ALAVI ET AL.
7
134.65, 126.86, 126.40, 124.33, 117.89, 115.81, 34.47. MS (EI, 70 eV):
m/z = 179 [M+]; Anal. calcd for C9H9NO3: C, 60.33; H, 5.06; N. 7.82.
Found: C, 60.12; H, 5.00; N. 7.78.
70 eV): m/z = 274 [M+]; Anal. calcd for C18H26O2: C, 78.79; H, 9.55.
Found: C, 78.54; H, 9.45.
4.21
|
2,6-diallyl-4-(heptyloxy)phenol (43)
4.16
|
2,6-diallylphenol (37)
Yellow oil, 1H NMR (301 MHz, Chloroform-d)
δ 6.50 (s, 2H),
Colorless oil, 1H NMR (301 MHz, Chloroform-d) δ 7.10 (d, J = 7.5 Hz,
2H), 6.93 (t, J = 6.5 Hz, 1H), 6.18–6.04 (m, 2H), 5.27–5.24 (m, 2H),
5.26 (s, 1H), 5.21 (t, J = 1.5 Hz, 2H), 3.50 (d, J = 6.4 Hz, 4H); 13C NMR
(76 MHz, Chloroform-d) δ 152.70, 136.67, 128.78, 125.72, 120.72,
116.44, 35.35. MS (EI, 70 eV): m/z = 174 [M+]; Anal. calcd for
6.07–5.84 (m, 2H), 5.15–5.02 (m, 4H), 4.67 (s, 1H), 3.80 (t, J = 6.6 Hz,
2H), 3.30 (d, J = 6.4 Hz, 4H), 1.70–1.62 (m, 2H), 1.43–1.17 (m, 8H),
0.82 (t,, J = 6.6 Hz, 3H); 13C NMR (76 MHz, Chloroform-d) δ 152.96,
146.29, 136.47, 126.76, 116.41, 114.52, 68.45, 35.52, 31.83, 29.47,
29.13, 26.07, 22.65, 14.14. MS (EI, 70 eV): m/z = 288 [M+]; Anal.
calcd for C19H28O2: C, 79.12; H, 9.79. Found: C, 78.69; H, 9.12.
C
12H14O: C, 82.72; H, 8.10. Found: C, 82.72; H, 8.09.
4.17
|
2,6-diallyl-4-chlorophenol (38)
4.22
|
3,5-diallyl-4-hydroxybenzaldehyde (44)
Yellowish oil,1H NMR (301 MHz, Chloroform-d) δ 6.90 (s, 2H),
5.99–5.79 (m, 2H), 5.11–5.09 (m, 2H), 5.07–5.04 (m, 2H), 5.03 (s, 1H),
3.27 (d, J = 6.4 Hz, 4H); 13C NMR (76 MHz, Chloroform-d) δ 151.22,
135.73, 128.28, 127.42, 117.08, 116.26, 35.05. MS (EI, 70 eV): m/
z = 208 [M+]; Anal. calcd for C12H13ClO: C, 69.07; H, 6.28. Found: C,
69.10; H, 6.27.
Yellow powder (mp: 53–55ꢀC),1H NMR (301 MHz, Chloroform-d) δ
9.76 (s, 1H), 7.51 (s, 2H), 6.03–5.91 (m, 2H), 5.90 (s, 1H), 5.15 (m, 2H),
5.11 (dq, J = 7.9, 1.4 Hz, 1H), 3.40 (d, J = 6.4 Hz, 4H); 13C NMR
(76 MHz, Chloroform-d) δ 191.29, 158.40, 135.50, 130.97, 129.70,
126.33, 117.42, 34.98. MS (EI, 70 eV): m/z = 202 [M+]; Anal. calcd for
C13H14O2: C, 77.20; H, 6.98. Found: C, 77.16; H, 7.08.
