36065-15-3

Usage

Uses

Used in Organic Synthesis:
(1S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime serves as a valuable intermediate in organic synthesis, contributing to the creation of various complex organic molecules. Its unique bicyclic structure and ketoxime functional groups provide opportunities for further chemical reactions and modifications, making it a useful building block in the synthesis of specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (1S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime is utilized as an intermediate in the development of new drugs. Its reactivity and stability make it suitable for the synthesis of pharmaceutical compounds, potentially leading to the discovery of novel therapeutic agents.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, this bicyclic ketoxime is employed as an intermediate for the synthesis of agrochemicals. Its properties allow it to be incorporated into the development of pesticides, herbicides, and other agricultural chemicals, contributing to more effective and targeted crop protection solutions.
Given the wide range of applications for ketoximes in general, it is likely that (1S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime can be found in various other industries as well, such as in the synthesis of fragrances, dyes, and other specialty chemicals. However, the specific uses would depend on the individual characteristics of (1S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime, including its reactivity, stability, and potential applications in different fields.

InChI:InChI=1/C10H17NO/c1-9(2)7-4-5-10(9,3)8(6-7)11-12/h7,12H,4-6H2,1-3H3/b11-8+/t7?,10-/m1/s1

Upstream product

• 464-48-2 (1S)-camphor 
• 76-22-2 Camphor 

Downstream Products

• 86362-64-3 (-)(1S:2R:4S)-N-cyclohexyl-1,7,7-trimethylbicyclo<2.2.1>hept-2-ylamine 
• 86362-64-3 (+)(1S:2S:4R)-N-cyclohexyl-1,7,7-trimethylbicyclo<2.2.1>hept-2-ylamine 
• 80985-40-6 (-)(1S:2R:4S)-N-cyclopentyl-1,7,7-trimethylbicyclo<2.2.1>hept-2-ylamine hydrochloride 
• 80985-40-6 (+)(1S:2S:4s)-N-cyclopentyl-1,7,7-trimethylbicyclo<2.2.1>hept-2-ylamine hydrochloride 
• 31180-79-7 camphor nitrimine 
• 28154-30-5 (1S,4S)-2-Chloro-1,7,7-trimethyl-2-nitro-bicyclo[2.2.1]heptane 
• 1152-98-3 C₁₇H₂₁NO₂ 
• 32511-34-5 (R)-Bornylamine 
• 2223-67-8 1,7,7-trimethylbicyclo[2.2.1]heptan-exo-2-amine 
• 6627-72-1 rac-endo-borneol 
• 464-48-2 (1S)-camphor 

Relevant academic research and scientific papers

2-((1-Phenyl-1H-1,2,3-triazol-4-yl)methyl)-2-azabicyclo[3.2.1]octan-3-one derivatives: Simplification and modification of aconitine scaffold for the discovery of novel anticancer agents

The molecular chaperone heat shock protein 90 (Hsp90) is a promising target for cancer therapy. Natural product aconitine is a potential Hsp90 inhibitor reported in our previous work. In this study, we designed and synthesized a series of 2-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-2-azabicyclo[3.2.1]octan-3-one derivatives as potent Hsp90 inhibitors by simplifying and modifying aconitine scaffold. Among these compounds, 14t exhibited an excellent antiproliferative activity against LoVo cells with an IC50 value of 0.02 μM and a significant Hsp90α inhibitory activity with an IC50 value of 0.71 nM. Molecular docking studies provided a rational binding model of 14t in complex with Hsp90α. The following cell cycle and apoptosis assays revealed that compound 14t could arrest cell cycle at G1/S phase and induce cell apoptosis via up-regulation of bax and cleaved-caspase 3 protein expressions while inhibiting the expressions of bcl-2. Moreover, 14t could inhibit cell migration in LoVo and SW620 cell lines. Consistent with in vitro results, 14t significantly repressed tumor growth in the SW620 xenograft mouse model.

Potential Synthetic Adaptogens: V. Synthesis of Cage Monoamines by the Schwenk–Papa Reaction

The reduction of cage ketoximes under Schwenk–Papa reaction conditions was studied to establish that the d,l, d- and l-camphor oximes are smoothly reduced to the corresponding amines in high yields. At the same time, d,l-norcamphor and adamantan-2-one oximes undergo partial catalytic deoximation to form a mixture of the corresponding amines and alcohols.

Synthesis and evaluation of camphor and cytisine-based cyanopyrrolidines as DPP-IV inhibitors for the treatment of type 2 diabetes mellitus

In this study, bornyl- and cytisine-based cyanopyrrolidines as potent dipeptidyl peptidase-IV (DPP-IV) inhibitors were synthesised. The in vitro inhibiting activities of bornyl- and cytisine derivatives towards DPP-IV were evaluated. Bornyl-based cyanopyrrolidines were shown to have moderate inhibitory activity with regard to DPP-IV (1.27–15.78 μM). A docking study was performed to elucidate the structure-activity relationship of the obtained compounds. The in vivo hypoglycemic activities of the same compounds were evaluated with the oral glucose tolerance test (OGTT) in mice. Bornyl-based cyanopyrrolidines were shown to have good hypoglycemic activity.

Ruthenium Trichloride Catalyzed Highly Efficient Deoximation of Oximes to the Carbonyl Compounds and Nitriles without Acceptors

An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields. An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields.

Fluorinative α-cleavage of cyclic ketoximes with diethylaminosulfur trifluoride: An efficient synthesis of fluorinated carbonitriles

Diethylaminosulfur trifluoride effects ready cleavage of cyclic ketoximes to fluorinated carbonitriles.

Stereochemical Assignment of Camphoroxime by PMR Spectroscopy Using Tris(dipivalomethanato)europium(III)

Stereochemistry of camphoroxime has been deciphered with the help of PMR spectroscopy using tris(dipivalomethanato)europium (III) as a shift reagent.The hydroxyl group in the oxime has been shown to be syn to γ-methyl on the basis of its anisotropic effect as well as the pronounced paramagnetic induced shift of the γ-methyl.Three methyl (α-, β- and γ-) resonances have also been rationalised using various concentrations of the shift reagent.