메뉴 건너뛰기




Volumn 20, Issue 10, 2008, Pages 1092-1103

Three different types of chirality-driven crystallization within the series of uniformly substituted phenyl glycerol ethers

Author keywords

Anomalous conglomerate; Mephenesin; Preferential crystallization; Spontaneous resolution; Thermochemistry; X ray diffraction

Indexed keywords

3 (2 ALLYLPHENOXY) PROPANE 1,2 DIOL; 3 (2 ETHYLPHENOXY) PROPANE 1,2 DIOL; 3 (2 ISOPROPYLPHENOXY) PROPANE 1,2 DIOL; 3 (2 METHYLPHENOXY) PROPANE 1,2 DIOL; 3 (2 PROPYLPHENOXY) PROPANE 1,2 DIOL; 3 (2 TERT BUTYLPHENOXY) PROPANE 1,2 DIOL; 3 PHENOXYPROPANE 1,2 DIOL; GLYCEROL ETHER; MEPHENESIN; UNCLASSIFIED DRUG;

EID: 59749084388     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20648     Document Type: Article
Times cited : (31)

References (31)
  • 1
    • 0000514268 scopus 로고
    • Sur les relations qui peuvent exister entre la forme cristalline, la composition chimique et le sens de la polarisation rotatoire
    • Pasteur L. Sur les relations qui peuvent exister entre la forme cristalline, la composition chimique et le sens de la polarisation rotatoire. Ann Chim Phys 1848;24:442-460.
    • (1848) Ann Chim Phys , vol.24 , pp. 442-460
    • Pasteur, L.1
  • 2
    • 34249656306 scopus 로고    scopus 로고
    • Spontaneous resolution, whence and whither: From enantiomorphic solids to chiral liquid crystals, monolayers and macro- and supramolecular polymers and assemblies
    • Perez-Garcia L, Amabilino DB. Spontaneous resolution, whence and whither: from enantiomorphic solids to chiral liquid crystals, monolayers and macro- and supramolecular polymers and assemblies. Chem Soc Rev 2007;36:941-967.
    • (2007) Chem Soc Rev , vol.36 , pp. 941-967
    • Perez-Garcia, L.1    Amabilino, D.B.2
  • 4
    • 33846701065 scopus 로고    scopus 로고
    • Preferential crystallization
    • Coquerel G. Preferential crystallization. Top Curr Chem 2007;269:1-51.
    • (2007) Top Curr Chem. , vol.269 , pp. 1-51
    • Coquerel, G.1
  • 5
    • 0033046564 scopus 로고    scopus 로고
    • Characterization of racemic species of chiral drugs using thermal analysis, thermodynamic calculation, and structural studies
    • Li ZJ, Zell MT, Munson EJ, Grant D J W. Characterization of racemic species of chiral drugs using thermal analysis, thermodynamic calculation, and structural studies. J Pharm Sci 1999;88:337-346.
    • (1999) J Pharm Sci , vol.88 , pp. 337-346
    • Li, Z.J.1    Zell, M.T.2    Munson, E.J.3    Grant, D.J.W.4
  • 7
    • 3042724773 scopus 로고    scopus 로고
    • Symmetry breaking by spontaneous crystallization-is it the most plausible source of terrestrial handedness we have long been looking for?-A reappraisal
    • Avalos M, Babiano R Cintas P, Jimenez JL, Palacios JC. Symmetry breaking by spontaneous crystallization-is it the most plausible source of terrestrial handedness we have long been looking for?-A reappraisal. Orig Life Evol Biosphere 2004;34:391-405.
    • (2004) Orig Life Evol Biosphere , vol.34 , pp. 391-405
    • Avalos, M.1    Cintas, B.R.P.2    Jimenez, J.L.3    Palacios, J.C.4
  • 8
    • 70449345550 scopus 로고    scopus 로고
    • 14th ed. Whitehouse Station, NJ: Merck and Co
    • O'Neil MJ, editor. The Merck Index, 14th ed. Whitehouse Station, NJ: Merck and Co; 2006.
    • (2006) The Merck Index
    • O'Neil, M.J.1
  • 9
    • 84900254060 scopus 로고    scopus 로고
    • Cyclic sulfites-the key intermediates in the synthesis of 1-alkylamino-3-aryloxypropan-2-ols from glycidol
    • Bredikhina ZA Savel'ev DV, Bredikhin AA. Cyclic sulfites-the key intermediates in the synthesis of 1-alkylamino-3-aryloxypropan-2-ols from glycidol. Russ J Org Chem 2002;38:213-219.
    • (2002) Russ J Org Chem. , vol.38 , pp. 213-219
    • Bredikhina, Z.A.1    Savel'ev, D.V.2    Bredikhin, A.A.3
  • 10
    • 33845233120 scopus 로고    scopus 로고
