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K. Uwai et al. / Bioorg. Med. Chem. 16 (2008) 7795–7803
tone-d6) d: 167.4, 148.7, 146.3, 145.5, 127.7, 122.4, 116.4, 115.8,
115.2, 64.6, 34.5, 29.7, 29.6, 26.7, 23.2, 14.3. MS m/z: 278 (M+),
261, 250, 235, 221, 207, 193, 180 (100%), 163, 117, 77. High-reso-
lution MS calcd for C16H22O4 (M+): 278.1519. Found: 278.1530.
Anal. calcd for C16H22O4: 69.04% C, 7.97% H. Found: 69.12% C,
8.26% H. All spectral data agreed with previously reported data.24
146.8, 146.8, 127.7, 122.9, 116.5, 115.2, 115.1, 65.6, 33.1, 30.7,
30.7, 30.6, 30.5, 30.4, 29.8, 27.1, 23.7, 14.4. MS m/z: 334 (M+),
292, 278, 236, 193, 180 (100%), 163, 136. High-resolution MS calcd
for C20H30O4 (M+): 334.2145. Found: 334.2137. Anal. calcd for
C20H30O4: 71.82% C, 9.04% H. Found: 71.63% C, 9.20% H.
4.8.12. Dodecyl 1-(30,40-dihydroxyphenyl)propenate (n-dodecyl
caffeate) (12)
4.8.8. Octyl 1-(30,40-dihydroxyphenyl)propenate (n-octyl
caffeate) (8)
Yield: 44%. Mp: 105–106 °C (recrystallized from Et2O, colorless
needles). FT-IR vmax (KBr): 3482, 3313, 2956, 2921, 2850, 1685,
1606, 1532. 1H NMR (270 MHz, CDCl3) d: 7.57 (1H, d, J = 16.0 Hz),
7.08 (1H, d, J = 2.0 Hz), 7.02 (1H, dd, J = 2.0, 8.2 Hz), 6.87 (1H, d,
J = 8.2 Hz), 6.27 (1H, d, J = 16.0 Hz), 4.18 (2H, t, J = 6.7 Hz), 1.69
(2H, quint, J = 6.7 Hz), 1.45–1.18 (18H, m), 0.88 (3H, t, J = 6.9 Hz).
13C NMR (67.8 MHz, DMSO-d6) d: 166.9, 148.7, 146.0, 145.3,
125.9, 121.6, 116.0, 115.0, 114.3, 64.0, 31.8, 30.9, 29.5, 29.5, 29.4,
29.2, 29.2, 28.7, 25.9, 22.5, 14.2. MS m/z: 348 (M+), 320, 235, 221,
193, 180 (100%), 163, 136. High-resolution MS calcd for C21H32O4
(M+): 348.2302. Found: 348.2306. Anal. calcd for C21H32O4:
72.38% C, 9.26% H. Found: 72.43% C, 9.52% H. All spectral data
agreed with previously reported data.22
Yield: 66%. Mp: 110–111 °C (recrystallized from Et2O, colorless
needles). FT-IR vmax (KBr): 3488, 3319, 2921, 2856, 1679, 1606,
1532. 1H NMR (270 MHz, acetone-d6) d: 8.41 (1H, s), 8.13 (1H, s),
7.54 (1H, d, J = 16.0 Hz), 7.15 (1H, d, J = 2.0 Hz), 7.03 (1H, dd,
J = 2.0, 8.1 Hz), 6.86 (1H, d, J = 8.1 Hz), 6.28 (1H, d, J = 16.0 Hz),
4.13 (2H, t, J = 6.7 Hz), 1.66 (2H, quint, J = 6.7 Hz), 1.45–1.14
(10H, m), 0.86 (3H, t, J = 6.9 Hz). 13C NMR (67.8 MHz acetone-d6)
d: 167.4, 148.6, 146.2, 145.5, 127.6, 122.42, 116.3, 115.7, 115.1,
64.7, 32.5, 29.9, 29.9, 29.5, 26.6, 23.2, 14.3. MS m/z: 292 (M+),
193, 180 (100%), 163, 117. High-resolution MS calcd for C17H24O4
(M+): 292.1675. Found: 292.1683. Anal. calcd for C17H24O4: 69.8%
