7575-82-8

Usage

Uses

Used in Pharmaceutical Industry:
1-Nitroadamantane is used as an antiviral agent for its ability to inhibit viral replication and protect against viral infections.
Used in Immunology Research:
1-Nitroadamantane is used as an immunosuppressive agent for its capacity to inhibit the proliferation of lymphocytes, which can be beneficial in managing autoimmune diseases and transplant rejections.

InChI:InChI=1/C10H15NO2/c12-11(13)10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2

Upstream product

• 281-23-2 adamantane 
• 64-19-7 acetic acid 
• 100-47-0 benzonitrile 
• 75-05-8 acetonitrile 
• 21245-43-2 tert-butyl (3r,5r,7r)-adamantane-1-carboperoxoate 
• 768-94-5 1-Adamantanamine 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 32314-61-7 1-nitroxyadamantane 

Downstream Products

• 768-95-6 1-adamanthanol 
• 32314-61-7 1-nitroxyadamantane 
• 107-46-0 Hexamethyldisiloxane 
• 768-93-4 1-iodoadamantane 
• 665-66-7 amantadine hydrochloride 
• 33187-62-1 (3s,5s,7s)-N-phenyladamantan-1-amine 
• 22734-10-7 1-Nitrosoadamantane 
• 53488-28-1 dinitrate of 1,3-adamantanediol 
• 55100-59-9 1,3-dinitroadamantane 
• 94238-10-5 3-nitroadamantan-1-yl nitrate 
• 768-94-5 1-Adamantanamine 
• 31463-23-7 N-adamantylhydroxylamine 

Relevant academic research and scientific papers

Chemoselectivity of Nitroxylation of Cage Hydrocarbons

Abstract: The composition of reaction mixtures obtained by nitroxylation of 13 cage hydrocarbons with 100% nitric acid and its mixtures with acetic acid, acetic anhydride, and methylene chloride has been studied. More reactive substrates react with lowest

Selective Phthalimido-N-oxyl (PINO)-Catalyzed C-H Cyanation of Adamantane Derivatives

We present a new method for the selective C(sp 3)-H cyanation of adamantane derivatives with PINO as the hydrogen abstracting reagent. A cyano radical is thereby transferred from p - toluenesulfonyl cyanide, allowing the cyanation of adamantane derivatives in up to 71% yield. The protocol presents a novel way to orthogonally functionalized adamantanes that are otherwise difficult to prepare. Mechanistic studies support the hypothesis of a radical pathway.

Aerobic oxidations with N-hydroxyphthalimide in trifluoroacetic acid

The potential of highly polar trifluoroacetic acid as a media for the metal-free aerobic oxidations propagated by phthalimide N-oxyl- (PINO) radical was demonstrated experimentally utilizing N-hydroxyphthalimide (NHPI) as a catalyst and HNO3 or NaNO2 as promoters. The oxidations of toluene, cyclohexane, adamantane, diamantane, and 3-oxadiamantane gave, respectively, benzaldehyde, adipic acid, 1-hydroxyadamantane, 1-hydroxydiamantane, and 9-hydroxy-3-oxadiamantane with up to 90% selectivities under high conversions of starting material. From the density functional theory computations at the M06-2X and B3LYP-D3 levels the polarized transition structures (TS) for the hydrogen abstraction from toluene and benzyl alcohol with highly electrophilic PINO-radical are substantially stabilized by non-covalent interactions (π–π stacking). Such additional stabilization is not present in the TS for the H-abstraction from benzaldehyde thus retarding its over-oxidation to benzoic acid.

One-pot synthesis of cage alcohols

An efficient one-pot procedure has been developed for the synthesis of cage alcohols with hydroxy groups in the bridgehead positions. The procedure includes initial nitroxylation with nitric acid or a mixture of nitric acid with acetic acid and subsequent hydrolysis in the presence of urea.

The synthesis and evaluation of new α-hydrogen nitroxides for 'living' free radical polymerization

Three N-alkoxyamines were synthesized for use in nitroxide-mediated radical polymerization. Upon thermolysis, they generate new acyclic α-hydrogen nitroxides: one adamantyl substituted and two diol-containing nitroxides. The initiators were tested in polymerization reactions in direct comparison with the initiator derived from the nitroxide TIPNO. Georg Thieme Verlag Stuttgart.

Nitration of alkanes with nitric acid by vanadium-substituted polyoxometalates

The nitration of alkanes by using nitric acid as a nitrating agent in acetic acid was efficiently promoted by vanadium-substituted Keggin-type phosphomolybdates such as [H4PVMo11O40], [H5PV2Mo10O40], and [H 6PV3Mo9O40] as catalyst precursors. A variety of alkanes including alkylbenzenes were nitrated to the corresponding nitroalkanes as major products in moderate yields with formation of oxygenated products under mild reaction conditions. The carbon-carbon bond cleavage reactions hardly proceeded. ESR, NMR, and IR spectroscopic data show that the vanadium-substituted polyoxometalate, for example, [H4PVMo 11O40], decomposes to form free vanadium species and [PMo12O40]3- Keggin anion. The reaction mechanism involving a radical-chain path is proposed. The polyoxometalates initially abstract the hydrogen of the alkane to form the alkyl radical and the reduced polyoxometalates. The reduced polyoxometalates subsequently react with nitric acid to produce the oxidized form and nitrogen dioxide. This step would be promoted mainly by the phosphomolybdates, [PMo12O 40]n-, and the vanadium cations efficiently enhance the activity. The nitrogen dioxide promotes the further formation of nitrogen dioxide and an alkyl radical. The alkyl radical is trapped by nitrogen dioxide to form the corresponding nitroalkane.

[VO(H2O)5]H[PMo12O40]- catalyzed nitration of alkanes with nitric acid

[VO(H2O)5]H[PMo12O40], which contains vanadyl counter cations and PMo12O40 3-, can act as a catalyst for the nitration of various alkanes including alkylbenzenes using nitric acid as a nitrating agent in acetic acid at 356 K.

Nitration of alkanes with nitric acid catalyzed by N-hydroxyphthalimide

Catalytic nitration of alkanes with nitric acid was first successfully achieved by the use of N-hydroxyphthalimide (NHPI) under mild conditions; the key to the present nitration was found to be the in situ generation of NO2 and phthalimide N-ox

NITRATION OR CARBOXYLATION CATALYSTS

In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the following formula (1): ???wherein R1and R2represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group and a cycloalkyl group, and R1and R2may bond together to form a double bond, or an aromatic or non-aromatic ring, and Y is an O or OH, and n denotes 1 to 3;, a substrate is allowed to contact with at least one reactant selected from (i) a nitrogen oxide and (ii) a mixture of carbon monoxide and oxygen to be introduced with at least one functional group selected from a nitro group and a carboxyl group. The nitrogen oxide includes, for example, a compound represented by the formula NxOy(e.g., N2O3, NO2). The substrate includes, for example, a compound having a methine carbon atom (e.g., adamantane), a compound having a methyl group or a methylene group at an adjacent moiety of an aromatic ring. According to such reaction, the substrate can be efficiently nitrated or carboxylated even in a mild or moderate condition.

Reactions of 1- and 2-Adamantyl Radicals with Nitrogen Dioxide

1- and 2-Adamantyl radicals similarly react with excess nitrogen dioxide to form respectively 1-nitro and 1-nitroxyadamane, 2-nitro and 2-nitroxyadamane, which are further nitrated to 1,3-dinitroadamantane, 1-nitro-3-nitroxyadamantane, 1,4-dinitroadamantane, and 1-nitro-4-nitroxyadamantane.