    • Solid state properties and effective resolution procedure for guaifenesin, 3-(2-metoxyphenoxy)-1, 2-propanediol
    • Bredikhina ZA Novikova VG, Zakharychev DV, Bredikhin AA. Solid state properties and effective resolution procedure for guaifenesin, 3-(2-metoxyphenoxy)-1, 2-propanediol. Tetrahedron: Asymmetry 2006;17:3015-3020.
    • (2006) Tetrahedron: Asymmetry , vol.17 , pp. 3015-3020
    • Bredikhina, Z.A.1    Novikova, V.G.2    Zakharychev, D.V.3    Bredikhin, A.A.4
  • 11
    • 33747083824 scopus 로고    scopus 로고
    • Crystallization of chiral compounds 3. 3-Phenoxypropane-1, 2-diol and 3-(2-halophenoxy) propane-1, 2-diols
    • Zakharychev DV, Lazarev SN, Bredikhina ZA Bredikhin AA. Crystallization of chiral compounds 3. 3-Phenoxypropane-1, 2-diol and 3-(2-halophenoxy) propane-1, 2-diols. Rus Chem Bull Int Ed 2006;55:230-237.
    • (2006) Rus Chem Bull Int Ed , vol.55 , pp. 230-237
    • Zakharychev, D.V.1    Lazarev, S.N.2    Bredikhina, Z.A.3    Bredikhin, A.A.4
  • 12
    • 34548536145 scopus 로고    scopus 로고
    • Spontaneous resolution among chiral glycerol derivatives: Crystallization features of ortho-alkoxysubstituted phenyl glycerol ethers
    • Bredikhin AA, Bredikhina ZA Zakharychev DV, Konoshenko LV. Spontaneous resolution among chiral glycerol derivatives: crystallization features of ortho-alkoxysubstituted phenyl glycerol ethers. Tetrahedron: Asymmetry 2007;18:1964-1970.
    • (2007) Tetrahedron: Asymmetry , vol.18 , pp. 1964-1970
    • Bredikhin, A.A.1    Bredikhina, Z.A.2    Zakharychev, D.V.3    Konoshenko, L.V.4
  • 14
    • 0032579179 scopus 로고    scopus 로고
    • Baker's yeast mediated stereoselective biotransformation of 1-acetoxy-3-aryloxypropan-2-ones
    • Egri G, Kolbert A, Balint J, Fogassy E, Novak L, Poppe L. Baker's yeast mediated stereoselective biotransformation of 1-acetoxy-3-aryloxypropan-2-ones. Tetrahedron: Asymmetry 1998;9:271-283.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 271-283
    • Egri, G.1    Kolbert, A.2    Balint, J.3    Fogassy, E.4    Novak, L.5    Poppe, L.6
  • 15
    • 0033544768 scopus 로고    scopus 로고
    • CsF in organic synthesis. Regioselective nucleophilic reaction of phenols with oxiranes leading to enantiopure b-blockers
    • Kitaory K, Furukawa Y, Yoshimoto H, Otera J. CsF in organic synthesis. Regioselective nucleophilic reaction of phenols with oxiranes leading to enantiopure b-blockers. Tetrahedron 1999;55:14381-14390.
    • (1999) Tetrahedron , vol.55 , pp. 14381-14390
    • Kitaory, K.1    Furukawa, Y.2    Yoshimoto, H.3    Otera, J.4
  • 16
    • 0041564171 scopus 로고    scopus 로고
    • Systematic search for conglomerates among glycerol aromatic monoethers: Guaifenesin and mephenesin are the cases
    • Bredikhin AA, Bredikhina ZA Lazarev SN, Savel'ev DV. Systematic search for conglomerates among glycerol aromatic monoethers: guaifenesin and mephenesin are the cases. Mendeleev Commun 2003;13:104-105.
    • (2003) Mendeleev Commun , vol.13 , pp. 104-105
    • Bredikhin, A.A.1    Bredikhina, Z.A.2    Lazarev, S.N.3    Savel'ev, D.V.4
  • 17
    • 0028281892 scopus 로고
    • Kinetic resolution of acyclic 1, 2-diols using a sequential lipase-catalyzed transesterifications in organic solvents
    • Theil F, Weidner J, Ballschuh S, Kunath A, Schick H. Kinetic resolution of acyclic 1, 2-diols using a sequential lipase-catalyzed transesterifications in organic solvents. J Org Chem 1994;59:388-393.
    • (1994) J Org Chem. , vol.59 , pp. 388-393
    • Theil, F.1    Weidner, J.2    Ballschuh, S.3    Kunath, A.4    Schick, H.5
  • 18
    • 33747044585 scopus 로고
    • Physiologically active substituted a-glyceryl phenyl ethers
    • Lambooy JP. Physiologically active substituted a-glyceryl phenyl ethers. J Am Chem Soc 1951;73:349-350.
    • (1951) J Am Chem Soc , vol.73 , pp. 349-350
    • Lambooy, J.P.1
  • 19
    • 0000132279 scopus 로고
