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Volumn 65, Issue 1, 2009, Pages 137-155

O-alkyl resorcarenes: Where are we now?

Author keywords

Calixarenes, O alkyl resorcarenes; Resorcarenes; Resorcinarenes

Indexed keywords


EID: 76349102117     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-009-9623-9     Document Type: Review
Times cited : (17)

References (72)
  • 4
    • 0032512027 scopus 로고    scopus 로고
    • The synthesis of octamethoxyresorc[4]arenes catalysed by Lewis acids
    • Iwanek, W.: The synthesis of octamethoxyresorc[4]arenes catalysed by Lewis acids. Tetrahedron 54, 14089-14094 (1998).
    • (1998) Tetrahedron , vol.54 , pp. 14089-14094
    • Iwanek, W.1
  • 5
    • 0033001697 scopus 로고    scopus 로고
    • Lewis acid-induced synthesis of octamethoxyresorcarenes
    • Iwanek, W., Syzdół, B.: Lewis acid-induced synthesis of octamethoxyresorcarenes. Synth. Commun. 29, 1209-1216 (1999).
    • (1999) Synth. Commun. , vol.29 , pp. 1209-1216
    • Iwanek, W.1    Syzdół, B.2
  • 6
    • 76349115958 scopus 로고
    • First one-step synthesis of octaethyl 1, 8, 15, 22-tetra-p-tolylphenyl[1. 4]metacyclophan-3, 5, 10, 12, 17, 19, 24, 26-octayloxyoctaacetate
    • Pieroni, O. I., Gonzales Sierra, M., Cabaleiro, M. C.: First one-step synthesis of octaethyl 1, 8, 15, 22-tetra-p-tolylphenyl[1. 4]metacyclophan-3, 5, 10, 12, 17, 19, 24, 26-octayloxyoctaacetate. J. Chem. Res. 2773-2782 (1994).
    • (1994) J. Chem. Res. , pp. 2773-2782
    • Pieroni, O.I.1    Gonzales Sierra, M.2    Cabaleiro, M.C.3
  • 7
    • 0032914960 scopus 로고    scopus 로고
    • A one-step synthesis of O-functionalized resorcinarene under heterogeneous catalysis conditions
    • Vuano, B., Pieroni, O. I.: A one-step synthesis of O-functionalized resorcinarene under heterogeneous catalysis conditions. Synthesis 72-73 (1999).
    • (1999) Synthesis , pp. 72-73
    • Vuano, B.1    Pieroni, O.I.2
  • 8
    • 0034641321 scopus 로고    scopus 로고
    • Structural elucidation of two [1.4]metacyclophanes isomers by 2D NMR analysis
    • Vuano, B. M., Pieroni, O. I.: Structural elucidation of two [1. 4]metacyclophanes isomers by 2D NMR analysis. J. Mol. Struct. 525, 63-69 (2000).
    • (2000) J. Mol. Struct. , vol.525 , pp. 63-69
    • Vuano, B.M.1    Pieroni, O.I.2
  • 9
    • 0036936498 scopus 로고    scopus 로고
    • Synthesis of a novel class of carbohydrate-containing calix[4]resorcinarene adopting an asymmetrical diamond structure
    • Sakhaii, P., Verdier, L., Ikegami, T., Griesinger, C.: Synthesis of a novel class of carbohydrate-containing calix[4]resorcinarene adopting an asymmetrical diamond structure. Helv. Chim. Acta 85, 3895-3908 (2002).
    • (2002) Helv. Chim. Acta , vol.85 , pp. 3895-3908
    • Sakhaii, P.1    Verdier, L.2    Ikegami, T.3    Griesinger, C.4
  • 10
    • 0041475404 scopus 로고
    • Mechanisms of macrocycle genesis. The condensation of resorcinol with aldehydes
    • Weinelt, F., Schneider, H.-J.: Mechanisms of macrocycle genesis. The condensation of resorcinol with aldehydes. J. Org. Chem. 56, 5527-5535 (1991).
    • (1991) J. Org. Chem. , vol.56 , pp. 5527-5535
    • Weinelt, F.1    Schneider, H.-J.2
  • 13
    • 44949111257 scopus 로고    scopus 로고
    • Selective formation of the rctt chair stereoisomers of octa-O-alkyl resorcin[4]arenes using Brønsted acid catalysis
    • Moore, D., Watson, G. W., Gunnlaugsson, T., Matthews, S. E.: Selective formation of the rctt chair stereoisomers of octa-O-alkyl resorcin[4]arenes using Brønsted acid catalysis. New J. Chem. 32, 994-1002 (2008).
