35.06, 34.82, 31.34, 31.01; ESI-MS m/z calcd for C22H26O2N [M + NH4]+ 336.2, found 336.6.
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4.1.7.17. 4-(4,4-Diphenylbutyl)benzene-1,2-diol (WB5). Yellow oil, yield 57%, Rf = 0.38 (DCM/MeOH = 30:1); H
NMR (400 MHz, DMSO-d6) δ 8.67 (s, 1H, OH), 8.56 (s, 1H, OH), 7.31–7.22 (m, 8H, Ar-H), 7.14 (dd, J = 6.0, 3.1 Hz,
2H, Ar-H), 6.58 (d, J = 7.9 Hz, 1H, H-5), 6.49 (d, J = 2.0 Hz, 1H, H-2), 6.35 (dd, J = 8.0, 2.0 Hz, 1H, H-6), 3.93 (t, J
= 7.9 Hz, 1H, Ph-CH-Ph), 2.41 (t, J = 7.6 Hz, 2H, Ph-CH2), 1.99 (q, J = 7.9 Hz, 2H, CH2CH2CH2CHPh2), 1.39 (td, J
= 7.6, 7.1, 3.7 Hz, 2H, CH2CH2CH2CHPh2); 13C NMR (100 MHz, CDCl3) δ 143.30, 141.72, 141.23, 141.13, 138.63,
135.90, 128.84 (2C), 128.71 (2C), 128.68, 127.02 (2C), 126.99 (2C), 120.87, 115.51, 115.26, 35.45, 35.08, 31.18,
30.96; ESI-MS m/z calcd for C24H22O4F3 [M + CF3COO] – 431.2, found 431.6.
4.1.7.18. 4-(4-(Naphthalen-1-yl)butyl)benzene-1,2-diol (WB6). White solid, yield 34%, mp 136–138 °C, Rf = 0.59
1
(DCM/MeOH = 10:1); H NMR (400 MHz, DMSO-d6) δ 8.67 (s, 1H, OH), 8.57 (s, 1H, OH), 8.03 (dd, J = 7.8, 1.6
Hz, 1H, H-8ʹ), 7.93–7.85 (m, 1H, H-5ʹ), 7.75 (d, J = 8.1 Hz, 1H, H-4ʹ), 7.51 (pd, 2H, H-6ʹ and H-3ʹ), 7.40 (dd, J = 8.1,
7.0 Hz, 1H, H-7ʹ), 7.33 (dd, J = 7.0, 1.3 Hz, 1H, H-2ʹ), 6.61 (d, J = 7.9 Hz, 1H, H-5), 6.56 (d, J = 2.1 Hz, 1H, H-2),
6.42 (dd, J = 8.0, 2.1 Hz, 1H, H-6), 3.04 (t, J = 7.2 Hz, 2H, Arʹ-CH2), 2.45 (t, J = 7.1 Hz, 2H, Ph-CH2), 1.69–1.58 (m,
4H, CH2CH2CH2CH2); 13C NMR (150 MHz, DMSO-d6) δ 145.41, 143.53, 138.91, 133.91, 133.40, 131.81, 129.01,
126.72, 126.35, 126.31, 126.03, 125.94, 124.22, 119.31, 116.15, 115.84, 34.80, 32.56, 31.67, 30.55; ESI-MS m/z
calcd for C22H20O4F3 [M + CF3COO] – 405.1, found 405.6.
4.1.7.19. 4-(4-(6-Hydroxynaphthalen-2-yl)butyl)benzene-1,2-diol (WB7). White solid, yield 51%, mp 147–149 °C, Rf
= 0.55 (DCM/MeOH = 10:1); 1H NMR (400 MHz, DMSO-d6) δ 9.58 (s, 1H, Arʹ-OH), 8.67 (s, 1H, Ph-OH ), 8.57 (s,
1H, Ph-OH), 7.66 (d, J = 8.7 Hz, 1H, H-8ʹ), 7.58 (d, J = 8.4 Hz, 1H, H-4ʹ), 7.51 (d, J = 1.6 Hz, 1H, H-5ʹ), 7.23 (dd, J
= 8.4, 1.7 Hz, 1H, H-3ʹ), 7.06 (d, J = 2.4 Hz, 1H, H-7ʹ), 7.03 (dd, 1H, H-2ʹ), 6.59 (d, J = 7.9 Hz, 1H, H-5 ), 6.53 (d, J
= 2.1 Hz, 1H, H-2), 6.39 (dd, J = 8.0, 2.1 Hz, 1H, H-6), 2.68 (t, J = 7.4 Hz, 2H, Arʹ-CH2), 2.42 (t, J = 7.4 Hz, 2H,
Ph-CH2), 1.57 (dq, J = 31.9, 7.5 Hz, 4H, CH2CH2CH2CH2); 13C NMR (150 MHz, DMSO-d6) δ 155.11, 145.39,
143.52, 136.82, 133.46, 133.42, 129.17, 128.28, 127.99, 126.39, 126.33, 119.28, 118.94, 116.11, 115.84, 108.95,
35.39, 34.85, 31.36, 31.03; ESI-MS m/z calcd for C21H21O4 [M + HCOO] – 353.1, found 353.3.
