6240-11-5

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Adamantaneethanol is used as a synthetic building block for the development of novel pharmaceutical compounds. Its rigid and symmetrical structure allows for the creation of complex molecules with potential therapeutic applications.
2. Used in Chemical Synthesis:
1-Adamantaneethanol is used as a key intermediate in the synthesis of various organic compounds, such as 4-(adamant-1-ylethylenoxycarbonyl)phthalanhydride and poly(2-methoxy-5-cyclohexylmethyloxy-p-phenylene vinylene)adamantine-containing phthalocyanines. These compounds have potential applications in areas like materials science, optoelectronics, and sensing technologies.
3. Used in Research and Development:
1-Adamantaneethanol serves as a valuable research tool for chemists and material scientists. Its unique structural properties make it an interesting candidate for studying the effects of molecular architecture on the properties and performance of synthesized materials.

InChI:InChI=1/C12H20O/c13-2-1-12-6-9-3-10(7-12)5-11(4-9)8-12/h9-11,13H,1-8H2

Upstream product

• 51849-10-6 1-adamantane methyl iodide 
• 27174-71-6 methyl 2-(adamantan-1-yl)acetate 
• 29817-45-6 1-Adamanthylethyl acetate 
• 4942-47-6 (adamant-1-yl)-acetic acid 

Downstream Products

• 26831-48-1 2-(adamantan-1-yl)ethyl-4-methylbenzenesulfonate 
• 139143-48-9 (S)-2-Benzyloxycarbonylamino-4-methyl-pentanoic acid 2-adamantan-1-yl-ethyl ester 
• 316377-87-4 2-(1-adamantyl)ethyl p-nitrobenzenesulfenate 
• 1159340-38-1 tert-butyl (2-{4-[(1R,S)-2-(1-adamantyl)ethoxy]phenyl}-1-methylethyl)carbamate 
• 828-51-3 1-Adamantanecarboxylic acid 
• 16269-16-2 3-(1-adamantyl)propanoic acid 
• 26482-53-1 2-(1-adamantyl)ethanamine 
• 107847-66-5 1-[(E)-3-phenylprop-2-en-1-yl]adamantane 

Relevant academic research and scientific papers

Me3SI-promoted chemoselective deacetylation: a general and mild protocol

A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.

Synthesis and Structure-Activity Relationships of Ring-Opened Bengamide Analogues against Methicillin-Resistant Staphylococcus aureus?

Methicillin-resistant Staphylococcus aureus (MRSA) has become a major threat on public health because of the increase of clinically isolated strains that exhibit resistance to many antibiotics. Therefore, development of new antibiotics for the treatment of MRSA infection is a sustained challenge. We have previously identified a ring-opened bengamide analogue L472-2 that displays moderate activity against the growth of S. aureus. In our previous work, we started from L472-2 and identified a class of analogues containing alkynyl groups which have the potential to activate SaClpP activity but moderate antibacterial activity. Herein, we focused on the antibacterial activity of L472-2, and a novel series of ring-opened bengamide analogues were synthesized and their activities were evaluated against MRSA. By conducting a compact analysis of the structure-activity relationships (SAR) of these analogues, we found that an adamantane ethanol ester bengamide 2j showed excellent antibacterial activity towards six S. aureus strains, including MRSA, while it does not activate ClpP. Therefore, these bengamide analogues represent a new class of candidates that suppress MRSA viability.

Drastic fluorine effect: Complete reversal of the selectivity in the Au-catalyzed hydroalkoxylation reaction of fluorinated haloalkynes

The gold-catalyzed hydration reaction of haloalkynes is highly regioselective producing 2-halomethylketones as the sole products. Herein, we document a drastic fluorine effect where the reaction of 1-halo-3,3-difluoroalkynes as substrates leads to a complete reversal of selectivity and produces 3,3-difluoroesters as the unique products.