    • (2008) New J. Chem. , vol.32 , pp. 994-1002
    • Moore, D.1    Watson, G.W.2    Gunnlaugsson, T.3    Matthews, S.E.4
  • 14
    • 4143061575 scopus 로고    scopus 로고
    • The interaction of octamethoxyresorcinarene with halogenoacetic acids
    • Urbaniak, M., Iwanek, W.: The interaction of octamethoxyresorcinarene with halogenoacetic acids. Tetrahedron 60, 8265-8273 (2004).
    • (2004) Tetrahedron , vol.60 , pp. 8265-8273
    • Urbaniak, M.1    Iwanek, W.2
  • 23
    • 0010359049 scopus 로고
    • Synthesis of C-alkyl calix[4]arenes. 3. Acid-catalyzed rearrangement of 2, 6-dimethoxycinnamate prior to tetramerization to calix[4]arenes
    • Botta, B., Delle Monache, G., De Rosa, M. C., Carbonetti, A., Gács-Baitz, E., Botta, M., Corelli, F., Misiti, D.: Synthesis of C-alkyl calix[4]arenes. 3. Acid-catalyzed rearrangement of 2, 6-dimethoxycinnamate prior to tetramerization to calix[4]arenes. J. Org. Chem. 60, 3657-3662 (1995).
    • (1995) J. Org. Chem. , vol.60 , pp. 3657-3662
    • Botta, B.1    Delle Monache, G.2    de Rosa, M.C.3    Carbonetti, A.4    Gács-Baitz, E.5    Botta, M.6    Corelli, F.7    Misiti, D.8
  • 24
    • 0001863752 scopus 로고
    • Conformational properties of octahydroxy[1. 4]metacyclophanes with unsubstituted methylene bridges
    • Konishi, H., Morikawa, O.: Conformational properties of octahydroxy[1. 4]metacyclophanes with unsubstituted methylene bridges. J. Chem. Soc. Chem. Commun. 34-35 (1993).
    • (1993) J. Chem. Soc. Chem. Commun. , pp. 34-35
    • Konishi, H.1    Morikawa, O.2
  • 25
    • 0012718326 scopus 로고
    • Calix[6]resorcinarenes: The first examples of [16]metacyclophanes derived from resorcinols
    • Konishi, H., Ohata, K., Morikawa, O., Kobayashi, K.: Calix[6]resorcinarenes: the first examples of [16]metacyclophanes derived from resorcinols. J. Chem. Soc. Chem. Commun. 309-310 (1995).
    • (1995) J. Chem. Soc. Chem. Commun. , pp. 309-310
    • Konishi, H.1    Ohata, K.2    Morikawa, O.3    Kobayashi, K.4
  • 26
    • 0030574009 scopus 로고    scopus 로고
    • The acid-catalyzed condensation of 2-propylresorcinol with formaldehyde diethyl acetal. The formation and isomerisation of calix[4]resorcinarene, calix[5]resorcinarene and calix[6]resorcinarene
    • Konishi, H., Nakamura, T., Ohata, K., Kobayashi, K., Morikawa, O.: The acid-catalyzed condensation of 2-propylresorcinol with formaldehyde diethyl acetal. The formation and isomerisation of calix[4]resorcinarene, calix[5]resorcinarene and calix[6]resorcinarene. Tetrahedron Lett. 37, 7383-7386 (1996).
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7383-7386
    • Konishi, H.1    Nakamura, T.2    Ohata, K.3    Kobayashi, K.4    Morikawa, O.5
  • 27
    • 85064749848 scopus 로고
    • Base-catalyzed synthesis of a calix[4]resorcinarene: Cyclocondensation of 2-butyrylresorcinol with formaldehyde
    • Konishi, H., Iwasaki, Y.: Base-catalyzed synthesis of a calix[4]resorcinarene: cyclocondensation of 2-butyrylresorcinol with formaldehyde. Synlett 612 (1995).
    • (1995) Synlett , pp. 612
    • Konishi, H.1    Iwasaki, Y.2
  • 28
    • 27644500013 scopus 로고    scopus 로고
    • Synthesis of new resorcinarenes under alkaline conditions
    • Bourgeois, J.-M., Stoeckli-Evans, H.: Synthesis of new resorcinarenes under alkaline conditions. Helv. Chim. Acta 88, 2722-2730 (2005).
