New calixcrown-type ionophores derived from all possible regioisomers of rigid calix[4]arene

Synlett

Volumn , Issue 1, 2000, Pages 41-44

  Okada, Yukihiro ^a   Mizutani, Manabu ^a   Ishii, Fuyuhiko ^a   Nishimura, Jun ^a  

^a GUNMA UNIVERSITY   (Japan)

Author keywords

Alkali metal; Calixarene; Cyclophane; Ion extraction; Ionophore; Regioisomer

Indexed keywords

ALKALI METAL; CALIXARENE; CYCLOPHANE; IONOPHORE; METAL ION;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; EXTRACTION; ISOMER; SYNTHESIS;

EID: 0033958754     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (10)

1. Calixarenes 50th Anniversary; Vicens, J.; Asfari, Z; Harrowfield, J. M. Eds.; Kluwer: Dordrecht, 1994.
2. Böhmer, V. Angew. Chem. Int. Ed. Engl. 1995, 34, 713.
3. Okada, Y.; Mizutani, M.; Ishii, F.; Nishimura, J. Tetrahedron Lett. 1997, 38, 9013.
4. Okada, Y.; Mizutani, M.; Ishii, F.; Nishimura, J. Tetrahedron Lett. 1998, 39, 8461.
5. Okada, Y.; Mizutani, M.; Ishii, F.; Nishimura, J. Tetrahedron Lett. 1999, 40, 1353.
6. Okada, Y.; Ishii, F.; Kasai, Y.; Nishimura, J. Chem. Lett. 1992, 755.
7. Okada, Y.; Ishii, F.; Kasai, Y.; Nishimura, J. Tetrahedron Lett. 1993, 54, 1971.
8. Okada, Y.; Kasai, Y.; Ishii, F.; Nishimura, J. J. Chem. Soc., Chem. Commun. 1993, 976.
9. Okada, Y.; Kasai, Y.; Nishimura, J. Tetrahedron Lett. 1995, 36, 555.
10. 3 δ (intensity, multiplicity, J in Hz). 2: -0.13 (2H, m), 0.60 (2H, m), 1.25 (2H, m), 1.29 (6H, d, 6.1), 1.40 (2H, m), 1.48 (6H, d, 6.1), 1.75 (4H, m), 2.20-2.60 (12H, m), 2.69 (4H, m), 3.06 (1H, d, 13), 3.09 (1H, d, 13), 3.84 (1H, d, 13), 3.97 (2H, q, 6.1), 4.36 (4H, q-like), 4.40 (1H, d, 13), 6.70 (2H, d, 2.0), 6.82 (2H, d, 2.0), 7.02 (2H, d, 2.0), 7.12 (2H, d, 2.0), 8.42 (2H, s). 3: -0.17 (2H, m), 0.53 (2H, m), 1.25 (2H, m), 1.32 (6H, d, 7.5), 1.35 (2H, m), 1.45 (6H, d, 7.5), 1.71 (2H, m), 1.77 (2H, m), 1.90 (2H, m), 2.26 (4H, m), 2.42 (2H, m), 2.69 (6H, m), 2.87 (2H, q-like), 3.17 (2H, d, 14), 3.83 (2H, d, 14), 4.06 (2H, q, 7.5), 4.32 (2H, t-like), 4.57 (2H, q-like), 6.61 (2H, d, 2.0), 6.66 (2H, d, 2.0), 6.96 (2H, d, 2.0), 7.17 (2H, d, 2.0), 7.64 (2H, s). 4: -0.24 (1H, m), -0.07 (1H, m), 0.49 (1H, m), 0.62 (1H, m), 0.90 (4H, m), 1.38 (6H, d, 6.1), 1.49 (6H, d, 6.1), 1.71 (2H, m), 1.80 (2H, m), 2.20-2.57 (12H, m), 2.69 (4H, m), 3.17 (2H, d, 13), 3.87 (2H, d, 13), 4.22 (2H, q, 6. 1), 4.40 (2H, m), 4.65 (2H, m), 6.53 (2H, d, 2.0), 6.77 (2H, d, 2.0), 6.98 (2H, d, 2.0), 7.14 (2H, d, 2.0), 7.33 (2H, s). 6a: -0.02 (2H, m), 0.72 (2H, m), 1.25 (6H, d, 7.0), 1.28 (6H, d, 7.0), 1.43 (4H, m), 1.80 (4H, m), 2.21-2.52 (8H, m), 2.58 (4H, m), 2.70 (4H, m), 2.95 (1H, d, 13), 3.02 (1H, d, 13), 3.81 (2H, q, 7.0), 3.82-4.07 (10H, m), 4.36 (4H, m), 4.37 (1H, d, 13), 4.42 (1H, d, 13), 4.51 (2H, q-like), 6.91 (2H, d, 2.0), 6.97 (2H, d, 2.0), 7.05 (2H, d, 2.0), 7.10 (2H, d, 2.0). 