702-81-8

Usage

Uses

Used in Organic Synthesis:
3-Methyl-1-adamantanol is used as a building block for the synthesis of various organic compounds due to its unique molecular structure. It serves as a key intermediate in the production of a wide range of chemical products, contributing to the development of new materials and compounds with diverse applications.
Used in Pharmaceutical Industry:
3-Methyl-1-adamantanol is used as a key intermediate in the synthesis of pharmaceuticals. Its unique molecular structure allows for the development of new drugs with potential therapeutic benefits. 3-Methyl-1-adamantanol's stability and high boiling point make it suitable for use in various chemical processes involved in drug production.

Upstream product

• 770-14-9 3,7-dimethylenebicyclo[3.3.1]nonane 
• 702-98-7 2-methyladamantan-2-ol 
• 702-77-2 1-bromo-3-methyladamantane 
• 5202-50-6 1-hydroxy-3-iodomethyladamantane 
• 768-91-2 1-methyl-adamantane 
• 58201-66-4 (bromodifluormethyl)triphenylphosphonium bromide 
• 59039-27-9 3-Methyl-7-methylenbicyclo<3.3.1>non-2-en 
• 35356-98-0 3,7-Dimethyl-bicyclo<3.3.1>nona-2,7-dien 
• 84868-11-1 p-Toluolsulfonsaeure-(3-methyl-1-adamantyl)ester 
• 17768-37-5 acetate de methyl-3 adamantyl-1 
• 108-24-7 acetic anhydride 
• 101905-73-1 3,7-Dimethyl-bicyclo[3.3.1]nona-2,7-diene 
• 101974-65-6 3-methyl-1-adamantanol nitrate 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 702-77-2 1-bromo-3-methyladamantane 
• 14202-13-2 (3-methyladamantan-1-yl)acetic acid 
• 33649-73-9 1-Methyladamantane-3-carboxylic acid 
• 778-09-6 1-acetamido-3-methyltricyclo[3.3.1.1^3,7]decane 
• 78056-28-7 3-methyl-1-aminoadamantane 

Relevant academic research and scientific papers

Synthesis and biological evaluation of memantine nitrates as a potential treatment for neurodegenerative diseases

A series of memantine nitrate derivatives, as dual functional compounds with neuroprotective and vasodilatory activity for neurodegenerative diseases, was designed and synthesized. These compounds combined the memantine skeleton and a nitrate moiety, and thus inhibited the N-methyl-d-aspartic acid receptor and released NO in the central nervous system. The biological evaluation results revealed that the new memantine nitrates were effective in protecting neurons against glutamate-induced injury in vitro. Moreover, memantine nitrates dilated aortic rings against phenylephrine-induced contraction. The structure-activity relationships of neuroprotection and vasodilation were both analyzed. In further studies, compound MN-05 significantly protected cortical neurons by inhibiting Ca2+ influx, reducing free radical production and maintaining the mitochondrial membrane potential. Further research on MN-05 is warranted.

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.

Synthesis of hydroxy derivatives from adamantanecarboxylic acids in the system MnO2–H2SO4

A convenient procedure has been developed for the synthesis of mono- and dihydric cage alcohols from adamantanecarboxylic acids and their esters using the MnO2–H2SO4system. The reaction at elevated temperature involved both decarboxylation and decarbonylation of the initial acid or ester.

Efficient oxidation of adamantanes by sodium nitrite with molecular oxygen in trifluoroacetic acid

Oxidation of adamantanes by oxygen was effectively achieved by use of sodium nitrite as a catalyst in trifluoroacetic acid (TFA) to give 1-adamantyl trifluoroacetates, from which adamantanols were obtained in good yields. A catalytic amount of sodium nitrite was essential and TFA was the best solvent among solvents examined for this oxidation. Georg Thieme Verlag Stuttgart.

Formation of adamantan-1-ols by the reactions of adamantanes with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in trifluoromethanesulfonic acid

Adamantanes were treated with DDQ in trifluoromethanesulfonic acid followed by hydrolysis to give adamantan-1-ols in good yields.

Phosphorylation of Adamantane and its Derivatives in Trifluoroacetic Acid Medium

The possibility of dichlorophosphorylation of the carcass compounds of the adamantane series and of aryl(alkyl)carbinols, with phosphorus trichloride in the low-nucleophilicity trifluoroacetic acid medium was first demonstrated. A new preparative method for introducing a POCl2 group into the bridgehead and bridge positions of the adamantane nucleus, as well as into the α position of the side chain was developed. Some intermediate adamantyl cations may undergo isometizations, among them skeleton ones. A mechanism of the phosphorylation was proposed.

REACTION OF ALCOHOLS WITH BROMINE

Framework hydrocarbons react with bromine in water to form tertiary alcohols.In the absence of moisture the various alcohols react with bromine by a nucleophilic substitution mechanism, forming alkyl bromides.

TRANSANNULAR IONIC HYDROGENATION, AND ACIDIC CYCLIZATION AND ISOMERIZATION REACTIONS OF 3,7-DIMETHYLENEBICYCLONONANE AND ITS DERIVATIVES

The ionic hydrogenation, isomerization, and cyclization reactions of 3,7-dimethylenebicyclononane and related compounds have been studied.Ionic hydrogenation of the exocyclic methylene ?-bond occurs via the formation of alkyladamantanes.Reaction of 3,7-dimethylenebicyclononane with a chiral reagent results in the formation of an asymmetric adamantane derivative with an enantiomeric purity similar to that of the starting diene.