    • Muscle-relaxing compounds similar to 3-(o-toloxy)-1, 2-propanediol. I. Aromatic ethers of polyhydroxy alcohols and related compounds
    • Yale HL, Pribyl EJ, Braker W, Bergeim FH, Lott WA Muscle-relaxing compounds similar to 3-(o-toloxy)-1, 2-propanediol. I. Aromatic ethers of polyhydroxy alcohols and related compounds. J Am Chem Soc 1950;72:3710-3716.
    • (1950) J Am Chem Soc , vol.72 , pp. 3710-3716
    • Yale, H.L.1    Pribyl, E.J.2    Braker, W.3    Bergeim, F.H.4    Lott, W.A.5
  • 20
    • 0016335355 scopus 로고
    • Anxiolytic activity derived from a myorelaxant structure. Tert-Butylphenol derivatives
    • Auzou G, Rips R Derappe C, Peyroux J. Anxiolytic activity derived from a myorelaxant structure. tert-Butylphenol derivatives. Eur J Med Chem Chim Ther 1974;9:548-554.
    • (1974) Eur J Med Chem Chim Ther , vol.9 , pp. 548-554
    • Auzou, G.1    Rips, R.2    Derappe, C.3    Peyroux, J.4
  • 23
    • 0141452964 scopus 로고    scopus 로고
    • WinGX 1.64.05. An integrated system of Windows programs for the solution, refinement and analysis of single crystal X-ray diffraction data
    • Farrugia LJ. WinGX 1.64.05. An integrated system of Windows programs for the solution, refinement and analysis of single crystal X-ray diffraction data. J Appl Crystalogr 1999;32:837-838.
    • (1999) J Appl Crystalogr , vol.32 , pp. 837-838
    • Farrugia, L.J.1
  • 24
    • 0001792356 scopus 로고    scopus 로고
    • Single-crystal structure validation with the program PLA-TON
    • Spek AL. Single-crystal structure validation with the program PLA-TON. J Appl Cryst 2003;36:7-13.
    • (2003) J Appl Cryst , vol.36 , pp. 7-13
    • Spek, A.L.1
  • 25
    • 84944438568 scopus 로고
    • On enantiomorph polarity estimation
    • Flack HD. On enantiomorph polarity estimation. Acta Crystallogr Sect A 1983;39:876-881.
    • (1983) Acta Crystallogr Sect A , vol.39 , pp. 876-881
    • Flack, H.D.1
  • 26
    • 0034474897 scopus 로고    scopus 로고
    • Reporting end evaluating absolute structure and absolute configuration determination
    • Flack HD, Bernardinelli G. Reporting end evaluating absolute structure and absolute configuration determination. J Appl Crystallogr 2000;33:1143-1148.
    • (2000) J Appl Crystallogr , vol.33 , pp. 1143-1148
    • Flack, H.D.1    Bernardinelli, G.2
  • 27
    • 0004860970 scopus 로고
    • Séparation des tartrates gauches et des tartrates droits à l'aide des solutions sursaturées
    • Gernez. Séparation des tartrates gauches et des tartrates droits à l'aide des solutions sursaturées. Compt Rend 1866;63:843.
    • (1866) Compt Rend , vol.63 , pp. 843
    • Gernez1
  • 28
    • 84864240516 scopus 로고
    • Verfahren zur Scheidung rechtsdrehend- und linksdrehendweinsaurer Salze
    • Gernez. Verfahren zur Scheidung rechtsdrehend- und linksdrehendweinsaurer Salze. Ann Chem Pharm 1867;143:376.
    • (1867) Ann Chem Pharm , vol.143 , pp. 376
    • Gernez1
  • 29
    • 0842348999 scopus 로고    scopus 로고
    • A Priori assessment of the maximum possible entrainment effect attainable during preferential crystallization. The case of the simultaneous resolution of (±)-ephedrine and (±)-mandelic acid
    • Dufour F, Perez G, Coquerel G. A Priori assessment of the maximum possible entrainment effect attainable during preferential crystallization. The case of the simultaneous resolution of (±)-ephedrine and (±)-mandelic acid. Bull Chem Soc Jpn 2004;77:79-86.
    • (2004) Bull Chem Soc Jpn , vol.77 , pp. 79-86
    • Dufour, F.1    Perez, G.2    Coquerel, G.3
  • 30
    • 0033638591 scopus 로고    scopus 로고
    • Review on the heterogeneous equilibria between condensed phases in binary systems of enantiomers
    • Coquerel G. Review on the heterogeneous equilibria between condensed phases in binary systems of enantiomers. Enantiomer 2000;3:481-498.
    • (2000) Enantiomer , vol.3 , pp. 481-498
    • Coquerel, G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.