18674-50-5

Usage

Uses

Used in Pharmaceutical Industry:
()-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one oxime is used as a potential medicinal agent for its antimicrobial, antioxidant, and anti-inflammatory properties. It is being studied for its potential applications in the development of new drugs, particularly for treating infections and inflammatory conditions.
Used in Food Industry:
()-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one oxime is used as a flavoring agent in the food industry, capitalizing on its unique properties derived from carvone. It can enhance the taste and aroma of various food products, contributing to a more enjoyable consumer experience.
Used in Organic Chemistry:
()-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one oxime is used as a key intermediate in the synthesis of various organic compounds. Its importance in organic chemistry lies in its ability to contribute to the development of new chemical entities and materials with diverse applications.

Upstream product

• 76-22-2 Camphor 
• 7519-74-6 (+/-)-thiocampher 

Downstream Products

• 15340-92-8 Iso-α-campholenonitrile 
• 15373-31-6 α-campholenonitrile 
• 2437-76-5 2-bromo-p-cymene 
• 31180-79-7 (±)-camphor nitrimine 
• 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 
• 76-22-2 Camphor 
• 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 

Relevant academic research and scientific papers

Photoinduced, Copper-Catalyzed Three-Component Annulation of gem-Dialkylthio Enynes

Photoinduced, copper-catalyzed three-component radical annulation of gem-dialkylthio enynes, cyclobutanone oxime esters, and boronic acids was achieved, forming highly functionalized aryl thienyl sulfides with both good chemo- and diastereoselectivities. The reaction proceeds through a domino sequence involving cyanoalkyl radical-mediated intramolecular annulation of gem-dialkylthio enyne, alkenyl radical-promoted C(sp3)-S bond cleavage, and sulfur-centered radical-trapped Cu(II)-facilitated C-S cross-coupling. The protocol features simultaneous establishment of cyanoalkyl, cyclopentanone, and thiophene moieties and a thioether C-S bond in one pot with broad substrate scopes and versatile functional group tolerance under mild conditions.

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.

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.

Action of N-bromosuccinimide-dimethyl sulphoxide on camphor and its oxime derivative

Reaction of N-bromosuccinimide-dimethyl sulphoxide (NBS/DMSO) has been carried out on cyclic monoterpenoid taking camphor and its 2-keto oxime derivative as the starting material. The compounds obtained as a result of the reaction have been characterized and identified by spectroscopic analysis (IR, NMR) and by mass spectral data.

Silicon-catalyzed conversion of nitro compounds into ketones and poly(1,3-diketones)

The reaction of various secondary nitro compounds with 1.1 equivalents of potassium hydride in 1,4-dioxane and then with 0.10 equivalent of chlorotrimethylsilane gave the corresponding ketones in 62-90% yields. By a similar strategy, poly(1,3-diketones) were synthesized directly from nitroalkenes with sodium ethoxide, potassium hydride, and chlorotrimethylsilane in 1,4-dioxane. The use of chlorotrimethylsilane in a catalytic amount was the key to the success of this transformation; the use of an excess of chlorotrimethylsilane led to poor yields for the same reactions. Georg Thieme Verlag Stuttgart.

Camphor/Longicamphor and 7β-Formylnorlongifolane/7β-Acetylnorlongifolane Oximes: A Comparative Beckmann Rearrangement Study

Camphor oxime (3)/longicamphor oxime (4) have been shown to undergo Beckmann fragmentation on exposure to tosyl chloride in pyridine generating olefinic nitriles: 3->5+6 and 4->7+8+9; in the case of 4 this reaction provides an entry into the bicyclononane system characteristic of the secolongifolene diol fungal metabolite (10). 7β-Formylnorlongifolane oxime (14)/7β-acetylnorlongifolane oxime (15) when treated with the same Beckmann catalyst under similar conditions, afford the nitrile (16)/amide (17); on hydrolysis with base 17 gives the amine 18.Reaction of longicamphor (2) with hydroxylamine-O-sulfonic acid, however, a ffords the nitrogen-insertion product, α-longicamphidone (24) besides the fragmented nitrile (7).

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.