4.1.7.20. 4-(4-(1-Methyl-1H-indol-3-yl)butyl)benzene-1,2-diol (WB8). Yellow oil, yield 44%, Rf = 0.24 (DCM/MeOH
1
= 30:1); H NMR (400 MHz, DMSO-d6) δ 8.67 (s, 1H, OH), 8.57 (s, 1H, OH), 7.48 (dt, J = 7.8, 1.0 Hz, 1H, H-6ʹ),
7.35 (dd, J = 8.2, 0.9 Hz, 1H, H-7ʹ), 7.11 (ddd, J = 8.2, 7.0, 1.2 Hz, 1H, I H-4ʹ), 7.04 (s, 1H, H-2ʹ), 6.98 (ddd, J = 7.9,
7.0, 1.0 Hz, 1H, H-5ʹ), 6.60 (d, J = 7.9 Hz, 1H, H-5), 6.54 (d, J = 2.1 Hz, 1H, H-2), 6.40 (dd, J = 8.0, 2.1 Hz, 1H,
H-6), 3.71 (s, 3H, CH3), 2.66 (d, J = 7.3 Hz, 2H, Ph-CH2 ), 2.43 (t, J = 7.2 Hz, 2H, Arʹ-CH2), 1.59 (dq, J = 21.8, 7.9
Hz, 4H, CH2CH2CH2CH2); 13C NMR (150 MHz, CDCl3) δ 143.32, 141.32, 137.04, 135.97, 127.96, 126.12, 121.38,
120.87, 120.85, 119.11, 118.45, 115.50, 115.20, 109.13, 35.09, 32.56, 31.40, 29.88, 24.94; ESI-MS m/z calcd for
C19H22NO2 [M + H]+ 296.2, found 296.3.
4.1.7.21. 4-(4-(1-Isopentyl-1H-indol-3-yl)butyl)benzene-1,2-diol (WB9). Yellow oil, yield 44%, Rf = 0.13
(DCM/MeOH = 10:1); 1H NMR (400 MHz, DMSO-d6) δ 8.65 (s, 1H, OH), 8.56 (s, 1H, OH), 7.48 (dt, J = 7.9, 1.0 Hz,
1H, H-6ʹ), 7.37 (dt, J = 8.2, 0.9 Hz, 1H, H-7ʹ), 7.13–7.06 (m, 2H, H-4ʹ and H-2ʹ), 6.96 (ddd, J = 7.9, 7.0, 1.0 Hz, 1H,
H-5ʹ), 6.59 (d, J = 7.9 Hz, 1H, H-5), 6.54 (d, J = 2.1 Hz, 1H, H-2), 6.40 (dd, J = 8.0, 2.1 Hz, 1H, H-6), 4.10 (t, J = 7.3
Hz, 2H, NCH2CH2), 2.67 (t, J = 7.2 Hz, 2H, Ph-CH2), 2.43 (t, J = 7.3 Hz, 2H, Arʹ-CH2), 1.70–1.58 (m, 4H,
CH2CH2CH2CH2), 1.58–1.38 (m, 2H, NCH2CH2), 1.09 (t, J = 7.0 Hz, 1H, CH(CH3)2), 0.90 (d, J = 6.6 Hz, 6H,
2×CH3); 13C NMR (150 MHz, CDCl3) δ 143.26, 141.25, 136.27, 136.04, 128.01, 124.90, 121.20, 120.87, 119.32,
119.18, 118.34, 115.51, 115.21, 109.26, 44.34, 39.12, 35.06, 31.39, 29.81, 25.79, 25.00, 22.49 (2C); ESI-MS m/z
calcd for C23H30NO2 [M + H]+ 352.2, found 352.9.
4.1.7.22. 4-(4-(3,4,5,6-Tetrahydroanthracen-9-yl)butyl)benzene-1,2-diol (WB10). White solid, yield 65%, mp 158–
160 °C, Rf = 0.25 (DCM/MeOH = 30:1); 1H NMR (400 MHz, DMSO-d6) δ 8.68 (s, 1H, OH), 8.59 (s, 1H, OH), 7.94–
7.89 (m, 1H, H-6ʹ), 7.72 (dd, J = 7.5, 2.0 Hz, 1H, H-2ʹ), 7.45 (s, 1H, H-10ʹ), 7.37 (td, J = 7.2, 1.6 Hz, 2H, H-3ʹ and
H-9ʹ), 6.62 (d, J = 7.9 Hz, 1H, H-5), 6.54 (d, J = 2.1 Hz, 1H, H-2), 6.45 (dd, J = 8.0, 2.1 Hz, 1H, H-6), 3.02 – 2.95 (m,
2H, Arʹ-CH2), 2.90 (t, J = 6.3 Hz, 2H, CH2), 2.85 (t, J = 6.5 Hz, 2H, CH2), 2.48 (d, J = 7.4 Hz, 2H, Ph-CH2), 1.81 (q,
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