70546-85-9

Upstream product

• 4801-58-5 N-hydroxypiperidine 
• 100-42-5 styrene 
• 34418-91-2 2,3,4,5-tetrahydropyridine N-oxide 

Downstream Products

• 127983-45-3 6-(2'-hydroxy-2'-phenylethyl)-2,3,4,5-tetrahydropyridine 
• 128001-85-4 (S)-1-Phenyl-2-((2S,3aR,7R)-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-7-yl)-ethanol 
• 105147-78-2 2-(1-Oxy-2,3,4,5-tetrahydro-pyridin-2-yl)-1-phenyl-ethanol 
• 105147-78-2 (S)-2-((R)-1-Oxy-2,3,4,5-tetrahydro-pyridin-2-yl)-1-phenyl-ethanol 
• 495-47-6 2-(2'-hydroxy-2'-phenylethyl)piperidine 
• 70546-72-4 (2S,3aR)-8-Methyl-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; iodide 
• 70561-78-3 (2R,3aS,8S)-8-Methyl-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; iodide 
• 497-88-1 sedamine 
• 70546-72-4 (2R,3aR)-8-Methyl-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; iodide 
• 105147-79-3 (2R,3aS,7S)-8-Benzyl-7-(2-hydroxy-2-phenyl-ethyl)-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; bromide 
• 105147-81-7 (2S,6S)-1-Benzyl-2,6-diphenethyl-piperidine 
• 131697-74-0 (2S,3aR)-8-Benzyl-3a-methyl-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; bromide 
• 127983-46-4 cis-6-methyl-8-phenyl-9-oxa-1-azabicyclo<4.3.0>nonane 
• 142749-20-0 (R)-2-((S)-2-Hydroxy-2-phenyl-ethyl)-piperidin-1-ol 

Relevant academic research and scientific papers

Nitrone Cycloadditions: Synthesis of (+/-)-Andrachamine

The usefulness of the cycloaddition of alkenes to 2-alkyl-2,3,4,5-tetrahydropyridine oxides for the preparation of trans-2,6-dialkylpiperidines is confirmed by a stereoselective synthesis of (+/-)-andrachamine.Peroxy acid oxidation of 9-oxa-1-azabicyclononanes does not lead regioselectively to the corresponding 2-alkyl-2,3,4,5-tetrahydropyridine oxide, as had previously been claimed.

REACTIVITY, REGIOCHEMISTRY, AND STEREOCHEMISTRY OF A CYCLIC NITRONE AND ITS α-KETO DERIVATIVE IN 1,3-DIPOLAR CYCLOADDITION REACTIONS

Rate constants for the cycloadditions of 3,4,5,6-tetrahydropyridine 1-oxide (1), and 3-oxo-3,4,5,6-tetrahydropyridine 1-oxide (2) to several mono- and disubstituted alkenes have been determined at 36 deg C by 1H NMR Spectroscopy.Small solvent effect on the rate constant indicate the concerted nature of the reaction.It is found that nitrone 2 reacts slower than 1 because of the presence of bond opposition strain in the transition state for the former nitrone.Addition rates are influenced by the dipole moments of the nitrones.Reactivity of these addition reactions usually follows the prediction of frontier orbital approximation.Both the nitrones exhibit very similar regiochemical and stereochemical properties.Significant secondary orbital interaction is observed with several electron deficient alkenes.However, maleic anhydride is found to undergo addition predominantly via exo mode of attack.

THE CYCLOADDITION REACTION BETWEEN STYRENE AND 2,3,4,5-TETRAHYDROPYRIDINE 1-OXIDE

The cycloaddition of styrene to 2,3,4,5-tetrahydropyridine 1-oxide leads, with a high yield, to a 97:3 mixture of the diastereoisomeric isoxazolidines 3c and 4c respectively.

THE α,α'-DIALKYLATION OF CYCLIC AMINES. THE SYNTHESIS OF SOLENOPSIS ANT VENOMS.

A trans-α,α'-dialkylation of cyclic amines has been investigated through the use of nitrone methodology.This procedure has been utilized in the synthesis of Solenopsis ant venoms.