Med Chem Res
residue was chromatographed on silica gel column using
toluene-ethyl acetate (8:2) mixture as eluent for separation
of reaction products 3a–f.
(s, 5H), 4.57 (t, J = 1.6Hz, 2H), 4.92 (t, J = 2Hz, 2H), 6.92
(d, J = 8.4Hz 1H), 6.99 (d, J = 15.6Hz, 1H), 7.15–7.26
(m, 2H), 7.75 (d, J = 15.6Hz, 1H); 13C NMR (50 MHz,
CDCl3): δ 22, 56.2, 69.7, 70, 71.4, 72.5, 80.8, 111.6, 120.9,
122.2, 128.2, 129, 141, 149.6, 150.4, 192.9 (CO). Anal.:
calcd. for C23H24FeO3 (404.280): C, 68.33; H, 5.98; Fe,
13.81; O, 11.87. Found: C, 67.31; H, 5.95.
1-Ferrocenyl-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (3a)
Cinnabar red crystals; m.p. 148–149 °C; yield 78 %;
IR (cm−1): 1648, 1586, 1517, 1263, 1081; 1H NMR
(200 MHz, CDCl3): δ 3.95 (d, J = 6.8 Hz, 6H), 4.22 (s, 5H),
4.58 (t, J = 2Hz, 2H), 4.92 (t, J = 2Hz, 2H), 6.91 (d, J =
8.4Hz 1H), 6.99 (d, J = 15.6Hz, 1H), 7.14–7.27 (m, 2H),
7.76 (d, J = 15.6Hz, 1H); 13C NMR (50 MHz, CDCl3):
δ 55.9, 69.7, 70, 72.5, 80.7, 110.6, 111.3, 121, 122.4,
128.2, 140.9, 149.2, 151.1, 192.8 (CO). Anal.: calcd. for
C21H20FeO3 (376.227): C, 67.04; H, 5.36; Fe, 14.84; O,
12.76. Found: C, 66.10; H, 5.30.
1-Ferrocenyl-3-(4-butoxy-3-methoxyphenyl)prop-2-en-1-
one (3e)
Cinnabar red crystals; m.p. 128 °C; yield 68 %; IR (cm−1):
1651, 1592, 1511, 1264, 1077; 1H NMR (200 MHz,
CDCl3): δ 0.99 (t, J = 7.4Hz, 3H), 1.45–1.57 (m, 2H),
1.76–1.89 (m, 2H), 3.95 (s, 3H), 4.08 (t, J = 6.8Hz, 2H),
4.21 (s, 5H), 4.57 (t, J = 2Hz, 2H), 4.92 (t, J = 2Hz, 2H),
6.91 (d, J = 8.2Hz 1H), 6.99 (d, J = 15.6Hz, 1H), 7.14–7.26
(m, 2H), 7.75 (d, J = 15.6Hz, 1H); 13C NMR (50 MHz,
CDCl3): δ 13.8, 31.1, 56.2, 68.7, 69.7, 70, 72.5, 80.8, 111.2,
112.7, 120.8, 122.4, 127.9, 141, 149.6, 150.8, 192.9 (CO).
Anal.: calcd. for C24H26FeO3 (418.306): C, 68.91; H, 6.26;
Fe, 13.35; O, 11.47. Found: C, 68.16; H, 6.23.
1-Ferrocenyl-3-(4-ethoxy-3-methoxyphenyl)prop-2-en-1-
one (3b)
Cinnabar red crystals; m.p. 155–156 °C; yield 85 %; IR
(cm−1): 1650, 1588, 1513, 1267, 1076; 1H NMR (200 MHz,
CDCl3): δ 1.49 (t, J = 7Hz, 3H), 3.96 (s, 3H), 4.16 (q, J =
7.2Hz, 2H), 4.21 (s, 5H), 4.57 (t, J = 1.8Hz, 2H), 4.92
(t, J = 1.8Hz, 2H), 6.90 (d, J = 8.4Hz 1H), 6.99 (d, J =
15.6Hz, 1H), 7.14–7.27 (m, 2H), 7.75 (d, J = 15.6Hz, 1H);
13C NMR (50 MHz, CDCl3): δ 14.7, 56.1, 64.4, 69.6, 70,
72.5, 80.8, 110.9, 112.5, 120.9, 122.4, 128, 141, 149.5,
150.5, 192.9 (CO). Anal.: calcd. for C22H22FeO3 (390.253):
C, 67.71; H, 5.68; Fe, 14.31; O, 12.30. Found: C, 66.61;
H, 5.61.
1-Ferrocenyl-3-(4-benzyloxy-3-methoxyphenyl)prop-2-en-
1-one (3f)
Cinnabar red crystals; m.p. 135–136 °C; yield 67 %;
IR (cm−1): 1650, 1591, 1515, 1262, 1084; 1H NMR
(200 MHz, CDCl3): 3.97 (s, 3H), 4.20 (s, 5H), 4.57 (t, J =
2Hz, 2H), 4.91 (t, J = 2Hz, 2H), 5.21 (s, 2H), 6.91 (d, J =
8.2Hz, 1H), 6.98 (d, J = 15.6Hz, 1H), 7.15–7.43 (m, 7H),
7.74 (d, J = 15.6Hz, 1H); 13C NMR (50 MHz, CDCl3):
δ 56.1, 69.6, 70, 70.9, 72.5, 80.7, 111.3, 113.7, 121.1,
122.1, 127.2, 127.9, 128.5, 128.6, 136.6, 140.9, 149.8,
150.2, 192.8 (CO). Anal.: calcd. for C27H24FeO3 (452.323):
C, 71.69; H, 5.35; Fe, 12.35; O, 10. 61. Found: C, 70.61;
H, 5.32.
1-Ferrocenyl-3-(3-methoxy-4-propoxyphenyl)prop-2-en-1-
one (3c)
Cinnabar red crystals; m.p. 104–105 °C; yield 79 %;
IR (cm−1): 1647, 1586, 1515, 1258, 1079; 1H NMR
(200 MHz, CDCl3): δ 1.06 (t, J = 7.6Hz, 3H), 1.80–1.98
(m, 2H), 3.95 (s, 3H), 4.03 (t, J = 6.8Hz, 2H), 4.21 (s, 5H),
4.57 (t, J = 1.6Hz, 2H), 4.92 (t, J = 2Hz, 2H), 6.90 (d, J =
8.4Hz 1H), 6.99 (d, J = 15.6Hz, 1H), 7.14–7.27 (m, 2H),
7.75 (d, J = 15.6Hz, 1H); 13C NMR (50 MHz, CDCl3):
δ 10.3, 22.3, 56.2, 69.6, 70, 70.5, 72.5, 80.8, 111.2, 112.7,
120.8, 122.4, 127.9, 141, 149.6, 150.8, 192.8 (CO). Anal.:
calcd. for C23H24FeO3 (404.280): C, 68.33; H, 5.98; Fe,
13.81; O, 11.87. Found: C, 67.51; H, 5.93.
X-ray crystallography and structural comparisons of 3b
and 3e
Crystal data and experimental details for 3b and 3e com-
pounds are summarized in Table 2. Single-crystal diffrac-
tion data were collected at room temperature on an Agilent
Gemini S diffractometer equipped with Mo Kα radiation
(λ = 0.71073 Å). Data integration and scaling of the
reflections were performed using the CRYSALIS software
(Agilent Technologies, 2013) with multi-scan absorption
corrections applied using SCALE3 ABSPACK (Agilent
Technologies, 2013). Crystal structure was solved by direct
methods, using SIR2002 (Burla et al., 2003) and refined
using SHELXL97 (Sheldrick, 2008) program both incor-
porated in WinGX (Farrugia, 1999) program package.
1-Ferrocenyl-3-(4-isopropoxy-3-methoxyphenyl)prop-2-en-
1-one (3d)
Cinnabar red crystals; m.p. 114 °C; yield 59 %; IR (cm−1):
1653, 1590, 1508, 1264, 1074; 1H NMR (200 MHz,
CDCl3): δ 1.41 (d, J = 6.2Hz, 6H), 3.94 (s, 3H), 4.21