새로운 비스-크라운 에테르류의 합성 (제 1 보) : 실옥산 사슬에 연결된 크라운 에테르

Syntheses of Novel Bis-Crown Ethers(Ⅰ) : Crown Ethers with Siloxane Moiety

  • 장승현 (대구대학교 자연과학대학 화학과) ;
  • 김재용 (대구대학교 자연과학대학 화학과)
  • 발행 : 19940500

초록

실옥산 사슬과 크라운 에테르가 연결된 유연성이 큰 2가지 새로운 비스-크라운 에테르를 합성하였다. 1,3-Bis(trimethylsiloxy)-1,3-dimethyl-1,3-dipentaoxacyclohexadecamethyl disiloxane(1)는 백금촉매 존재하에서 3-methylene-16-crown-5 (8)과 1,3-bis(trimethylsiloxy)-1,3-dimethyl disiloxane (10)의 반응에 의해 합성하였다. 1,1,3,3,5,5-Hexamethyl-1,5-dipentaoxacyclohexadecamethyl trisiloxane (2)은 백금촉매 존재하에서 crown ether (8)과 1,1,3,3,5,5-hexamethyl trisiloxane (11)의 반응에 의해 합성하였다. 3-Methylene-13-crown-4 (7), 3-methylene-16-crown-5 (8), 및 3-methylene-19-crown-6 (9)은 NaH 존재하에서 triethylene glycol (3), tetraethylene glycol (4), 및 pentaethylene glycol (5)을 각각 3-chloro-2-chloro-methyl-1-propene (6)와 반응시켜서 합성하였다.

New bis-crown ethers containing siloxane chain were synthesized. 1,3-Bis(trimethylsiloxy)-1,3-dimethyl-1,3-dipentaoxacyclohexadecamethyl disiloxane (1) was synthesized by reaction of 3-methylene-16-crown-5 (8) with 1,3-bis(trimethylsiloxy)-1,3-dimethyl disiloxane (10) in the presence of Pt catalyst. 1,1,3,3,5,5-Hexamethyl-1,5-dipentaoxacyclohexadecamethyl trisiloxane (2) was synthesized by the reaction of crown ether (8) with 1,1,3,3,5,5-hexamethyl trisiloxane (11) in the presence of Pt catalyst. 3-Methylene-13-crown-4 (7), 3-methylene-16-crown-5 (8), and 3-methylene-19-crown-6 (9) were synthesized by the reaction of triethylene glycol (3), tetraethylene glycol (4), and pentaethylene glycol (5) respectively with 3-chloro-2-chloro-methyl-1-propene (6) in the presence of NaH.

키워드

참고문헌

  1. J. Am. Chem. Soc v.89 Perdersen, C. J.
  2. Tetrahedron Lett. v.23 Minami, T.;Shinkai, S.;Manabe, O.
  3. J. Am. Chem. Soc. v.102 Lamb, J. D.;Izatt, R. M.;Swain, C. S.;Bradshaw, J. S.;Christensene, J. J.
  4. Science v.257 O'Neil, M. P.;Niemczyk, M. P.;Svec, W. A.;Gosztola, D.;Gaines III, G. L.;Wasielewski, M. R.
  5. J. Org. Chem. v.55 Bradshaw, J. S.;Huszthy, P.;McDaniel, C. W.;Zhu, C. Y.;Dalley, N. K.;Izatt, R. M.
  6. Anal. Chem. v.62 Payne, K. M.;Tarbet, B. J.;Bradshaw, J. S.;Markides, K. E.;Lee, M. L.
  7. J. Am. Chem. Soc. v.93 Frensdroff, H. K.
  8. J. Kor. Chem. Soc. v.33 Chang, S. H.;Yoon, M. H.;Kim, C. S.;Chung, K. B.;Shim, J. H.
  9. J. Kor. Chem. Soc. v.32 Chang, S. H.;Chung, K. B.;Sung, Y. K.;Kim, T. K.;Shim, J. H.
  10. Absts, 9th International Conference on Organic Synthesis Chang, S. H.;Kim, D. J.
  11. J. Kor, Chem. Soc. v.38 Chang, S. H.;Kim, D. J.;Kim, J. Y.;Lee, K. D.
  12. Tetrahedron Lett. v.34 Dietrich, B.;Lehn, J. M.;Sauvage, J. P.
  13. J. Am. Chem. Soc. v.103 Shinkai, S.;Nakaji, T.;Ogawa, T.;Shigematsu, K.;Manabe, O.
  14. J. Chem. Soc. Chem. Commun. Kimura, E.;Fujioka, H.;Kodama, M.
  15. Tetrahedron Lett. Tomoi, M.;Abe, O.;Ikeda, M.;Kihara, K.;Kakiuchi, H.
  16. Tetrahedron Lett. Reinhoudt, D. N.;Jong, de F.;Tomassen, H. P.
  17. Macrocyclic Chemistry;Aspects of Organic and Inorganic Supramolecular Chemistry Dietrich, B.;Viout, P.;Lehn, J. M.
  18. Pure and Appl. Chem. v.61 Bradshaw, J. S.;Krakowiak, K. E.;Tarbet, B. J.;Bruening, R. L.;Briernat, J. F.;Bochenska, M.;Izatt, R. M.;Christensen, J. J.
  19. Tetrahedron v.29 Dietrich, B.;Lehn, J. M.;Sauvage, J. P.;Blanzat, J.
  20. J. Inclus. Phenom. v.6 Lehn, J. M.
  21. J. Chem. Soc. Chem. Commun. Lehn, J. M.;Malthete, J.;Levelut, A. M.
  22. J. Org. Chem. v.43 Cram, D. J.;Helgeson, R. C.;Koga, K.;Kyba, E. P.;Madan, K.;Sousa, L. R.;Siegel, M. G.;Moreau, P.;Gokel, G. W.;Timko, J. M.;Sogah, G. Dotsevi Y.
  23. J. Am. Chem. Soc. v.107 Cram, D. J.;Kaneda, T.;Helgeson, R. C.;Brown, S. B.;Knobler, C. B.;Maverick, E.;Trueblood, K. N.
  24. J. Chem. Soc. Chem. Commun. Kubo, Y.;Hamaguchi, S. I.;Niimi, A.;Yoshida, K.;Tokita, S.
  25. J. Chem. Soc., Chem. Commun. Beer, P. D.