    • (2005) Helv. Chim. Acta , vol.88 , pp. 2722-2730
    • Bourgeois, J.-M.1    Stoeckli-Evans, H.2
  • 29
    • 0027957925 scopus 로고
    • High yield synthesis of the parent C-unsubstituted calix[4]resorcinarene octamethyl ether
    • Falana, O. M., Al-Farhan, E., Keehn, P. M., Stevenson, R.: High yield synthesis of the parent C-unsubstituted calix[4]resorcinarene octamethyl ether. Tetrahedron Lett. 35, 65-68 (1994).
    • (1994) Tetrahedron Lett. , vol.35 , pp. 65-68
    • Falana, O.M.1    Al-Farhan, E.2    Keehn, P.M.3    Stevenson, R.4
  • 31
    • 12944268199 scopus 로고    scopus 로고
    • 3-catalyzed cyclooligomerization of 2, 4-dialkoxybenzyl alcohols. Formation of resorcin[n]arene peralkyl ethers
    • 3-catalyzed cyclooligomerization of 2, 4-dialkoxybenzyl alcohols. Formation of resorcin[n]arene peralkyl ethers. Polym. Bull. 53, 97-107 (2005).
    • (2005) Polym. Bull. , vol.53 , pp. 97-107
    • Morikawa, O.1    Ishizaka, T.2    Sakakibara, H.3    Kobayashi, K.4    Konishi, H.5
  • 33
    • 0036184105 scopus 로고    scopus 로고
    • Synthesis of C-unalkylated calix[4]resorcinarene from 1, 3-dimethoxybenzene-formaldehyde condensation
    • Li, D., Kusunoki, T., Yamagishi, T.-A., Nakamoto, Y.: Synthesis of C-unalkylated calix[4]resorcinarene from 1, 3-dimethoxybenzene-formaldehyde condensation. Polym. Bull. 47, 493-499 (2002).
    • (2002) Polym. Bull. , vol.47 , pp. 493-499
    • Li, D.1    Kusunoki, T.2    Yamagishi, T.-A.3    Nakamoto, Y.4
  • 34
    • 0036933362 scopus 로고    scopus 로고
    • Two stereoisomers of C-unalkylated calix[4]resorcinarene and the conformation change
    • Li, D., Suzuki, T., Konishi, G.-I., Yamagishi, T.-A., Nakamoto, Y.: Two stereoisomers of C-unalkylated calix[4]resorcinarene and the conformation change. Polym. Bull. 48, 423-429 (2002).
    • (2002) Polym. Bull. , vol.48 , pp. 423-429
    • Li, D.1    Suzuki, T.2    Konishi, G.-I.3    Yamagishi, T.-A.4    Nakamoto, Y.5
  • 35
    • 33646336596 scopus 로고    scopus 로고
    • Scandium triflate-catalyzed cyclocondensation of 1, 3-dialkoxybenzenes with 1, 3, 5-trioxane Formation of resorcin[4]arenes and confused resorcin[4]arenes
    • Morikawa, O., Nagamatsu, Y., Nishimura, A., Kobayashi, K., Konishi, H.: Scandium triflate-catalyzed cyclocondensation of 1, 3-dialkoxybenzenes with 1, 3, 5-trioxane Formation of resorcin[4]arenes and confused resorcin[4]arenes. Tetrahedron Lett. 47, 3991-3994 (2006).
    • (2006) Tetrahedron Lett. , vol.47 , pp. 3991-3994
    • Morikawa, O.1    Nagamatsu, Y.2    Nishimura, A.3    Kobayashi, K.4    Konishi, H.5
  • 37
    • 0001606803 scopus 로고
    • Mesitylene-derived 1, 3-alternate [1.1.1.1]metacyclophanes
    • Pappalardo, S., Ferguson, G., Gallagher, J. F.: Mesitylene-derived 1, 3-alternate [1. 1. 1. 1]metacyclophanes. J. Org. Chem. 57, 7102-7109 (1992).
    • (1992) J. Org. Chem. , vol.57 , pp. 7102-7109
    • Pappalardo, S.1    Ferguson, G.2    Gallagher, J.F.3
  • 38
    • 0037060976 scopus 로고    scopus 로고
    • The template synthesis and complexation properties of methoxypyrogallo[4]arene
    • Iwanek, W., Urbaniak, M., Bocheńska, M.: The template synthesis and complexation properties of methoxypyrogallo[4]arene. Tetrahedron 58, 2239-2243 (2002).
    • (2002) Tetrahedron , vol.58 , pp. 2239-2243
    • Iwanek, W.1    Urbaniak, M.2    Bocheńska, M.3
  • 40
    • 0037899686 scopus 로고    scopus 로고
    • The synthesis of axially chiral resorcinarenes from resorcinol monoalkyl ethers and aldehydes dimethylacetals
    • Boxhall, J. Y., Bulman Page, P. C., Elsegood, M. R. J., Chan, Y., Heaney, H., Holmes, K. E., McGrath, M. J.: The synthesis of axially chiral resorcinarenes from resorcinol monoalkyl ethers and aldehydes dimethylacetals. Synlett 1002-1006 (2003).
    • (2003) Synlett , pp. 1002-1006
    • Boxhall, J.Y.1    Bulman Page, P.C.2    Elsegood, M.R.J.3    Chan, Y.4    Heaney, H.5    Holmes, K.E.6    McGrath, M.J.7
  • 41
    • 0038032750 scopus 로고    scopus 로고
    • First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by Lewis acid cyclization of a resorcinol monoalkyl ether
    • Klaes, M., Agena, C., Köhler, M., Inoue, M., Wada, T., Inoue, Y., Mattay, J.: First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by Lewis acid cyclization of a resorcinol monoalkyl ether. Eur. J. Org. Chem. 1404-1409 (2003).
    • (2003) Eur. J. Org. Chem. , pp. 1404-1409
    • Klaes, M.1    Agena, C.2    Köhler, M.3    Inoue, M.4    Wada, T.5    Inoue, Y.6    Mattay, J.7
  • 42
    • 15044359302 scopus 로고    scopus 로고
    • Determination of the absolute configuration of inherently chiral resorc[4]arenes
    • Klaes, M., Neumann, B., Stammler, H.-G., Mattay, J.: Determination of the absolute configuration of inherently chiral resorc[4]arenes. Eur. J. Org. Chem. 864-868 (2005).
    • (2005) Eur. J. Org. Chem. , pp. 864-868
    • Klaes, M.1    Neumann, B.2    Stammler, H.-G.3    Mattay, J.4
  • 43
    • 32144454170 scopus 로고    scopus 로고
    • New insights into the geometry of resorc[4]arenes: Solvent-mediated supramolecular conformational and chiroptical control
    • Schiel, C., Hembury, G. A., Borovkov, V. V., Klaes, M., Agena, C., Wada, T., Grimme, S., Inoue, Y., Mattay, J.: New insights into the geometry of resorc[4]arenes: solvent-mediated supramolecular conformational and chiroptical control. J. Org. Chem. 71, 976-982 (2006).
    • (2006) J. Org. Chem. , vol.71 , pp. 976-982
    • Schiel, C.1    Hembury, G.A.2    Borovkov, V.V.3    Klaes, M.4    Agena, C.5    Wada, T.6    Grimme, S.7    Inoue, Y.8    Mattay, J.9
  • 46
    • 33749432420 scopus 로고    scopus 로고
    • Synthesis and conformational properties of partially alkylated methylene-bridged resorc[4]arenes-study of the 'flip-flop' inversion
    • Dvořáková, H., Štursa, J., Čajan, M., Moravcová, J.: Synthesis and conformational properties of partially alkylated methylene-bridged resorc[4]arenes-study of the 'flip-flop' inversion. Eur. J. Org. Chem. 4519-4527 (2006).
    • (2006) Eur. J. Org. Chem. , pp. 4519-4527
    • Dvořáková, H.1    Štursa, J.2    Čajan, M.3    Moravcová, J.4
  • 53
    • 0033544765 scopus 로고    scopus 로고
    • Complexation of crown and diamond conformers of octamethoxyresorc[4]arene with strong electron acceptors
    • Urbaniak, M., Iwanek, W.: Complexation of crown and diamond conformers of octamethoxyresorc[4]arene with strong electron acceptors. Tetrahedron 55, 14459-14466 (1999).
    • (1999) Tetrahedron , vol.55 , pp. 14459-14466
    • Urbaniak, M.1    Iwanek, W.2
  • 56
    • 4644324791 scopus 로고    scopus 로고
    • Chiral recognition by resorcin[4]arene receptors: Intrinsic kinetics and dynamics
    • Tafi, A., Botta, B., Botta, M., Delle Monache, G., Filippi, A., Speranza, M.: Chiral recognition by resorcin[4]arene receptors: intrinsic kinetics and dynamics. Chem. Eur. J. 10, 4126-4135 (2004).
