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Usage

Uses

Used in Organic Synthesis:
(1R,2R,4R)-2-AZIDO-1-ISOPROPYL-4-METHYLCYCLOHEXANE serves as a crucial precursor in organic synthesis, facilitating the preparation of a variety of compounds. These compounds hold potential applications in multiple domains, including pharmaceuticals and industry, due to their unique structural properties and reactivity.
Used in Chemical Research:
As a chiral molecule, (1R,2R,4R)-2-AZIDO-1-ISOPROPYL-4-METHYLCYCLOHEXANE is utilized in chemical research to explore the effects of stereochemistry on chemical reactions and the properties of resulting compounds. Its presence allows for the investigation of asymmetric synthesis and the development of enantioselective processes.
Used in Click Chemistry:
The azido group in (1R,2R,4R)-2-AZIDO-1-ISOPROPYL-4-METHYLCYCLOHEXANE makes it particularly useful in click chemistry. This set of reactions is highly efficient and modular, making it widely applicable in bioconjugation and materials science. (1R,2R,4R)-2-AZIDO-1-ISOPROPYL-4-METHYLCYCLOHEXANE's role in click chemistry enables the rapid and selective formation of new bonds, which is invaluable for creating complex molecular structures and materials with specific functions.
Used in Bioconjugation:
(1R,2R,4R)-2-AZIDO-1-ISOPROPYL-4-METHYLCYCLOHEXANE is applied in bioconjugation to attach biologically relevant molecules, such as proteins or nucleic acids, to other molecules or surfaces. (1R,2R,4R)-2-AZIDO-1-ISOPROPYL-4-METHYLCYCLOHEXANE's reactivity in click chemistry reactions allows for the efficient and specific formation of these conjugates, which is essential in various biotechnological and pharmaceutical applications.
Used in Materials Science:
In the field of materials science, (1R,2R,4R)-2-AZIDO-1-ISOPROPYL-4-METHYLCYCLOHEXANE contributes to the development of new materials with tailored properties. Its use in click chemistry facilitates the creation of sophisticated material architectures, such as polymers, dendrimers, and self-assembled structures, which can be applied in areas like nanotechnology, drug delivery, and diagnostics.

Upstream product

• 2230-82-2 menthyl tosylate 
• 959925-33-8 (1S,2R,5S)-2-i-propyl-5-methylcyclohexyl 4-methylbenzenesulfonate 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 61548-81-0 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate 
• 68-12-2 N,N-dimethyl-formamide 
• 89036-22-6 L-menthyl chloromethanesulphonate 
• 2216-51-5 (-)-menthol 
• 2216-52-6 Neomenthol 
• 13371-12-5 neomenthyl chloride 
• 15356-70-4 menthol 
• 61548-81-0 2‐isopropyl‐5‐methylcyclohexyl methanesulfonate 
• 117800-93-8 l-menthyl 8-quinolinesulfonate 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 21411-81-4 2-isopropyl-5-methyl-cyclohexylamine 

Downstream Products

• 34048-58-3 N-((1S)-neomenthyl)-formamide 

Relevant academic research and scientific papers

Enantiopure encaged Verkade's superbases: Synthesis, chiroptical properties, and use as chiral derivatizing agent

Verkade's superbases, entrapped in the cavity of enantiopure hemicryptophane cages, have been synthesized with enantiomeric excess (ee) superior to 98%. Their absolute configuration has been determined by using electronic circular dichroism (ECD) spectros

N-Heterocyclic Carbene Iron(III) Porphyrin-Catalyzed Intramolecular C(sp3)–H Amination of Alkyl Azides

Metal-catalyzed intramolecular C?H amination of alkyl azides constitutes an appealing approach to alicyclic amines; challenges remain in broadening substrate scope, enhancing regioselectivity, and applying the method to natural product synthesis. Herein we report an iron(III) porphyrin bearing axial N-heterocyclic carbene ligands which catalyzes the intramolecular C(sp3)–H amination of a wide variety of alkyl azides under microwave-assisted and thermal conditions, resulting in selective amination of tertiary, benzylic, allylic, secondary, and primary C?H bonds with up to 95 % yield. 14 out of 17 substrates were cyclized selectively at C4 to give pyrrolidines. The regioselectivity at C4 or C5 could be tuned by modifying the reactivity of the C5–H bond. Mechanistic studies revealed a concerted or a fast re-bound mechanism for the amination reaction. The reaction has been applied to the syntheses of tropane, nicotine, cis-octahydroindole, and leelamine derivatives.

