The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom.Quality Control of Dimethoxydiphenylmethane
Banerjee, Ashutosh;Schepmann, Dirk;Koehler, Jens;Wuerthwein, Ernst-Ulrich;Wuensch, Bernhard published 《Synthesis and SAR studies of chiral non-racemic dexoxadrol analogues as uncompetitive NMDA receptor antagonists》. The research results were published in《Bioorganic & Medicinal Chemistry》 in 2010.Quality Control of Dimethoxydiphenylmethane The article conveys some information:
A series of chiral non-racemic dexoxadrol analogs with various substituents in position 4 of the piperidine ring was synthesized and pharmacol. evaluated. Only the enantiomers having (S)-configuration at the 2-position of the piperidine ring and 4-position of the dioxolane ring were considered. Key steps in the synthesis were an imino-Diels-Alder reaction of enantiomerically pure imine (S)-13, which had been obtained from D-mannitol, with Danishefsky’s Diene 14 and the replacement of the p-methoxybenzyl protective group with a Cbz-group. It was shown that (S,S)-configuration of the ring junction (position 2 of the piperidine ring and position 4 of the dioxolane ring) and axial orientation of the C-4-substituent ((4S)-configuration) are crucial for high NMDA receptor affinity. 2-(2,2-Diphenyl-1,3-dioxolan-4-yl)piperidines with a hydroxy moiety ((S,S,S)-5 (I), Ki = 28 nM), a fluorine atom ((S,S,S)-6 (II), WMS-2539, Ki = 7 nM) and two fluorine atoms ((S,S)-7 (III), Ki = 48 nM) in position 4 represent the most potent NMDA antagonists with high selectivity against σ1 and σ2 receptors and the polyamine binding site of the NMDA receptor. The NMDA receptor affinities of the new ligands were correlated with their electrostatic potentials, calculated gas phase proton affinities (neg. enthalpies of deprotonation) and dipole moments. According to these calculations decreasing proton affinity and increasing dipole moment are correlated with decreasing NMDA receptor affinity. The experimental procedure involved many compounds, such as Dimethoxydiphenylmethane (cas: 2235-01-0) .
The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom.Quality Control of Dimethoxydiphenylmethane
Reference:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem