T.-M. Liu et al. / Tetrahedron 71 (2015) 8649e8660
8659
107.96, 110.55, 112.85, 113.15, 114.85, 117.38, 120.11, 124.24, 126.07,
127.00, 130.96, 131.78, 132.74, 137.74, 141.80, 148.86, 152.14, 154.70,
159.59, 159.61, 162.59, 164.83. Anal. Calcd for C65H94N2O6: C, 77.28;
H, 9.10; N, 1.73. Found: C, 77.05; H, 8.81; N, 2.51.
C65H94N2O6: C, 77.28; H, 10.08; N, 1.61. Found: C, 76.82; H, 10.32; N,
1.41.
4.8.1. (E)-4-(((3,4-Dibutoxyphenyl)imino)methyl)-3-hydroxyphenyl
4-(dodecyloxy) benzoate 2a (n¼4). Yellow solid, yield 85%. 1H NMR
4.7.4. (E)-4-(((3,4-Bis(decyloxy)phenyl)imino)methyl)-3-
(CDCl3):
d
0.86 (t, 3H, ꢀCH3, J¼5.68 Hz), 0.98 (m, 6H, ꢀCH2),
hydroxyphenyl 6-(dodecyloxy)-2-naphthoate 2b (n¼10). Yellow
1.00e1.25 (m, 12H, ꢀCH2), 1.49e1.52 (m, 6H, ꢀCH2), 1.82 (m, 6H,
ꢀCH2), 4.02 (m, 2H, ꢀOCH2), 6.79 (d, 1H, AreH, J¼8.30 Hz), 6.86 (m,
4H, AreH), 6.95 (d, 2H, AreH, J¼8.80 Hz), 7.38 (d, 2H, AreH, 8.11,
J¼8.45 Hz), 8.11 (d, 1H, AreH, J¼8.75 Hz), 8.58 (s, 1H, ꢀN]CeH),
solid yield 82%. 1H NMR (CDCl3):
d
0.88 (m, 9H, ꢀCH3), 1.28e1.45
(m, 40H, ꢀCH2),1.49 (m, 6H, ꢀCH2CH3),1.84 (m, 6H, ꢀCH2), 4.03 (m,
4H, ꢀOCH2), 4.11 (t, 2H, ꢀOCH2, J¼6.53 Hz), 6.88 (m, 4H, AreH), 6.93
(s, 1H, AreH), 7.14 (s, 1H, AreH), 7.40 (d, 1H, AreH, J¼8.31 Hz), 7.76
(d, 1H, AreH, J¼8.18 Hz), 7.86 (d, 1H, AreH, J¼9.01 Hz), 8.12 (d, 1H,
AreH, J¼8.48 Hz), 8.60 (s, 1H, ꢀN]CeH), 8.67 (s, 1H, AreH), 13.67
13.78 (s, 1H, AreOH). 13C NMR (CDCl3):
d 13.04, 13.91, 14.15, 19.26,
22.72, 26.00, 29.11, 29.38, 29.61, 29.66, 31.32, 31.36, 31.94, 68.37,
69.06, 69.31,107.43, 110.56, 112.97, 114.16, 114.35, 117.27, 121.24,
132.37, 132.86, 141.71, 148.56, 149.81, 149.81, 154.58, 162.48, 163.69,
164.43. Anal. Calcd for C65H94N2O6: C, 74.38; H, 8.58; N, 2.17. Found:
C, 74.21; H, 8.39; N, 1.92.
(s, 1H, AreOH). 13C NMR (CDCl3):
d 13.96, 22.61, 26.04, 26.06, 29.16,
29.28, 29.35, 29.38, 29.53, 29.58, 31.86, 68.32, 69.13, 69.89, 106.72,
107.90, 110.57, 112.89, 113.14, 114.81, 120.12, 124.22, 126.08, 127.61,
127.88, 139.97, 131.80, 132.78, 137.74, 141.67, 148.87, 150.14, 159.59,
162.62,164.83. Anal. Calcd for C65H94N2O6: C, 77.83; H, 9.45; N,1.62.
Found: C, 77.81; H, 9.53; N, 1.49.
