2094-73-7

Basic information

• Product Name: Ethyl adamantane-1-carboxylate
• Synonyms: TRICYCLO[(3.3.1.1(3,7)]DECAN-1-CARBOXYLIC ACID ETHYL ESTER;AKOS BC-0667;1-ADAMANTANECARBOXYLIC ACID ETHYL ESTER;Ethyl tricyclo[3.3.1.13,7]decane-1-carboxylate;ETHYL ADAMANTANE-1-CARBOXYLATE;ETHYL 1-ADAMANTANECARBOXYLATE;Tricyclo[3.3.1.1(3,7)-]decane-1-carboxylic acid, ethyl ester;Adamantane-1-carboxylic acid ethyl ester
• CAS NO: 2094-73-7
• Molecular Formula: C₁₃H₂₀O₂
• Molecular Weight: 208.3
• EINECS: 218-253-2
• Product Categories: Adamantane derivatives;Organic acids;Adamantanes
• Mol File: 2094-73-7.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 90-91°C 1mm
• Flash Point: 90-91°C/1mm
• Appearance: /
• Density: 1.106 g/cm³
• Vapor Pressure: 0.0113mmHg at 25°C
• Refractive Index: 1.4890
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 2050027
• CAS DataBase Reference: Ethyl adamantane-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl adamantane-1-carboxylate(2094-73-7)
• EPA Substance Registry System: Ethyl adamantane-1-carboxylate(2094-73-7)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 2094-73-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl adamantane-1-carboxylate is used as an antiviral agent for its ability to inhibit viral replication and protect cells from viral infections. Its antiviral properties make it a promising candidate for the development of new drugs to combat various viral diseases.
Used in Drug Delivery Systems:
In the field of drug delivery, Ethyl adamantane-1-carboxylate can be utilized as a carrier or enhancer to improve the bioavailability and efficacy of other antiviral drugs. Its unique chemical structure allows for the development of novel drug delivery systems that can target specific cells or tissues, thereby increasing the therapeutic potential of antiviral treatments.
Used in Chemical Research:
Ethyl adamantane-1-carboxylate can also be employed in chemical research as a starting material for the synthesis of other adamantane derivatives with potential applications in various fields, such as materials science, pharmaceuticals, and agrochemicals. Its versatile chemical properties make it a valuable compound for the development of new molecules with specific functions and activities.

InChI:InChI=1/C13H20O2/c1-2-15-12(14)13-6-9-3-10(7-13)5-11(4-9)8-13/h9-11H,2-8H2,1H3

Upstream product

• 201230-82-2 carbon monoxide 
• 281-23-2 adamantane 
• 828-51-3 1-Adamantanecarboxylic acid 
• 75-03-6 ethyl iodide 
• 39487-54-2 1-((dimethylamino)(phenyl)methyl)naphthalen-2-ol 
• 17760-81-5 1-[2-oxo-2-(tricyclo[3.3.1.1^3,7]dec-1-yl)ethyl]pyridinium bromide 
• 19925-58-7 2-adamantan-1-yl-oxazole-4,5-dione; hydrochloride 
• 74-96-4 ethyl bromide 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 60-29-7 diethyl ether 
• 78-39-7 Triethyl orthoacetate 
• 64-17-5 ethanol 
• 770-71-8 1-adamantanemethanol 
• 65012-54-6 1-adamantanecarboxylate anion 

Downstream Products

• 180258-71-3 2-(1-adamantyl)pyrroline 
• 3796-79-0 N-phenyl-1-adamantanecarboxamide 
• 111079-75-5 1-adamantyl dichloromethyl ketone 
• 768-95-6 1-adamanthanol 
• 23074-42-2 1-adamantanecarbonitrile 
• 23938-42-3 3-((3r,5r,7r)-adamantan-1-yl)-3-oxopropanenitrile 
• 1338815-28-3 3-(adamantan-1-yl)-1-p-tolyl-1H-pyrazol-5-amine 
• 17774-98-0 Adamantan-1-carbonsaeure-N²-p-tosylhydrazid 

Relevant articles and documents

An effective formylation of adamantane with CO initiated by the aprotic organic superacid CBr4·2AlBr3 under mild conditions

The reaction of adamantane with carbon monoxide at -45°/+20°C over 0.5-2 h, catalyzed by the aprotic organic superacid CBr4·2AlBr3, is described. The formylation of adamantane under CO atmosphere at 0/+20°C in the presence of methylcyclopentane as a source of hydride ion affords 1-adamantanecarbaldehyde (1) in yield 70-72% on adamantane for 1 h.