4.18
|
2,6-diallyl-4-methylphenol (39)
4.23
|
2,6-diallyl-4-nitrophenol (45)
Yellow oil, 1H NMR (301 MHz, Chloroform-d) δ 6.73 (s, 2H), 5.92 (ddt,
J = 16.7, 10.2, 6.4 Hz, 2H), 5.11–5.05 (dq, J = 8.2, 1.6 Hz, 1H), 5.03
(m, 2H), 4.92 (s, 1H), 3.28 (d, J = 6.4 Hz, 4H), 2.16 (s, 3H); 13C NMR
(76 MHz, Chloroform-d) δ 150.38, 136.81, 129.83, 129.27, 125.52,
116.31, 35.38, 20.57. MS (EI, 70 eV): m/z = 189 [M+]; Anal. calcd for
Yellow oil, 1H NMR (301 MHz, Chloroform-d) δ 7.68 (s, 2H), 7.09 (s,
1H), 5.93 (m, 2H), 5.89–5.69 (m, 4H), 3.49 (d, J = 6.4 Hz, 4H).13
C
NMR (76 MHz, Chloroform-d) δ 161.06, 151.35, 136.65, 126.86,
117.98, 115.91, 33.47. MS (EI, 70 eV): m/z = 219 [M+]; Anal. calcd for
C12H13NO3: C, 65.74; H, 5.98; N, 6.39. Found: C, 65.80; H,
C
13H16O: C, 82.94; H, 8.57. Found: C, 83.05; H, 8.74.
6.00; N, 6.40.
4.19
|
2,6-diallyl-4-methoxyphenol (40)
4.24
|
2,6-diallyl-4-(hydroxymethyl)phenol (46)
Yellow oil, 1H NMR (301 MHz, Chloroform-d)
δ
6.51 (s, 2H),
Yellowishoil,1H NMR (301 MHz, Chloroform-d) δ 6.93 (s, 2H), 6.74 (s,
1H), 5.93 (m, 2H), 5.15–4.95 (m, 4H), 4.48 (s, 2H), 3.33 (d, J = 6.1 Hz,
4H), 2.00 (s, 1H)13C NMR (76 MHz, Chloroform-d) δ 150.88, 136.74,
129.06, 125.58, 116.29, 111.52, 68.85, 35.37. MS (EI, 70 eV): m/
z = 204 [M+]; Anal. calcd for C13H16O2: C, 76.44; H, 7.90. Found: C,
77.01; H, 8.08.
6.03–5.85 (m, 2H), 5.10 (m, 2H), 5.07–5.03 (m, 2H), 4.70 (s, 1H), 3.68
(s, 3H), 3.31 (d, J = 6.4 Hz, 4H); 13C NMR (76 MHz, Chloroform-d) δ
153.39, 146.43, 136.41, 126.84, 116.47, 113.81, 55.65, 35.52. MS
(EI, 70 eV): m/z = 204 [M+]; Anal. calcd for C13H16O2: C, 76.44; H,
7.90. Found: C, 77.01; H, 7.96.
4.20
|
2,6-diallyl-4-(hexyloxy)phenol (42)
4.25
|
2,6-diallyl-4-aminophenol (47)
Yellow oil, 1H NMR (301 MHz, Chloroform-d) δ 6.50 (s, 2H), 5.91 (m,
2H), 5.08 (dq, J = 4.5, 1.5 Hz, 1H), 5.04 (t, J = 1.5 Hz, 2H), 4.70 (s, 1H),
3.80 (t, J = 6.6 Hz, 2H), 3.29 (d, J = 6.4 Hz, 4H), 1.74–1.60 (m, 2H),
1.43–1.30 (m, 2H), 1.24 (m, 4H), 0.82 (t, J = 6.8 Hz, 3H); 13C NMR
(76 MHz, Chloroform-d) δ 153.29, 147.86, 136.25, 126.41, 116.68,
113.28, 68.59, 35.33, 31.65, 29.40, 25.77, 22.65, 14.09. MS (EI,
Yellow crystals (mp: 77–78ꢀC),1H NMR (301 MHz, Chloroform-d) δ
6.43 (s, 2H), 6.02 (ddt, J = 16.0, 10.9, 6.4 Hz, 2H), 5.18 (dq, J = 6.5,
1.7 Hz, 2H), 5.14 (m, 2H), 3.36 (b, 7H); 13C NMR (76 MHz,
Chloroform-d) δ 145.34, 139.65, 136.68, 126.98, 116.21, 115.75,
35.34. MS (EI, 70 eV): m/z = 189 [M+]; Anal. calcd for C12H15NO: C,
76.16; H, 7.99; N, 7.40. Found: C, 76.16; H, 7.99; N, 7.40.