988
Z.-Q. Shi et al.
N-[N-(2-Butyl-phthalimide-4-yl)aminocarbonylmethoxy]-calix[4](aza)mono-
crown 6b: white solid, yield 55%, mp (.2508C decomposed);
1
IR (KBr, cm21): 3395, 3317, 1735, 1713, 1662; H NMR (CDCl3, d ppm):
10.05 (s, 1H, CONH), 9.12 (t, 2H, J ¼ 5.5 Hz), 8.26 (s, 1H, ArH), 8.21
(d, 1H, J ¼ 8 Hz, ArH), 8.04 (s, 2H, OH), 7.76 (d, 1H, J ¼ 8 Hz, ArH),
7.13 (d, 4H, J ¼ 8 Hz, ArHmeta), 6.99 (d, 4H, J ¼ 8 Hz, ArHmeta), 6.86
(t, 2H, J ¼ 8 Hz, ArHp), 6.78 (t, 2H, J ¼ 8 Hz, ArHp), 4.66 (s, 4H,
OCH2CO), 4.16 (d, 4H, J ¼ 13.5 Hz, ArCH2Ar), 3.64 (m, 2H, NCH2CH2),
3.62 (m, 4H, CONHCH2), 3.54 (d, 4H, J ¼ 13.5 Hz, ArCH2Ar), 3.39
(s, 2H, NCH2CO), 3.02 (m, 4H, NCH2), 1.64 (m, 2H, NCH2CH2), 1.34
(m, 2H, CH2CH3), 0.93 (t, 3H, J ¼ 7 Hz, CH3). 13C NMR (CDCl3): d 13.89
(1CH3), 20.31 (1CH2), 30.91 (1CH2), 31.91 (4ArCH2Ar), 37.99
(1 NCH2CH2CH2CH3), 40.64 (2CONHCH2), 54.80 (2 NCH2), 61.96
(1NCH2CO), 75.27 (2CH2O), [114.22 (1C), 121.33 (2C), 123.72 (1C),
124.41 (1C), 126.55 (1C), 127.19 (2C), 127.75 (4C), 129.44 (4C), 130.05
(4C), 132.79 (4C), 133.85 (1C), 144.67 (1C), 150.96 (2C), 151.96 (2C)]
(aromatic 30C), 168.50 (hetero 2C), 168.56 (1 NCH2CO), 169.37
(2COCH2). ESI-MS m/z 866.4 (M þ H)þ (calcd. for C50H51N5O9 865.4).
Anal. calcd. for C50H51N5O9: C, 69.35; H, 5.94. Found: C, 69.41; H, 5.91.
N-[N-(2-Octyl-phthalimide-4-yl)aminocarbonylmethoxy]-calix[4](aza)mono-
crown 6c: white solid, yield 64%, mp (.2508C decomposed); IR (KBr,
1
cm21): 3361, 3325, 1767, 1708, 1657; H NMR (CDCl3, d ppm): 10.05
(s, 1H, CONH), 9.12 (t, 2H, J ¼ 5.5 Hz), 8.26 (s, 1H, ArH), 8.21 (d, 1H,
J ¼ 8 Hz, ArH), 8.04 (s, 2H, OH), 7.77 (d, 1H, J ¼ 8 Hz, ArH), 7.13
(d, 4H, J¼ 8 Hz, ArHmeta), 6.99 (d, 4H, J ¼ 8 Hz, ArHmeta), 6.85 (t, 2H,
J ¼ 8 Hz, ArHp), 6.78 (t, 2H, J ¼ 8 Hz, ArHp), 4.66 (s, 4H, OCH2CO), 4.13
(d, 4H, J ¼ 13.5 Hz, ArCH2Ar), 3.64 (m, 2H, NCH2CH2), 3.63 (m, 4H,
CONHCH2), 3.54 (d, 4H, J ¼ 13.5 Hz, ArCH2Ar), 3.39 (s, 2H, NCH2CO),
3.02 (m, 4H, NCH2), 1.65 (m, 2H, NCH2CH2), 1.34–1.21 [m, 10H,
(CH2)5CH3], 0.86 (t, 3H, J¼ 7 Hz, CH3). 13C NMR (CDCl3): d 14.31
(1CH3), 22.85 (1CH2), 27.11 (1CH2), 28.92 (1CH2), 29.39 (1CH2), 29.40
(1CH2), 31.90 (4ArCH2Ar), 32.01 (1CH2), 38.28 (1 NCH2CH2CH2), 40.63
(2CONHCH2), 54.81 (2 NCH2), 61.96 (1NCH2CO), 75.27 (2CH2O),
[114.23 (1C), 121.33 (2C), 123.74 (1C), 124.41 (1C), 126.55 (1C), 127.19
(2C), 127.75 (4C), 129.44 (4C), 130.05 (4C), 132.79 (4C), 133.86 (1C),
144.64 (1C), 150.96 (2C), 151.96 (2C)] (aromatic 30C), 168.50 (hetero
2C), 168.54 (1 NCH2CO), 169.38 (2COCH2). ESI-MS m/z 922.4(M þ H)þ
(calcd. for C54H59N5O9 921.4). Anal. calcd. for C54H59N5O9: C, 70.34; H,
6.45. Found: C, 70.38; H, 6.43.
N-[N-(2-Benzyl-phthalimide-4-yl)aminocarbonylmethoxy]-calix[4](aza)mono-
crown 6d: white solid, yield 51%, mp (.2508C decomposed); IR (KBr,
1
cm21): 3352, 3310, 1766, 1712, 1670; H NMR (CDCl3, d ppm): 10.06
(s, 1H, CONH), 9.11 (t, 2H, J ¼ 5.5 Hz), 8.27 (s, 1H, ArH), 8.22 (d, 1H,