C, 8.27% H. Found: 69.7% C, 8.45% H. All spectral data agreed with
previously reported data.21,25
4.8.13. Tetradecyl 1-(30,40-dihydroxyphenyl)propenate (n-
tetradecyl caffeate) (13)
4.8.9. Nonyl 1-(30,40-dihydroxy phenyl)propenate (n-nonyl
caffeate) (9)
Yield: 35%. Mp: 108–109 °C (recrystallized from CHCl3–toluene,
colorless needles). FT-IR vmax(KBr): 3480, 3310, 2956, 2918, 2849,
1686, 1604, 1532. 1H NMR (400 MHz, DMSO-d6) d: 9.41 (2H, br
s), 7.45 (1H, d, J = 16.0 Hz), 7.02 (1H, d, J = 2.0 Hz), 6.96 (1H, dd,
J = 2.0, 8.3 Hz), 6.74 (1H, d, J = 8.3 Hz), 6.22 (1H, d, J = 16.0 Hz),
4.07 (2H, t, J = 6.8 Hz), 1.59 (2H, quint, J = 6.8 Hz), 1.37–1.13
(22H, m), 0.82 (3H, t, J = 6.3 Hz). 13C NMR (100 MHz, DMSO-d6) d:
166.6, 148.5, 145.7, 145.1, 125.6, 121.3, 115.8, 114.9, 114.1, 63.8,
31.4, 29.3–29.2 (C ꢁ 4), 29.1, 29.1, 28.9, 28.8, 28.4, 25.6, 22.2,
14.0. MS m/z: 376 (M+), 348, 334, 269, 193, 180 (100%), 163, 136.
High-resolution MS calcd for C23H36O4 (M+): 376.2615. Found:
376.2614. Anal. calcd for C23H36O4: 70.56% C, 8.55% H. Found:
73.51% C, 9.93% H. All spectral data agreed with previously re-
ported data.22
Yield: 68%. Mp: 105–106 °C (recrystallized from n-hexane–Et2O,
colorless needles). FT-IR vmax (KBr): 3489, 3331, 2960, 2923, 2848,
1686, 1604, 1536. 1H NMR (270 MHz, acetone-d6) d: 8.42 (1H, s),
8.13 (1H, s), 7.53 (1H, d, J = 16.0 Hz), 7.15 (1H, d, J = 2.0 Hz), 7.04
(1H, dd, J = 2.0, 8.2 Hz), 6.86 (1H, d, J = 8.2 Hz), 6.27 (1H, d,
J = 16.0 Hz), 4.13 (2H, t, J = 6.6Hz), 1.67 (2H, quint, J = 6.6 Hz),
1.46–1.19 (12H, m), 0.87 (3H, t, J = 6.9 Hz). 13C NMR (67.8 MHz ace-
tone-d6) d: 167.4, 148.7, 146.3, 145.5, 127.7, 122.4, 116.4, 115.8,
115.2, 64.6, 32.6, 30.2, 30.0, 30.0, 26.7, 23.3, 14.3. MS m/z: 306
(M+), 278, 249, 235, 221, 207, 193, 180 (100%), 163, 136, 117.
High-resolution MS calcd for C18H26O4 (M+): 306.1832. Found:
306.1839. Anal. calcd for C18H26O4: 70.56% C, 8.55% H. Found:
70.53% C, 8.67% H. All spectral data agreed with previously re-
ported data.26
4.8.14. Hexadecyl 1-(30,40-dihydroxyphenyl)propenate (n-
hexadecyl caffeate) (14)
4.8.10. Decanyl 1-(30,40-dihydroxyphenyl)propenate (n-decanyl
caffeate) (10)
Yield: 47%. Mp: 110–111 °C (recrystallized from Et2O, colorless
needles). FT-IR vmax (KBr): 3480, 3308, 2956, 2916, 2849, 1690,
1607, 1532. 1H NMR (400 MHz, CD3OD) d: 7.5 21Y, d, J = 16.1 Hz,
7.0 31Y, d, J = 2.0 Yz), 6.93 (1H, dd, J = 2.0, 7.8Hz), 6.77 (1H, d,
J = 7.8 Hz), 6.25 (1H, d, J = 16.1 Hz), 4.16 (2H, t, J = 6.3 Hz), 1.69
(2H, quint), 1.44–1.15 (26H, m), 0.89 (3H, t, J = 7.3 Hz). 13C NMR
