent yields.