MITOCHONDRIA-TARGETING PEPTIDES

Disclosed are analogs of SBT-20. The compounds are useful for the treatment and prevention of ischemia-reperfusion injury (e.g., cardiac ischemia-reperfusion injury) or myocardial infarction.

Pd-Catalyzed intermolecular C-H bond arylation reactions: Effect of bulkiness of carboxylate ligands

A bulky carboxylic acid bearing one 1-adamantylmethyl and two methyl substituents at the α-position is demonstrated to work as an efficient carboxylate ligand source in Pd-catalyzed intermolecular C(sp2)-H bond arylation reactions. The reactions proceeded smoothly under mild conditions, taking advantage of the steric bulk of the carboxylate ligands.

Binding study on 1-adamantylalkyl(benz)imidazolium salts to cyclodextrins and cucurbit[n]urils

Multitopic guests are used as key components of molecular triggers, switchers, sensors, or reactors in recent supramolecular chemistry studies. The increasing complexity of these compounds correlates with the need for versatile, synthetically available binding motifs (building blocks) with tuneable supramolecular properties. The utilisation of a favoured 1-adamantylmethyl moiety in ammonium, imidazolium and pyridinium salts is sometimes restricted by synthetic difficulties most likely related to the adamantane cage bulkiness. Therefore, we prepared a series of new adamantylated (benz)imidazolium salts with longer flexible linkers between the adamantane cage and cationic moiety. We tested the supramolecular properties of these binding motifs towards the natural cyclodextrins α-CD, β-CD and γ-CD and cucurbit[n]urils (n= 7, 8) using NMR, mass spectrometry and titration calorimetry. All tested guests formed 1:1 complexes with the abovementioned hosts, retaining binding strengths, selectivity, and complex geometries in comparison to the parent methylene-linked homologues. We did not confirm our original concern that longer linkers would negatively affect the binding strength towards CBns due to the reduction in the ion-dipole interaction contribution. Therefore, we believe that adamantylalkyl imidazolium binding motifs can be used for multitopic supramolecular guest construction.

Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes

The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

Bridged bicyclic 2,3-dioxabicyclo[3.3.1]nonanes as antiplasmodial agents: Synthesis, structure-activity relationships and studies on their biomimetic reaction with Fe(II)

Despite recent advancements in its control, malaria is still a deadly parasitic disease killing millions of people each year. Progresses in combating the infection have been made by using the so-called artemisinin combination therapies (ACTs). Natural and synthetic peroxides are an important class of antimalarials. Here we describe a new series of peroxides synthesized through a new elaboration of the scaffold of bicyclic-fused/bridged synthetic endoperoxides previously developed by us. These peroxides are produced by a straightforward synthetic protocol and are characterized by submicromolar potency when tested against both chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains. To investigate their mode of action, the biomimetic reaction of the representative compound 6w with Fe(II) was studied by EPR and the reaction products were characterized by NMR. Rationalization of the observed structure-activity relationship studies was performed by molecular docking. Taken together, our data robustly support the hypothesized mode of activation of peroxides 6a-cc and led to the definition of the key structural requirements responsible for the antiplasmodial potency. These data will pave the way in future to the rational design of novel optimized antimalarials suitable for in vivo investigation.

Multiple Halogenation of Aliphatic C?H Bonds within the Hofmann–L?ffler Manifold

An innovative approach to position-selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeded within the Hofmann-L?ffler manifold with amidyl radicals as the sole mediators to induce selective 1,5- and 1,6-hydrogen-atom transfer followed by halogenation. Multiple halogenation events of up to four innate C?H bond functionalizations were accomplished. The broad applicability of this new entry into polyhalogenation and the resulting synthetic possibilities were demonstrated for a total of 27 different examples including mixed halogenations.

Preparative synthesis of vinyl diamondoids

We describe a convenient four-step preparation of 1-vinyl adamantane, 1-vinyl diamantane, and 4,9-divinyl diamantane from the respective diamondoid acetic acids in 50-80% isolated yields involving esterification, reduction, and hydrobromination/dehydrobromination. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.