(100 MHz, CD3OD) d: 169.4, 149.6, 146.8, 146.8, 127.7, 122.9,
116.5, 115.2, 115.1, 65.6, 33.1, 30.8–30.7 (Cꢁ6), 30.6, 30.6, 30.5,
30.3, 29.8, 27.1, 23.7, 14.4. MS m/z: 404 (M+), 376, 291, 239, 180
(100%), 163, 136. High-resolution MS calcd for C25H40O4 (M+):
404.2928. Found: 404.2906. Anal. calcd for C25H40O4: 74.22% C,
9.97% H. Found: 74.32% C, 10.42% H. All spectral data agreed with
previously reported data.22,23
Yield: 89%. Mp: 111–112 °C (recrystallized from n-hexane–
Et2O, colorless needles). FT-IR vmax(KBr): 3485, 3313, 1684, 1606,
1532, 1474, 1317, 1246, 1179, 1110, 975, 861, 1H NMR
(270 MHz, CDCl3) d: 7.59 (1H, d, J = 16.0 Hz), 7.08 (1H, d,
J = 1.8 Hz), 7.02 (1H, dd, J = 1.8, 8.1 Hz), 6.87 (1H, d, J = 8.1 Hz),
6.27 (1H, d, J = 16.0 Hz), 5.39 (1H, S), 5.25 (1H, S), 4.18 (2H, t,
J = 6.8 Hz), 1.69 (2H, quint, J = 6.8 Hz), 1.46–1.14 (14H, m), 0.88
(3H, t, J = 6.6 Hz). 13C NMR (67.8 MHz, CDCl3) d: 168.0, 146.2,
144.8, 143.7, 127.6, 122.4, 115.8, 115.5, 114.5, 77.2, 64.9, 31.9,
29.5, 29.3, 29.3, 28.7, 26.0, 22.7, 14.1. MS m/z: 320 (M+), 264,
221, 180 (100%), 163, 136, 117. High-resolution MS calcd for
C
C
19H28O4 (M+): 320.1988. Found: 320.1979. Anal. calcd for
19H28O4: 71.2% C, 8.81% H. Found: 71.2% C, 9.04% H. All spectral
data agreed with previously reported data.22,27
4.8.15. Octadecyl 1-(30,40-dihydroxyphenyl)propenate (n-
octadecyl caffeate) (15)
4.8.11. Undecyl 1-(30,40-dihydroxy phenyl)propenate (n-undecyl
caffeate) (11)
Yield: 38%. Mp: 110–112 °C (recrystallized from CHCl3, colorless
needles). FT-IR vmax (KBr): 3481, 3312, 2926, 2920, 2851, 1684,
1607, 1532. 1H NMR (400 MHz, DMSO-d6) d: 9.57 (1H, s), 9.11
(1H, s), 7.45 (1H, d, J = 15.6 Hz), 7.03 (1H, d, J = 2.0 Hz), 6.98 (1H,
dd, J = 2.0, 8.3 Hz), 6.74 (1H, d, J = 8.3 Hz), 6.24 (1H, d,
J = 15.6 Hz), 4.08 (2H, t, J = Hz), 1.60 (2H, quint), 1.34–1.10 (30H,
m), 0.84 (3H, t, J = 6.3 Hz). 13C NMR (100 MHz, DMSO-d6) d:
166.5, 148.3, 145.5, 144.9, 125.5, 121.5, 121.3, 115.7, 114.8,
114.0, 63.6, 31.2, 28.9–28.8 (Cꢁ10), 28.6, 28.6, 28.2, 25.4, 22.0,
Yield: 23%. Mp: 109–110.5 °C (recrystallized from Et2O, color-
less needles). FT-IR vmax (KBr): 3488, 3333, 2959, 2918, 2850,
1687, 1604, 1536. 1H NMR (400 MHz, CD3OD) d: 7.52 (1H, d,
J = 16.0 Hz), 7.03 (1H, d, J = 2.0 Hz), 6.93 (1H, dd, J = 2.0, 7.8 Hz),
6.76 (1H, d, J = 7.8 Hz), 6.24 (1H, d, J = 16.0 Hz), 4.15 (2H, t,
J = 6.8 Hz), 1.68 (2H, quint, J = 6.8 Hz), 1.45–1.18 (16H, m), 0.88
(3H, t, J = 6.8 Hz). 13C NMR (100 MHz, CD3OD) d: 169.4, 149.5,