Synthesis and study of properties of azoles and their derivatives - Communication 22. Syntheses based on 1-adamantanecarbonitrile

1. 1-Adamantanecarbonitrile reacts with alcohols and hydrogen chloride with greater difficulty than do aliphatic nitriles to give the hydrochlorides of the imino esters of 1-adamantanecarboxylic acid, which are more stable than the corresponding compounds of the aliphatic series. 2. The hydrochloride of the methyl imino ester of 1-adamantanecarboxylic acid condenses with ethylenediamine, o-phenylenediamine and o-aminophenol in the usual manner to give the corresponding heterocyclic compounds. 3. The methyl imino ester of 1-adamantanecarboxylic acid when heated with ethanolamine gives the corresponding oxazoline. The hydrochloride of the methyl imino ester of 1-adamantanecarboxylic acid does not give the s-triazine when heated, and instead gives 1-adamantanecarbonitrile.

Oxidation of Deactivated Cage Substrates in the System H2SO4–HNO3

Abstract: The kinetics of oxidation of 16 carboxylic acid esters of the adamantaneseries in the systemH2SO4–HNO3have been studied, and the effective rate constants have been determined. Thereaction is described by the pseudo-first-order kinetic equation. The primarykinetic isotope effect has been estimated at 2.9±0.3. The rate-determining stepof the oxidation process is cleavage of the adamantane C–H bond. The presence ofan ethyl group at the bridgehead position increases the reactivity of adamantanesubstrates toward oxidation, whereas methyl, ethoxycarbonyl, andethoxycarbonylmethyl groups reduce the reactivity.

Design, Synthesis, and in vitro Evaluation of P2X7 Antagonists

The P2X7 receptor is a promising target for the treatment of various diseases due to its significant role in inflammation and immune cell signaling. This work describes the design, synthesis, and in vitro evaluation of a series of novel derivatives bearing diverse scaffolds as potent P2X7 antagonists. Our approach was based on structural modifications of reported (adamantan-1-yl)methylbenzamides able to inhibit the receptor activation. The adamantane moieties and the amide bond were replaced, and the replacements were evaluated by a ligand-based pharmacophore model. The antagonistic potency of the synthesized analogues was assessed by two-electrode voltage clamp experiments, using Xenopus laevis oocytes that express the human P2X7 receptor. SAR studies suggested that the replacement of the adamantane ring by an aryl-cyclohexyl moiety afforded the most potent antagonists against the activation of the P2X7 cation channel, with analogue 2-chloro-N-[1-(3-(nitrooxymethyl)phenyl)cyclohexyl)methyl]benzamide (56) exhibiting the best potency with an IC50 value of 0.39 μΜ.

One-pot dichlorinative deamidation of primary β-ketoamides

An approach to the dichlorinative deamidation of primary β-ketoamides through ketonic cleavage is described, and a series of α,α-dichloroketones were furnished mostly in the presence of TEMPO. Based on control experiments, a mechanism involving tandem dichlorination and deamidation is proposed to interpret the observed reactivity.

One-pot transformation of carboxylic acids into nitriles

A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. This method is useful for the conversion of various aromatic and aliphatic carboxylic acids into the corresponding nitriles in a one-pot procedure. A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. Copyright

Reactions of O-quinone methides with pyridinium methylides: A diastereoselective synthesis of 1,2-dihydronaphtho[2,1- b ]furans and 2,3-dihydrobenzofurans

A simple, general route to the 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans substituted at C-2 by an acyl or aryl group, starting from phenolic Mannich bases and pyridinium ylides, has been developed. The mechanism of the reaction is believed to involve the formation of the o-quinone methide intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecular nucleophilic substitution.

Preparation of 1-adamantyl ketones: Structure, mechanism of formation and biological activity of potential by-products

Reactions between adamantane-1-carbonyl chloride and several Grignard reagents as well as interactions with solvents have been examined. Some new and unexpected adamantane derivatives were isolated, fully characterized and their biological activity determined. In particular, an unexpected isochromanone 16 was formed in an SEAr process, in which a stable hydrocarbon was the leaving group.

Efficient esterification of carboxylic acids and phosphonic acids with trialkyl orthoacetate in ionic liquid

An operationally simple, inexpensive, efficient, and environmentally friendly esterification of various carboxylic acids, phosphonic acids, and phosphinic acids with triethyl orthoacetate or trimethyl orthoacetate under neutral conditions in a typical room temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate, was successfully carried out to provide the corresponding ethyl esters or methyl esters in high yields.

Influence of catalytic system composition on formation of adamantane containing ketones

The preparation of non-symmetrical ketones by the reaction of acyl chlorides and the corresponding Grignard reagents in the presence of catalytic amounts of metal halides is described. The composition of catalyst has a great influence on the yield of the required ketone as well as on side product formation. For each catalytic system, the yield of ketone and the number of side products changes with the time of addition of the Grignard reagent. We examined the influence of both factors in our model reaction of adamantane-1-carbonyl chloride with ethylmagnesium bromide and discussed the possible mechanisms from this point of view. We have found ZnCl2, MnCl2, AlCl 3 and CuCl to be active catalytic components and developed very efficient, cheap and fast methods for the preparation of alkyl adamantyl ketones. The procedure was also tested for the synthesis of other alkyl aryl ketones. Graphical Abstract.