Synthesis and structure of new cyclophanes containing benzofuran and benzene rings-Reference-Cited by-同舟云学术

Synthesis and structure of new cyclophanes containing benzofuran and benzene rings

Published:2000-02 Issue:9 Volume:41 Page:1393-1396
ISSN:0040-4039
Container-title:Tetrahedron Letters
language:en
Short-container-title:Tetrahedron Letters

Author:

Park Kwanghee Koh,Seo Hyeonjin,Kim Jin-Gyu,Suh Il-Hwan

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference13 articles.

1. Breitenbach, J.; Boosfeld, J.; Vogtle, F. In Comprehensive Supramolecular Chemistry; Vogtle, F., Ed.; Elsevier Science, 1996; Vol. 2, pp. 29–67.

2. Vogtle, F. Cyclophane Chemistry; Wiley: Chichester, 1993.

3. Compound 1: mp 175–176°C; 1H NMR (DMSO-d6) δ 5.21 (s, 4H, -OCH2-C6H4-CH2O-), 6.65–6.58 (m, 4H, two Ar-H ortho to -OH and two Ar-H para to -OH), 7.7–7.4 (m, 16H, Ar-H), 11.95 (broad s, 2H).

4. Compound 2: mp 172°C; 1H NMR (CDCl3) δ 1.0–0.9 (m, 4H, -OCH2CH2(CH2)2CH2CH2O-), 1.35–1.2 (m, 4H, -OCH2CH2-(CH2)2CH2CH2O-), 3.59 (t, J=6 Hz, 4H, -OCH2(CH2)4CH2O-), 5.27 (s, 4H, -OCH2-C6H4-CH2O-), 6.26 (d, J=2 Hz, 2H, Ar-H ortho to -O(CH2)6-), 6.71 (dd, J=8 and 2 Hz, 2H, Ar-H para to -O(CH2)6-), 7.5-7.3 (m, 12H, Ar-H), 7.70 (dd, J=7 and 2 Hz, 4H, Ar-H ortho to CO in two benzoyl groups); 13C NMR (CDCl3) δ 23.6, 27.0, 67.8, 69.8, 99.1, 109.3, 121.7, 126.7, 127.9, 129.3, 131.9, 132.1, 136.8, 139.0, 158.9, 162.0, 195.8; mass (EI) 104 (100), 105 (96), 215 (26), 316 (42), 317 (90), 508 (53), 612 (99, M+), 613 (43); anal. calcd for C40H36O6: C, 78.41; H, 5.92. Found: C, 78.34; H, 5.60.

5. Compound 3: mp 220–223°C; 1H NMR (CDCl3) δ 0.9–0.8 (m, 8H, -OCH2CH2(CH2)2CH2CH2O-), 1.35–1.2 (m, 8H, -OCH2CH2(CH2)2CH2CH2O-), 3.72 (t, J=6 Hz, 8H, -OCH2(CH2)4CH2O-), 5.14 (s, 8H, -OCH2-C6H4-CH2O-), 6.51 (d, J=2 Hz, 4H, Ar-H ortho to -O(CH2)6-), 6.62 (dd, J=8 and 2 Hz, 4H, Ar-H para to -O(CH2)6-), 7.5–7.3 (m, 24 H, Ar-H), 7.71 (dd, J=7 and 2 Hz, 8H, Ar-H ortho to CO in four benzoyl groups); 13C NMR (CDCl3) δ 24.7, 28.3, 67.8, 69.9, 100.3, 111.5, 122.2, 127.8, 127.9, 129.4, 132.0, 132.2, 136.5, 139.3, 159.0, 162.4, 198.0; mass (positive ion FAB) 1225.50 (M++H+); anal. calcd for C80H72O12: C, 78.41; H, 5.92. Found: C, 78.67; H, 5.95.

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