264191-34-6

Upstream product

• 106872-64-4 1,6-bis(4-methoxycarbonylbenzylidene)hexanediamine 
• 1571-08-0 methyl 4-formylbenzoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 124-09-4 1,6-Hexanediamine 
• 264191-32-4 N,N'-bis(4-methoxycarbonylbenzyl)-1,6-hexanediamine 
• 264191-33-5 N,N'-bis(tert-butoxycarbonyl)-N,N'-bis(4-methoxycarbonylbenzyl)-1,6-hexanediamine 

Downstream Products

• 264191-35-7 N,N'-bis(tert-butoxycarbonyl)-N,N'-bis(4-chloromethylbenzyl)-1,6-hexanediamine 
• 264191-36-8 N,N'-bis(tert-butoxycarbonyl)-N,N'-bis(4-azidomethylbenzyl)-1,6-hexanediamine 
• 264191-37-9 N,N'-bis(4-azidomethylbenzyl)-1,6-hexanediamine 

Relevant academic research and scientific papers

Efficient synthesis of a hetero[4]rotaxane by a threading-stoppering- followed-by-clipping approach

A "threading-stoppering-followed-by-clipping" approach was used for the synthesis of a hetero[4]rotaxane, in which one cucurbit[6]uril (CB[6]) and two hetero crown ether macrocycles are threaded onto one dumbbell-shaped molecule. The process involves three steps: (1) threading of a CB[6] macrocycle onto a thread containing two dialkylammonium sites to form a CB[6]-based pseudo[2]rotaxane; (2) stoppering of the as-formed pseudo[2]rotaxane by imine condensation reaction followed by reduction/protonation to afford a CB[6]-based [2]rotaxane with two new dialkylammonium sites; and (3) selective clipping of two hetero crown ether macrocycles onto the newly-formed ammonium sites and subsequent reduction of the imine bonds in each crown ether to afford the final hetero[4]rotaxane in good yield. The whole process was followed by NMR spectroscopy and the structure of the hetero[4]rotaxane was confirmed by NMR spectroscopy, elemental analysis and mass spectrometry. The Royal Society of Chemistry 2010.

Synthesis of [ n ]rotaxanes by template-directed clipping: The role of the dialkylammonium recognition sites

Linear and rectangular [n]rotaxanes were synthesized by template-directed clipping of heterocrown ether components onto the dumbbell-shaped molecules containing different dialkylammonium recognition sites. The effect of the structure of the dialkylammoniu

Dual-mode "co-conformational" switching in catenanes incorporating bipyridinium and dialkylammonium recognition sites

Three [2]catenanes and three [3]catenanes incorporating one or two π-electron-rich macrocyclic polyethers and one π-electron-deficient polycationic cyclophane have been synthesized in yields ranging from 4 to 38%. The π-electron-rich macrocyclic component

Molecular Shuttles by the Protecting Group Approach

Two new [2]rotaxane-based molecular shuttles, in which a mechanically bound dibenzo[24]crown-8 (DB24C8) macroring shunts back and forth between two dialkylammonium recognition sites situated on a chemical dumbbell, have been constructed by a novel synthetic strategy that relies upon the use of the tert-butoxycarbonyl (Boc) protecting group. During the syntheses of both molecular shuttles, this protecting group masks a dialkylammonium recognition center which is liberated only after the [2]rotaxane constitution is established. In both cases, the molecular shuttles' other dialkylammonium center is essential for the rotaxane-forming reactions and it ensures that DB24C8 is interpenetrated by threadlike precursors, as a result of noncovalent bonding interactions, to produce [2]pseudorotaxanes which are stoppered subsequently through 1,3-dipolar cycloadditions between azides and bulky acetylenedicarboxylates. The new molecular shuttles have been examined by means of dynamic 1H NMR spectroscopy, which reveals that the movements of the DB24C8 macroring are very highly dependent both on solvent properties and on the nature of the spacer unit linking the two dialkylammonium centers. Thus, DB24C8 shunts facilely between the dialkylammonium centers when the shuttles are dissolved in solvents that readily donate their nonbonding electrons into noncovalent bonds, e.g., DMF, and when spacer units that do not offer much steric resistance to shuttling, e.g., hexamethylene, are used. On the other hand, shuttling is difficult in solvents that are less inclined to donate their electrons into noncovalent bonds, e.g., (CDCl2)2, and when relatively bulky benzenoid spacer units, e.g., p-xylylene, link the two dialkylammonium centers. It has been proposed that the DB24C8 might act as a "ferry" which carries a proton between dialkylammonium and dialkylamine moieties in a singly protonated [2]rotaxane by means of ion-dipole interactions.