59223-70-0

Usage

Uses

Used in Organic Synthesis:
3-Hydroxy-1-adamantanecarbonitrile is used as a building block in organic synthesis for the creation of various biologically active molecules. Its adamantine scaffold, hydroxyl, and nitrile groups provide a versatile platform for the development of new compounds with potential applications in various fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-Hydroxy-1-adamantanecarbonitrile is utilized as a key intermediate in the synthesis of drug candidates. Its unique structure allows for the exploration of novel chemical entities with potential therapeutic effects. 3-Hydroxy-1-adamantanecarbonitrile's reactivity and stability contribute to the design and optimization of new drugs with improved pharmacological properties.
Used in Drug Development:
3-Hydroxy-1-adamantanecarbonitrile plays a crucial role in drug development, serving as a starting material for the synthesis of potential therapeutic agents. Its presence in the molecular structure can influence the pharmacokinetics, pharmacodynamics, and overall efficacy of the resulting drug molecules. Researchers leverage the compound's properties to design drugs with enhanced selectivity, potency, and safety profiles.

Upstream product

• 21886-25-9 3-bromo-1-adamantanecarbonitrile 
• 23074-42-2 1-adamantanecarbonitrile 
• 59223-60-8 3-(p-Toluolsulfonyloxy)adamantan-1-carbonitril 
• 24569-89-9 1,3-dehydroadamantane 
• 506-77-4 cyanogen chloride 
• 60933-04-2 2,2,2-Trifluoro-ethanesulfonic acid 1-cyano-adamantan-2-yl ester 
• 21816-08-0 3-bromoadamantane-1-carboxylic acid 
• 768-95-6 1-adamanthanol 
• 19158-51-1 P-toluenesulfonyl cyanide 

Downstream Products

• 59223-60-8 3-(p-Toluolsulfonyloxy)adamantan-1-carbonitril 
• 420120-31-6 3-hydroxytricyclo[3.3.1.1³'⁷]decane-1-carbaldehyde 
• 58727-80-3 1-carbaldehyde-3-chloroadamantane 

Relevant academic research and scientific papers

Direct Oxidation of Csp3?H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow

A fast, scalable, and safer Csp3?H oxidation of activated and un-activated aliphatic chains can be enabled by methyl(trifluoromethyl)dioxirane (TFDO). The continuous flow platform allows the in situ generation of TFDO gas and its rapid reactivity toward tertiary and benzylic Csp3?H bonds. The process exhibits a broad scope and good functional group compatibility (28 examples, 8–99 %). The scalability of this methodology is demonstrated on 2.5 g scale oxidation of adamantane.

Photoinduced direct cyanation of C(sp3)-H bonds

A general and practical synthetic protocol for the direct transformation of unreactive C(sp3)-H bonds to C(sp3)-CN bonds has been developed. The homolytic cleavage of the C-H bond is initiated by photo-excited benzophenone, and the resulting carbon radical subsequently reacts with tosyl cyanide to afford the corresponding nitrile in a highly efficient manner. The present methodology is widely applicable to various starting materials including ethers, alcohols, amine derivatives, alkanes, and alkylbenzenes. This newly developed C-H cyanation protocol provides a powerful tool for selective one-carbon elongation for the construction of architecturally complex molecules. Georg Thieme Verlag Stuttgart - New York.

Photochemically induced radical transformation of C(sp3)-H bonds to C(sp3)-CN bonds

A general protocol for direct transformation of unreactive C(sp 3)-H bonds to C(sp3)-CN bonds has been developed. The C-H activation was effected by photoexcited benzophenone, and the generated carbon radical was subsequently trapped with tosyl cyanide to afford the corresponding nitrile in a highly efficient manner. The present methodology is widely applicable to versatile starting materials and, thus, serves as a powerful tool for selective one-carbon elongation for construction of architecturally complex molecules.

TETRACYCLO3,7.01,3>DECANE IN REACTIONS WITH SOME ACYL- AND CYANO-CONTAINING REAGENTS

The splitting of the strained ring in tetracyclo3,7.01,3>decane with some acyl- and cyano-containing electrophilic reagents (acetyl chloride, complexes of cyanogen chloride and acetyl cyanide with Lewis acids) goes with the formation of 1,3-addition products.

Fluorination of Adamantane Derivatives with Oxygen Difluoride

Fluorination of adamantane and adamantane derivatives 1 with OF2 in the absence of an HF-trap gives fluoroadamantanes 2 and adamantanols 3 in varying amounts.Increasing yields of 2 are obtained in the presence of Na2CO3 as an HF-trap.In addition, the fluorooxahomoadamantanes 4b and e are formed in this reaction.The fluorination of adamantanone (5) with OF2 leads to analogous products.

Polar Effects. X. Polar Substituent Effects in the Solvolysis of 3-Substituted 1-Adamantyl Bromides and Tiluenesulfonates

The rate constants for 3-substituted adamantyl p-toluenesulfonated 3a-3k in ethanol/water 80:20 correlate well with the respective inductive subsitutent constants ?qI.The reaction constant ρ for the toluenesulfonates 3 is 10percent karger than for the corresponding bromides 2, indicating somewhat more charge separation in the activation of the toluenesulfonates.Evidence is presented that stabilization of the resultant 1-adamantyl cations by induction involves graded 1,3-bridging, which is favored when the subsituent is an electrofugal group, and that stabilization by n-electron donors involves C,C-hyperconjugation.Rate ratios for the toluenesulfonates 3 and the bromides 1 exceed 1E3 and are almost independent of the 3-subsituents.The implications of this are discussed in the light current hypotheses.

Herstellung und Solvolyse von 3-substituierten p-Toluolsulfonsaeure-(1-adamantyl)estern

Methods for the preparation of some hitherto unknown 3-substituted 1-adamantyl toluenesulfonates are evaluated.Their solvolysis products in dioxane/water 70:30 are reported.