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Volumn 9, Issue 5, 2007, Pages 915-918

Calixcyclitols: A new class of polar hybrid hosts obtained by oxygenation of calixarene phenol rings

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EID: 33947106041     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0701161     Document Type: Article
Times cited : (20)

References (52)
  • 1
    • 33748539998 scopus 로고
    • For general reviews on calixarenes, see: a
    • For general reviews on calixarenes, see: (a) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
    • (1995) Angew. Chem., Int. Ed. Engl , vol.34 , pp. 713
    • Böhmer, V.1
  • 3
    • 0004268367 scopus 로고    scopus 로고
    • Royal Society of Chemistry: Cambridge
    • (c) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998.
    • (1998) Calixarenes Revisited
    • Gutsche, C.D.1
  • 4
    • 0004287470 scopus 로고    scopus 로고
    • Asfari, Z, Böhmer, V, Harrowfield, J, Vicens J, Eds, Kluwer: Dordrecht
    • (d) Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens J., Eds.; Kluwer: Dordrecht, 2001.
    • (2001) Calixarenes 2001
  • 5
    • 0007154316 scopus 로고    scopus 로고
    • Asfari, Z, Böhmer, V, Harrowfield, J, Vicens, J, Eds, Kluwer: Dordrecht, Chapter 25, pp
    • (a) Arduini, A.; Pochini, A.; Secchi, A.; Ugozzoli, F. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer: Dordrecht, 2001; Chapter 25, pp 457-475.
    • (2001) Calixarenes 2001 , pp. 457-475
    • Arduini, A.1    Pochini, A.2    Secchi, A.3    Ugozzoli, F.4
  • 8
    • 0008795323 scopus 로고    scopus 로고
    • Asfari, Z, Böhmer, V, Harrowfield, J, Vicens, J, Eds, Kluwer Academic Publishers: Dordrecht, Chapter 15, pp
    • (a) Rudkevich, D. M. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; Chapter 15, pp 155-180.
    • (2001) Calixarenes 2001 , pp. 155-180
    • Rudkevich, D.M.1
  • 18
    • 2242456206 scopus 로고    scopus 로고
    • Asfari, Z, Böhmer, V, Harrowfield, J, Vicens J, Eds, Kluwer: Dordrecht, Chapter 13, pp
    • (d) Vysotsky, M.; Saadioui, M.; Böhmer, V. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens J., Eds.; Kluwer: Dordrecht, 2001; Chapter 13, pp 250-265.
    • (2001) Calixarenes 2001 , pp. 250-265
    • Vysotsky, M.1    Saadioui, M.2    Böhmer, V.3
  • 22
    • 0003110217 scopus 로고    scopus 로고
    • For a review on the oxidation and reduction of calixarene aromatic rings, see: a, Asfari, Z, Böhmer, V, Harrowrïeld, J, Vicens J, Eds, Kluwer: Dordrecht, Chapter 14, pp
    • For a review on the oxidation and reduction of calixarene aromatic rings, see: (a) Biali, S. E. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowrïeld, J., Vicens J., Eds.; Kluwer: Dordrecht, 2001; Chapter 14, pp 266-279.
    • (2001) Calixarenes 2001 , pp. 266-279
    • Biali, S.E.1
  • 28
    • 0032545006 scopus 로고    scopus 로고
    • For examples of calixcyclohexanol derivatives, see ref 7a and: (a) Columbus, I, Haj-Zaroubi, M, Biali, S. E. J. Am. Chem. Soc. 1998, 120, 11806 and references therein
    • For examples of calixcyclohexanol derivatives, see ref 7a and: (a) Columbus, I.; Haj-Zaroubi, M.; Biali, S. E. J. Am. Chem. Soc. 1998, 120, 11806 and references therein.
  • 31
    • 33947118480 scopus 로고    scopus 로고
    • Polar, nonionic, calixarene derivatives have also been obtained by appending hydrophilic groups: (a) Grote Gansey, M. H. B.; Steemers, F. J.; Verboom, W.; Reinhoudt, D. N. Synthesis 1997, 643.
    • Polar, nonionic, calixarene derivatives have also been obtained by appending hydrophilic groups: (a) Grote Gansey, M. H. B.; Steemers, F. J.; Verboom, W.; Reinhoudt, D. N. Synthesis 1997, 643.
  • 37
    • 33947190288 scopus 로고    scopus 로고
    • See the Supporting Information for additional details
    • See the Supporting Information for additional details.
  • 38
    • 33947125846 scopus 로고    scopus 로고
    • The X-ray analysis supports the gross structure, although the R factor was 13%.
    • The X-ray analysis supports the gross structure, although the R factor was 13%.
  • 39
    • 33947102906 scopus 로고    scopus 로고
    • This unexpected reaction outcome is likely the result of an initial epoxy interchange to give II (Payne's rearrangement: Payne, G. B. J. Org. Chem. 1962, 27, 3819, which is possible because of the trans disposition of the epoxy and secondary hydroxyl groups, Chemical Equation Presented) Reductive opening of the new epoxy group by SN2 attack of the hydride ion would then give III, in which an intramolecular S N2 attack of the alkoxide group to the second epoxide would give rise to the oxetane ring in IV
    • N2 attack of the alkoxide group to the second epoxide would give rise to the oxetane ring in IV.
  • 40
    • 38849162458 scopus 로고    scopus 로고
    • In fact, cyclitols are cycloalkanes containing one hydroxyl group on each of three or more ring atoms Angyal, S. J, Andersen, C, Cahn, R. S, Dowson, R. M. C, Hoffmann-Ostenhof, O, Klyne, W, Posternack, T. Pure Appl. Chem. 1974, 37, 283
    • In fact, cyclitols are cycloalkanes containing one hydroxyl group on each of three or more ring atoms (Angyal, S. J.; Andersen, C.; Cahn, R. S.; Dowson, R. M. C.; Hoffmann-Ostenhof, O.; Klyne, W.; Posternack, T. Pure Appl. Chem. 1974, 37, 283).
  • 46
    • 33947117722 scopus 로고    scopus 로고
    • Analogous oxygenation of 6 with t-BuOK in dry DMF for 17 h, at 80°C, followed by treatment with t-BuOOH/t-BuOK, resulted in the formation of 7 in 17% yield.
    • Analogous oxygenation of 6 with t-BuOK in dry DMF for 17 h, at 80°C, followed by treatment with t-BuOOH/t-BuOK, resulted in the formation of 7 in 17% yield.
  • 47
    • 33947132471 scopus 로고    scopus 로고
    • In accordance with a previously used notation,10 we indicate with X (or N) the ring bearing exo-epoxides or endo-epoxides
    • 10 we indicate with X (or N) the ring bearing exo-epoxides (or endo-epoxides).
  • 48
    • 33947097735 scopus 로고    scopus 로고
    • MacroModel, version 9.0; Schrödinger, LLC: New York, 2005
    • MacroModel, version 9.0; Schrödinger, LLC: New York, 2005.
  • 49
    • 33947107294 scopus 로고    scopus 로고
    • In accordance with this high difference of energy, only signals related to cone conformer 9 are present in its 1H NMR spectrum. Dynamic NMR studies (400 MHz) showed that calixcyclitol 9 is fixed in this cone conformation at room temperature and indicated a coalescence of both the ArCH2 signals at temperatures higher than 393 K in TCDE. Therefore, an energy barrier higher than 17.2 kcal/mol can be estimated for its conformational inversion. Similar higher-energy barriers for the through-the-annulus rotation of cyclohexanol rings with respect to phenol rings were previously evidenced by Biali for calixcyclohexanol derivatives. 8a,b
    • 8a,b


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.