2111-71-9

Usage

Uses

Used in Organic Synthesis:
(E)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-hydroxymethanimine is used as a key intermediate in the synthesis of various organic compounds. Its unique bicyclic structure and functional groups make it a valuable building block for creating complex molecules with specific properties and applications.
Used as a Ligand in Coordination Chemistry:
In coordination chemistry, (E)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-hydroxymethanimine is used as a ligand to form coordination complexes with metal ions. These complexes can exhibit unique chemical and physical properties, which can be exploited in various applications, such as catalysis, sensing, and materials science.
Used in Medicinal Chemistry:
(E)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-hydroxymethanimine is used as a starting material or a structural component in the development of new pharmaceuticals. Its demonstrated anti-inflammatory and neuroprotective effects make it a promising candidate for the treatment of various diseases and conditions, including inflammation-related disorders and neurodegenerative diseases.
Used in Pharmaceutical Research and Development:
In the pharmaceutical industry, (E)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-hydroxymethanimine is used as a molecule of interest for further research and development. Its potential medicinal properties, along with its unique chemical structure, make it a valuable compound for exploring new therapeutic approaches and developing innovative drugs.

Upstream product

• 23727-16-4 myrtenal 
• 6712-78-3 myrtenol 
• 564-94-3 myrtenal 
• 564-94-3 (+/-)-(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde 
• 515-00-4 (+/-)-myrtenol 

Downstream Products

• 865768-83-8 (-)-(1S,2R,3S,5R)-3-diphenylphosphanyl-6,6-dimethylbicyclo[3.1.1]heptane-2-carbonitrile 
• 865769-20-6 (-)-(1R,5S)-N-[2-hydroxy-(1R)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide 
• 865769-22-8 (-)-(1R,5S)-N-[2-hydroxy-(1S)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide 
• 865769-28-4 (-)-2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-(4S)-phenyl-4,5-dihydro-1,3-oxazole 
• 865769-26-2 (+)-2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-4(R)-phenyl-4,5-dihydro-1,3-oxazole 

Relevant academic research and scientific papers

Ruthenium-catalyzed rearrangement of aldoximes to primary amides in water

The rearrangement of aldoximes to primary amides has been studied using the readily available arene-ruthenium(II) complex [RuCl2(η 6-C6Me6){P(NMe2)3}] (5 mol %) as catalyst. Reactions proceeded cleanly in pure water at 100 °C without the assistance of any cocatalyst, affording the desired amides in high yields (70-90%) after short reaction times (1-7 h). The process was operative with both aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldoximes and tolerated several functional groups. Reaction profiles and experiments using 18O-labeled water indicate that two different mechanisms are implicated in these transformations. In both of them, nitrile intermediates are initially formed by dehydration of the aldoximes. These intermediates are then hydrated to the corresponding amides by the action of a second molecule of aldoxime or water. A kinetic analysis of the rearrangement of benzaldoxime to benzamide is also discussed.

Syntheses of new chiral phosphane ligands by diastereoselective conjugate addition of phosphides to enantiomerically pure acceptor-substituted olefins from the chiral pool

A variety of new chiral phosphanes were prepared by highly diastereoselective additions of phosphanes to α,β-unsaturated carbonyl compounds and related acceptor-substituted olefins derived from myrtenal as ex chiral pool source. Monophosphanes with astereogenic as well as stereogenic phosphorus are described. In addition diphosphanes were prepared by a highly diastereoselective double conjugate addition of a secondary diphosphane. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.