4.8.2. (E)-4-(((3,4-Bis(octyloxy)phenyl)imino)methyl)-3-
hydroxyphenyl 4-(dodecyloxy) benzoate 2a (n¼8). Yellow solid,
yield 82%. 1H NMR (CDCl3):
d
0.85 (m, 9H, ꢀCH3, J¼5.68 Hz),
4.7.5. (E)-4-(((3,4-Bis(tetradecyloxy)phenyl)imino)methyl)-3-
1.28e1.34 (m, 32H, ꢀCH2), 1.46 (m, 6H, ꢀCH2), 1.82 (m, 6H, ꢀCH2),
4.01 (m, 6H, ꢀOCH2), 6.79 (d, 1H, AreH, J¼8.01 Hz), 6.86 (m, 4H,
AreH), 6.95 (d, 2H, AreH, J¼8.88 Hz), 7.38 (d, 1H, AreH, J¼8.43 Hz),
8.11 (d, 2H, AreH, J¼8.8 Hz), 8.58 (s, 1H, ꢀN]CeH), 13.77 (s, 1H,
hydroxyphenyl 6-(dodecyloxy)-2-naphthoate 2b (n¼14). Yellow
solid, yield 81%. 1H NMR (CDCl3):
d
0.87 (m, 9H, ꢀCH3), 1.26e1.36
(m, 56H, ꢀCH2),1.47 (m, 6H, ꢀCH2), 1.83 (m, 6H, ꢀCH2), 4.03 (m, 4H,
ꢀOCH2), 4.11 (t, 2H, ꢀOCH2, J¼6.45 Hz), 6.88 (m, 4H, AreH), 6.92 (s,
1H, AreH), 7.17 (s, 1H, AreH), 7.22 (d, 1H, AreH, J¼10.28 Hz), 7.40
(d, 1H, AreH, J¼8.43 Hz), 7.77 (d, 1H, AreH, J¼8.16 Hz), 7.86 (d, 1H,
AreH, J¼8.98 Hz), 8.12 (t, 1H, AreH, J¼8.58 Hz), 8.59 (s, 1H, ꢀN]
CeH), 8.67 (s, 1H, AreH), 13.60 (s, 1H, AreOH). 13C NMR (CDCl3):
AreOH). 13C NMR (CDCl3):
d 14.08, 14.17, 22.50, 22.72, 26.32, 28.28,
28.67, 30.02, 30.12, 30.38, 30.58, 30.62,30.66, 30.68, 31.94, 69.32,
69.34, 69.62, 07.38, 110.5, 122.82, 114.15, 117.36, 121.78, 133.36,
133.80, 140.44,149.57,149.80,154.63,159.72,162.52,163.32, 164.85.
Anal. Calcd for C65H94N2O6: C, 76.05; H, 9.44; N, 1.85. Found: C,
75.89; H, 9.15; N, 1.50.
d
0.93, 13.95, 22.60, 26.03, 26.04, 29.16, 29.27, 29.28, 29.33, 29.35,
29.38, 29.52, 29.54, 29.58, 29.60, 26.45, 31.87, 68.32, 69.63, 69.90,
106.72, 107.93, 110.55, 112.86, 113.14, 114.84, 117.37, 120.11, 124.23,
126.07, 127.00, 127.89, 130.97, 131.77, 132.74, 137.73, 141.78, 148.78,
148.86, 150.14, 154.71, 159.60, 162.60, 164.84. Anal. Calcd for
4.8.3. (E)-4-(((3,4-Bis(decyloxy)phenyl)imino)methyl)-3-
hydroxyphenyl 4-(dodecyloxy) benzoate 2a (n¼10). Yellow solid,
yield 75%. 1H NMR (CDCl3):
d
0.87 (m, 9H, ꢀCH3),1.25e1.34 (m, 40H,
C
65H94N2O6: C, 78.72; H, 10.01; N, 1.43. Found: C, 78.70; H, 9.98; N,
ꢀCH2),1.48 (m, 6H, ꢀCH2),1.82 (m, 6H, ꢀCH2), 4.03 (m, 6H, ꢀOCH2),
6.80 (d, 1H, AreH, J¼8.57 Hz), 6.86 (m, 4H, AreH), 6.95 (d, 2H,
AreH, J¼8.82 Hz), 7.37 (d, 1H, AreH, J¼8.44 Hz), 8.11 (d, 2H, AreH,
J¼8.80 Hz), 8.58 (s, 1H, ꢀN]CeH), 13.76 (s, 1H, AreOH). 13C NMR
2.00.
4.7.6. (E)-4-(((3,4-Bis(hexadecyloxy)phenyl)imino)methyl)-3-
hydroxyphenyl 6-(dodecyloxy)-2-naphthoate 2b (n¼16). Yellow
(CDCl3): d 14.14, 22.71, 26.00, 29.11, 29.28, 29.33, 29.38, 29.45,
solid, yield 81%. 1H NMR (CDCl3):
d
0.87 (m, 9H, ꢀCH3), 1.26e1.34
29.58, 29.61, 31.94, 37.69, 69.63, 107.40, 110.57, 112.98, 114.17, 117.25,
159.56, 162.49, 163.70, 164.40. Anal. Calcd for C65H94N2O6: C, 76.71;
H, 9.78; N, 1.72. Found: C, 76.58; H, 9.75; N, 1.59.