6b: -0.02 (2H, m), 0.75 (2H, m), 1.26 (6H, d, 7.0), 1.36 (6H, d, 7.0), 1.46 (4H, m), 1.78 (4H, m), 2.34-2.62 (12H, m), 2.66 (4H, m), 2.92 (1H, d, 13), 2.94 (1H, d, 13), 3.40 (4H, m), 3.86 (8H, m), 3.89 (2H, q, 7.0), 4.10 (4H, m), 4.38 (2H, m), 4.42 (1H, d, 13), 4.47 (1H, d, 13), 4.53 (2H, t-like), 6.89 (2H, d, 2.0), 6.92 (2H, d, 2.0), 7.03 (2H, d, 2.0), 7.08 (2H, d, 2.0). 6c: 0.00 (2H, m), 0.76 (2H, m), 1.25 (6H, d, 6.0), 1.33 (6H, d, 6.0), 1.50 (4H, m), 1.78 (4H, m), 2.34-2.54 (12H, m), 2.70 (4H, m), 2.91 (1H, d, 13), 2.92 (1H, d, 13), 3.43 (4H, m), 3.74-4.09 (16H, m), 3.82 (2H, q, 6.0), 4.37 (2H, m), 4.43 (1H, d, 13), 4.44 (1H, d, 13), 4.55 (2H, m), 6.88 (2H, d, 2.0), 6.92 (2H, d, 2.0), 7.03 (2H, d, 2.0), 7.08 (2H, d, 2.0). 7a: 0.37 (2H, m), 0.97 (2H, m), 1.23 (6H, d, 7.0), 1.24 (2H, m), 1.35 (6H, d, 7.0), 1.74 (4H, m), 1.82 (2H, m), 2.18 (4H, m), 2.39 (2H, m), 2.50-2.82 (10H, m), 2.96 (2H, d, 13), 3.09 (2H, m), 3.36 (2H, m), 3.72 (2H, m), 3.78 (2H, q, 7.0), 4.08 (4H, m), 4.28 (2H, d, 13), 4.28 (2H, m), 4.42 (2H, m), 4.56 (2H, q-like), 6.65 (2H, d, 2.0), 6.95 (2H, d, 2.0), 6.97 (2H, d, 2.0), 7.22 (2H, d, 2.0). 7b: 0.03 (2H, m), 0.77 (2H, m), 1.25 (6H, d, 7.0), 1.34 (6H, d, 7.0), 1.34 (2H, m), 1.58 (2H, m), 1.78 (4H, m), 2.20-2.78 (16H, m), 2.94 (2H, d, 13), 3.44 (2H, m), 3.57 (2H, m), 3.70-3.92 (8H, m), 3.81 (2H, q, 7.0), 4.14 (4H, m), 4.38 (2H, d, 13), 4.43 (4H, m), 6.85 (2H, d, 2.0), 6.96 (2H, d, 2.0), 7.03 (2H, d, 2.0), 7.08 (2H, d, 2.0). 7c: 0.03 (2H, m), 0.78 (2H, m), 1.26 (6H, t, 7.0), 1.37 (6H, d, 7.0), 1.46 (2H, m), 1.56 (2H, m), 1.79 (4H, m), 2.24-2.76 (16H, m), 2.95 (2H, d, 14), 3.57 (2H, m), 3.64-4.16 (18H, m), 3.80 (2H, q, 7.0), 4.40 (2H, d, 14), 4.44 (2H, m), 4.57 (2H, q-like), 6.92 (2H, d, 2.0), 6.93 (2H, d, 2.0), 7.02 (2H, d, 2.0), 7.09 (2H, d, 2.0). 8a: -0.18 (1H, m), 0.00 (1H, m), 0.66 (2H, m), 1.23 (6H, d, 7.0), 1.30 (2H, m), 1.34 (6H, d, 7.0), 1.43 (2H, m), 1.79 (4H, m), 2.15-2.58 (12H, m), 2.70 (4H, m), 2.96 (2H, d, 13), 3.34 (2H, m), 3.55 (2H, m), 3.80 (2H, q, 7.0), 3.85 (2H, m), 4.00 (4H, t-like), 4.13 (2H, m), 4.36 (2H, m), 4.39 (2H, d, 13), 4.79 (2H, m), 6.91 (2H, d, 2.0), 6.95 (2H, d, 2.0), 7.07 (2H, d, 2.0), 7.08 (2H,d, 2.0). 8b: -0.02 (1H, m), 0.06 (1H, m), 0.73 (2H, m), 1.28 (6H, d, 7.0), 1.30 (6H, d, 7.0), 1.46 (4H, m), 1.78 (4H, m), 2.32-2.56 (12H, m), 2.66 (4H, m), 2.93 (2H, d, 13), 3.16 (2H, m), 3.72 (2H, m), 3.80-4.12 (12H, m), 3.83 (2H, q, 7.0), 4.37 (2H, m), 4.40 (2H, d, 13), 4.68 (2H, t-like), 6.87 (2H, d, 2.0), 6.91 (2H, d, 2.0), 7.07 (2H, d, 2.0), 7.08 (2H, d, 2.0). 8c: 0.00 (1H, m), 0.06 (1H, m), 0.78 (2H, m), 1.29 (6H, d, 6.1), 1.31 (6H,d,6.1), 1.46 (4H, m), 1.79 (4H, m), 2.34-2.56 (12H, m), 2.70 (4H, m), 2.94 (2H, d, 13), 3.12 (2H, m), 3.66 (2H, m), 3.70-4.10 (16H, m), 3.81 (2H, q, 6.1), 4.36 (2H, m), 4.40 (2H, d, 13), 4.63 (2H, bt), 6.86 (2H, d, 2.0), 6.90 (2H, d, 2.0), 7.06 (2H, d, 2.0), 7.07 (2H, d, 2.0).