56820-19-0

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 91, p. 3390, 1969 DOI: 10.1021/ja01040a061

Upstream product

• 55975-26-3 Ozonid des Cyclohexylidenadamantans 
• 45985-26-0 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl 
• 134329-63-8 4(a)-(trifluoromethylsulfonyloxy)adamantan-2-one 

Downstream Products

• 768-41-2 2-azatricyclo[3.3.1.13,7 ]decane 
• 19489-16-8 (1R,3r,5S)-bicyclo[3.3.1]nonane-3-carboxylic acid 
• 19489-17-9 3α-Methoxycarbonyl-1α(H),5α(H)-bicyclo<3.3.1>nonan 
• 66483-55-4 (+)-(1S,3R,5R)-endo-(3-bicyclo<3.3.1>non-6-enyl) methyl ketone 
• 1448697-71-9 3-(1H-benzotriazol-1-yl)-1-(5-hydroxy-2-azatricyclo[3.3.1.1^3,7]dec-2-yl)-3-phenylpropan-1-one 
• 1389264-13-4 methyl 2-azatricyclo[3.3.1.1³'⁷]decane-5-carboxylate 
• 3015-17-6 methyl 2-azatricyclo[3.3.1.1^3,7]decane hydrochloride 
• 1274919-03-7 N-benzyloxycarbonyl-endo-bicyclo[3.3.1]non-6-en-3-ylamide 

Relevant academic research and scientific papers

SUBSTITUTED-QUINOXALINE-TYPE BRIDGED-PIPERIDINE COMPOUNDS AND THE USES THEREOF

The invention relates to Substituted-Quinoxaline-Type Bridged-Piperidine Compounds, compositions comprising an effective amount of a Substituted-Quinoxaline- Type Bridged-Piperidine Compound and methods to treat or prevent a condition, such as pain, compr

Dispiro-1,2,4-trioxane analogues of a prototype dispiro-1,2,4-trioxolane: Mechanistic comparators for artemisinin in the context of reaction pathways with iron(II)

Single electron reduction of the 1,2,4-trioxane heterocycle of artemisinin (1) forms primary and secondary carbon-centered radicals. The complex structure of 1 does not lend itself to a satisfactory dissection of the electronic and steric effects that influence the formation and subsequent reaction of these carbon-centered free radicals. To help demarcate these effects, we characterized the reactions of achiral dispiro-1,2,4-trioxolane 4 and dispiro-1,2,4-trioxanes 5-7 with ferrous bromide and 4-oxo-TEMPO. Our results suggest a small preference for attack of Fe(II) on the nonketal peroxide oxygen atom of 1. For 4, but not for 5 and 6, there was a strong preference for attack of Fe(II) on the less hindered peroxide bond oxygen atom. The steric hindrance afforded by a spiroadamantane in a five-membered trioxolane is evidently much greater than that for a corresponding six-membered trioxane. Unlike 1, 5-7 fragment by entropically favored β-scission pathways forming relatively stable α-oxa carbon-centered radicals. These data suggest that formation of either primary or secondary carbon-centered radicals is a necessary but insufficient criterion for antimalarial activity of 1 and synthetic peroxides.

A Convenient Method for the Preparation of 4(e)-Hydroxy- and 4(e)-Methoxyadamantan-2-ones

Hydrolysis or methanolysis of 4(a)-(trifluoromethylsulfonyloxy)adamantan-2-one affords 4(e)-hydroxy- or 4(e)-methoxyaddamantan-2-one, respectively, as major product, both of which are easily separated from minor by-products.