(m, 64H, ꢀCH2), 1.50 (m, 6H, ꢀCH2), 1.83 (m, 6H, ꢀOCH2), 4.03 (m,
4H, ꢀOCH2), 4.11 (t, 2H, ꢀOCH2, J¼6.53 Hz), 6.88 (m, 4H, AreH), 6.93
(s, 1H, AreH), 7.17 (s, 1H, AreH), 7.21 (d, 1H, AreH, J¼8.99 Hz), 7.40
(d, 1H, AreH, J¼8.44 Hz), 7.77 (d, 1H, AreH, J¼8.66 Hz), 7.87 (d, 1H,
AreH, J¼8.99 Hz), 8.10 (d, 1H, AreH, J¼8.45 Hz), 8.59 (s, 1H, ꢀN]
CeH), 8.67 (s, 1H, AreH), 13.65 (s, 1H, AreOH). 13C NMR (CDCl3):
4.8.4. (E)-4-(((3,4-Bis(tetradecyloxy)phenyl)imino)methyl)-3-
hydroxyphenyl 4-(dodecyloxy)benzoate 2a (n¼14). Yellow solid,
yield 86%. 1H NMR (CDCl3):
d
0.88 (m, 9H, ꢀCH3, J¼5.75 Hz),
d
13.95, 22.60, 26.04, 29.16, 29.27, 29.34, 29.36, 29.38, 29.52, 29.54,
1.27e1.36 (m, 56H, ꢀCH2), 1.47 (m, 6H, ꢀCH2), 1.82 (m, 6H, ꢀOCH2),
4.03 (m, 6H, ꢀOCH2), 6.80 (d, 1H, AreH, J¼8.35 Hz), 6.87 (m, 4H,
AreH), 6.95 (d, 2H, AreH, J¼8.74 Hz), 7.37 (d, 1H, AreH, J¼8.45 Hz),
8.11 (d, 2H, AreH, J¼8.73 Hz), 8.58 (s, 1H, ꢀN]CeH), 13.76 (s, 1H,
AreOH). 13C NMR (CDCl3): 13.96, 22.60, 25.95, 26.04, 29.10, 29.36,
29.39, 29.49, 29.52, 29.58, 29.61, 29.65, 31.88, 68.41, 69.62, 69.89,
107.92, 110.51, 112.87, 113.12, 114.42, 114.82, 117.26, 121.48, 132.23,
132.69, 141.79, 148.84, 150.13, 154.71, 159.60, 163.73, 164.25. Anal.
Calcd for C65H94N2O6: C, 77.79; H, 10.34; N, 1.51. Found: C, 77.64; H,
10.48; N, 1.46.
29.58, 29.60, 29.65, 31.87, 66.32, 69.64, 69.90, 106.73, 107.94, 110.56,
112.86, 113.14, 114.84, 117.37, 120.11, 124.24, 126.07, 127.00, 130.96,
131.78, 132.74, 137.73, 141.76, 148.86, 150.14, 154.71, 159.60, 162.60,
164.83. Anal. Calcd for C65H94N2O6: C, 79.10; H, 10.25; N, 1.36.
Found: C, 78.96; H, 10.26; N, 1.22.
4.8. (E)-4-(((3,4-Bis(dodecyloxy)phenyl)imino)methyl)-3-
hydroxyphenyl 4-(dodecyloxy)benzoate 2a (n[12)
Yield 78%. 1H NMR (CDCl3):
d
0.87 (m, 9H, ꢀCH3), 1.26e1.35 (m,
48H, ꢀCH2), 1.46 (m, 6H, ꢀCH2), 1.81 (m, 6H, ꢀCH2), 4.03 (m, 6H,
ꢀOCH2), 6.80 (d, 1H, AreH, J¼8.41 Hz), 6.86 (m, 4H, AreH), 6.95 (d,
2H, AreH, J¼8.81 Hz), 7.37 (d, 1H, AreH, J¼8.42 Hz), 8.11 (d, 2H,
4.8.5. (E)-4-(((3,4-Bis(hexadecyloxy)phenyl)imino)methyl)-3-
hydroxyphenyl 4-(dodecyloxy)benzoate 2a (n¼16). Yellow solid,
yield 88%. 1H NMR (CDCl3):
d
0.86 (m, 9H, ꢀCH3),1.24e1.34 (m, 64H,
AreH, J¼8.80 Hz), 8.57 (s, 1H, ꢀN]CeH), 13.76 (s, 1H, AreOH). 13
C
ꢀCH2),1.46 (m, 6H, ꢀCH2),1.80 (m, 6H, ꢀCH2), 4.01 (m, 6H, ꢀOCH2),
6.79 (d, 1H, AreH, J¼8.51 Hz), 6.84 (m, 4H, AreH), 6.88 (d, 2H,
AreH, J¼8.35 Hz), 7.39 (d, 1H, AreH, J¼8.50 Hz), 8.11 (d, 2H, AreH,
J¼8.89 Hz), 8.59 (s, 1H, ꢀN]CeH), 13.77 (s, 1H, AreOH). 13C NMR
NMR (CDCl3):
d 13.94, 2.59, 22.70, 25.94, 26.02, 26.16, 29.09, 29.26,
29.28, 29.37, 29.48, 29.51, 29.63, 29.68, 31.86, 31.93, 68.24, 68.42,
69.63, 69.90, 106.44, 107.93, 110.51, 110.65, 112.29, 113.13, 114.43,
114.84, 120.15, 126.11, 127.01, 131.00, 131.82, 132.30, 132.67, 141.80,
148.83, 150.12, 159.62, 162.54, 163.41, 163.74, 164.11. Anal. Calcd for
(CDCl3): d 14.14, 22.71, 25.99, 26.05, 29.10, 29.27, 29.31, 29.37, 29.39,
29.46, 29.57, 29.60, 29.67, 29.69, 29.74, 31.94, 68.37, 69.36, 69.62,