Triiodide-Mediated δ-Amination of Secondary C?H Bonds

The Cδ?H amination of unactivated, secondary C?H bonds to form a broad range of functionalized pyrrolidines has been developed by a triiodide (I3?)-mediated strategy. By in situ 1) oxidation of sodium iodide and 2) sequestration of the transiently generated iodine (I2) as I3?, this approach precludes undesired I2-mediated decomposition which can otherwise limit synthetic utility to only weak C(sp3)?H bonds. The mechanism of this triiodide-mediated cyclization of unbiased, secondary C(sp3)?H bonds, by either thermal or photolytic initiation, is supported by NMR and UV/Vis data, as well as intercepted intermediates.

Synthesis and in vitro antibacterial evaluation of novel 4-substituted 1-menthyl-1,2,3-triazoles

Menthyl 1,4-disubstituted 1,2,3-triazole derivatives of hydroxybenzaldehydes, phenols and bile acids were synthesized via click chemistry. The novel synthesized compounds were evaluated for their in vitro antibacterial activity against Enterococcus faeciu

Enantioselective Rhodium(I)-Catalyzed Additions of Arylboronic Acids to N-1,2,3-Triazole-Isatin Derivatives: Accessing N-(1,2,3-Triazolmethyl)-3-hydroxy-3-aryloxindoles

Oxindoles and triazoles are very privileged frameworks in medicinal chemistry, and thus for the first time we report a catalytic asymmetric route that affords hitherto unknown families of N-(1,2,3-triazolmethyl)-3-hydroxy-3-phenyloxindoles using cheap bio

Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

Treatment of diarylphosphinous acid-borane amides possessing chiral amido functionality with an alkali metal solution in liquid ammonia induced a preferential dearomatization of one aryl substituent at phosphorus leading to the formation of non-equimolar amounts of diastereomers. Diastereoselectivity of dearomatization depends strongly on the structure of a chiral auxiliary.

Synthesis and structures of (-) menthyl and (+) neomenthyl substituted enantio pure bis(1,2,3-triazol-5-ylidene)PdI2 complexes and PEPPSI type (1,2,3-triazol-5-ylidene) (pyridine)PdI2complexes. Comparison of catalytic activities for C-C coupling

(-) Menthol was converted to 1-menthyl-3-methyl-4-phenyltriazolium iodide and 1-neomethyl-3-methyl-4-phenyltriazolium iodide in four steps. These triazolium salts that are enantio pure but diastereo isomers, served as precursors for the synthesis of the corresponding enantio pure bis(1,2,3-triazol-5-ylidene)PdI2 complexes with menthyl and neomenthyl wing tip groups. The palladium complexes were synthesized in high yields using a recently developed mild method under base free and silver free conditions at ambient temperature. These triazolium salts also served as precursors for the synthesis of the corresponding enantio pure PEPPSI type (1,2,3-triazol-5-ylidene) (pyridine)PdI2 complexes. All the complexes were thoroughly characterized by spectroscopic and single crystal XRD data. The relative catalytic activities of these complexes were compared for Suzuki-Miyaura C-C coupling.

Studies on synthesis of novel triazolalkyl tagged trifluoromethyl substituted pyrimidine derivatives and their evaluation for cytotoxic activity

The 2-amino-6-trifluoromethyl-3H-pyrimidin-4-one 1 was propargylated to give two regioisomers 2, 3 in definite proportions. Both regioisomers 2 and 3 were independently reacted with alkyl, aryl or cycloalkyl substituted azides under Sharpless conditions a

Practical synthesis of optically pure menthylamines starting from racemic neomenthol

A reliable and scalable route to racemic and highly enantiomerically enriched menthylamines exploits the technical product rac-neomenthol as the starting material. The elaborated protocol is based on nucleophilic substitution of the hydroxy moiety by azide. Subsequent reduction and resolution with tartaric acid provides the desired optically enriched menthylamines.

Stereoretentive halogenations and azidations with titanium(IV) enabled by chelating leaving groups

Titaniumdoes it again! With the help of nucleophile-assisting leaving groups (NALGs), alkyl bromides, iodides, and, for the first time, azides are obtained from sulfonates withcomplete retention of configuration. Critical to the design of these new titanium(IV) reactions has been the use of NALGs which are thought to chelate the Lewis acid reagent in the transition state promoting an SNi-type mechanism. (Chemical Equation Presented)