    • (2004) Chem. Eur. J. , vol.10 , pp. 4126-4135
    • Tafi, A.1    Botta, B.2    Botta, M.3    Delle Monache, G.4    Filippi, A.5    Speranza, M.6
  • 58
    • 33746191851 scopus 로고    scopus 로고
    • Flattened cone 2, 8, 14, 20-tetrakis(L-valinamido)[4]resorcinarene: An enantioselective allosteric receptor in the gas phase
    • Botta, B., Caporuscio, F., Subissati, D., Tafi, A., Botta, M., Filippi, A., Speranza, M.: Flattened cone 2, 8, 14, 20-tetrakis(L-valinamido)[4]resorcinarene: an enantioselective allosteric receptor in the gas phase. Angew. Chem. Int. Ed. 45, 2717-2720 (2006).
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 2717-2720
    • Botta, B.1    Caporuscio, F.2    Subissati, D.3    Tafi, A.4    Botta, M.5    Filippi, A.6    Speranza, M.7
  • 60
    • 34648828224 scopus 로고    scopus 로고
    • Gaseous- versus solution-phase recognition of some aromatic amino esters by 2, 8, 14, 20-tetrakis(L-valinamido)[4]resorcinarene
    • Botta, B., Delle Monache, G., Fraschetti, C., Nevola, L., Subissati, D., Speranza, M.: Gaseous- versus solution-phase recognition of some aromatic amino esters by 2, 8, 14, 20-tetrakis(L-valinamido)[4]resorcinarene. Int. J. Mass Spectrom. 267, 24-29 (2007).
    • (2007) Int. J. Mass Spectrom. , vol.267 , pp. 24-29
    • Botta, B.1    Delle Monache, G.2    Fraschetti, C.3    Nevola, L.4    Subissati, D.5    Speranza, M.6
  • 64
    • 53949105035 scopus 로고    scopus 로고
    • Modelling amphetamine/receptor interactions: A gas-phase study of complexes formed between amphetamine and some chiral amido[4]resorcinarenes
    • Botta, B., Tafi, A., Caporuscio, F., Botta, M., Nevola, L., D'Acquarica, I., Fraschetti, C., Speranza, M.: Modelling amphetamine/receptor interactions: a gas-phase study of complexes formed between amphetamine and some chiral amido[4]resorcinarenes. Chem. Eur. J. 14, 3585-3595 (2008).
    • (2008) Chem. Eur. J. , vol.14 , pp. 3585-3595
    • Botta, B.1    Tafi, A.2    Caporuscio, F.3    Botta, M.4    Nevola, L.5    D'Acquarica, I.6    Fraschetti, C.7    Speranza, M.8
  • 66
    • 33846021964 scopus 로고    scopus 로고
    • Novel tetramethoxy resorcinarene bis-crown ethers
    • Salorinne, K., Nissinen, M.: Novel tetramethoxy resorcinarene bis-crown ethers. Org. Lett. 8, 5473-5476 (2006).
    • (2006) Org. Lett. , vol.8 , pp. 5473-5476
    • Salorinne, K.1    Nissinen, M.2
  • 67
    • 38349018742 scopus 로고    scopus 로고
    • Alkali metal complexation properties of resorcinarene bis-crown ethers: Effect of the crown ether functionality and preorganization on complexation
    • Salorinne, K., Nissinen, M.: Alkali metal complexation properties of resorcinarene bis-crown ethers: effect of the crown ether functionality and preorganization on complexation. Tetrahedron 64, 1798-1807 (2008).
    • (2008) Tetrahedron , vol.64 , pp. 1798-1807
    • Salorinne, K.1    Nissinen, M.2
  • 69
    • 0001441691 scopus 로고    scopus 로고
    • The first enantioselective syntheses of axially chiral enantiomerically pure calix[4]resorcinarene derivatives
    • Bulman Page, P. C., Heaney, H., Sampler, E. P.: The first enantioselective syntheses of axially chiral enantiomerically pure calix[4]resorcinarene derivatives. J. Am. Chem. Soc. 121, 6751-6752 (1999).
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 6751-6752
    • Bulman page, P.C.1    Heaney, H.2    Sampler, E.P.3
  • 71
    • 38849201086 scopus 로고    scopus 로고
    • Cavity-extended inherently chiral resorcin[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers
    • Paletta, M., Klaes, M., Neumann, B., Stammler, H.-G., Grimme, S., Mattay, J.: Cavity-extended inherently chiral resorcin[4]arenes: synthesis and chiroptical properties of the cycloenantiomers. Eur. J. Org. Chem. 555-562 (2008).
    • (2008) Eur. J. Org. Chem. , pp. 555-562
    • Paletta, M.1    Klaes, M.2    Neumann, B.3    Stammler, H.-G.4    Grimme, S.5    Mattay, J.6


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