476169-18-3Relevant academic research and scientific papers
Three different types of chirality-driven crystallization within the series of uniformly substituted phenyl glycerol ethers
Bredikhin, Alexander A.,Bredikhina, Zemfira A.,Novikova, Victorina G.,Pashagin, Alexander V.,Zakharychev, Dmitry V.,Gubaidullin, Aidar T.
, p. 1092 - 1103 (2015/02/05)
Seven chiral arylglycerol ethers 2-R-C6H4-O-CH2CH(OH)CH2OH (R 5 H, Me, Et, Allyl, n-Pr, i-Pr, tert-Bu) were synthesized in racemic and scalemic form. The IR spectra, melting points, and enthalpies of fusion for racemic and scalemic samples of every species were measured, the entropies of enantiomers mixing in the liquid state and Gibbs free energies of a racemic compound formation were derived and binary phase diagrams were reconstructed for the whole family. Solid racemic compounds stabilities were ranked for the four substances. Spontaneous resolution was established for the registered chiral drug mephenesin and its ethyl analogue. Metastable anomalous conglomerate, forming crystals having three independent R and one independent S molecules in the unit cell, is formed during solution crystallization of tert-butyl derivative; metastable phase transforms slowly into traditional racemic conglomerate. Chirality 20:1092-1103, 2008.
Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers. 31P NMR analysis of the enantiomeric composition of oxiranes
Bredikhin,Strunskaya,Novikova,Azancheev,Sharafutdinova,Bredikhina
, p. 213 - 218 (2007/10/03)
The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by 31P NMR using optically active substituted 2-chloro-1,3,2- dioxaphospholanes. A synthesis of β-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously obtained (S)-3-aryloxypropane-1,2- diols was proposed.
Systematic search for conglomerates among glycerol aromatic monoethers: Guaifenesin and mephenesin are the cases
Bredikhin, Alexander A.,Bredikhina, Zemfira A.,Lazarev, Sergey N.,Savel'ev, Dmitry V.
, p. 104 - 105 (2007/10/03)
Within the family of biologically active 3-aryloxy-1,2-propanediols, three new conglomerate-forming compounds have been found and resolved into enantiomers using the entrainment procedure.
Cyclic sulfites, key intermediates in synthesis of 1-alkylamino-3-aryloxy-2-propanols from glycidol
Bredikhina,Savel'ev,Bredikhin
, p. 213 - 219 (2007/10/03)
A number of 3-aryloxypropanedioles were obtained by treating glycidol with phenols. The latter with thionyl chloride afforded 4-aryloxymethyl-1,3,2-dioxathiolane 2-oxides. These compounds were also obtained from 4-chloromethyl-1,3,2-dioxathiolane 2-oxides by substitution aryloxy group for chlorine. The cyclic sulfides synthesized are universal intermediates in the synthesis of chiral aryloxypropanolamines among which are known β-adrenoblockaders, cardiovascular drugs. From (S)-glycidol, (S)-alprenolol, (S)-propanolol, and (S)-thymolol were synthesized.
