Molecules 2016, 21, 643
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by flash chromatography (CH Cl /CH OH 9.5:0.5) to give a semisolid compound, Yield = 51%, HCl;
2
2
3
˝
1
mp: 264–268 C. H-NMR (400 MHz, CDCl ) δ 2.33 (s, 3H, NCH ), 2.55 (s, 3H, COCH ), 3.56 (s, 2H,
3 3
3
NCH ), 3.59 (s, 2H, NCH ), 3.90–3.94 (m, 4H, OCH CH O), 6.48 (d, J = 2.2 Hz, 1H, Ch-Ar), 6.51
2
2
2
2
(
(
2
dd, J = 8.0 and 2.2 Hz, 1H, Ch-Ar), 7.00 (d, 2H, J = 8.40 Hz, Bf-Ar), 7.26–7.46 (m, 5H, Bn-Ar), 7.49
d, 2H, J = 8.60 Hz, Bf-Ar), 7.63 (d, 1H, J = 8.0 Hz, Ch-Ar), 7.75 (d, 2H, J = 8.60 Hz, Bf-Ar), 7.85 (d,
H, J = 8.60 Hz, Bf-Ar). 13C-NMR (101 MHz, CDCl3):
δ
26.64, 61.055, 61.62, 64.34, 64.66, 103.87, 106.98,
1
1
13.44, 126.90, 128.12, 128.52, 128.74, 128.86, 129.77, 130.41, 132.41, 136.91, 138.22, 143.69, 162.59, 165.11,
66.65, 197.56, 202.61. (ESI ) 510 m/z: [M + H] .
+
+
E-1-{4-[2-(4-4-Benzylmethylaminomethylbenzoylphenoxy)ethoxy]-2-hydroxyphenyl}-3-(3,4,5-trimethoxy-
phenyl)prop-2-en-1-one ( ). Reaction of Bp (1.0 mmol, 0.33 g) and chalcone (Ch) 11 (1.1 mmol, 0.48 g)
gave a crude product that was purified by flash chromatography (CH Cl /CH OH 9.25:0.75) to give
4
8
2
2
3
˝
1
a semisolid compound. Yield = 65%, HCl; mp: 220–222 C. H-NMR (400 MHz, CDCl )
δ
2.30 (s, 3H,
3
NCH ), 3.57 (s, 2H, NCH ), 3.59 (s, 2H, NCH ), 3.91 (s, 3H, OCH ), 3.94 (s, 6H, OCH ), 4.20–4.34
3
2
2
3
3
(
(
m, 4H, OCH CH O), 6.50 (d, J = 2.2 Hz, 1H, Ch-Ar), 6.54 (dd, J = 8.0 and 2.2 Hz, 1H, Ch-Ar), 6.87
2 2
s, 2H, Ch-Ar), 7.00 (d, 2H, J = 8.60 Hz, Bp-Ar), 7.16–7.36 (m, 5H, Bn-Ar), 7.26 (d, 1H, J = 15.60 Hz
,
Ch-
Ch-
β
CH=CH), 7.72 (d, 2H, J = 8.60 Hz, Ch-Ar), 7.78 (d, 1H, J = 8.60 Hz, Bp-Ar), 7.85 (d, 1H, J = 15.60 Hz
,
13
α
CH=CH), 7.88 (d, 2H, J = 8.60 Hz, Bp-Ar); C-NMR (101 MHz, CDCl3):
δ
56.11, 60.85, 64.34,
6
4.66, 103.86, 106.93, 113.45, 118.74, 126.96, 128.17, 128.56, 128.71, 128.80, 129.70, 130.46, 132.45,
+
+
1
36.92, 138.24, 143.68, 145.32, 153.01, 153.22, 162.5, 165.11, 166.62, 197.58, 192.41. (ESI ) m/z: 687 [M + H] .
E-1-{4-[2-(4-4-Benzylmethylaminomethylbenzoylphenoxy)ethoxy]-2-hydroxyphenyl}-3-(naphthalen-1-yl)-
prop-2-en-1-one ( ). Reaction of Bp (1.0 mmol, 0.33 g) and Ch 12 (1.1 mmol, 0.44 g) gave a crude
product that was purified by flash chromatography (CH Cl /CH OH 9.25:0.75) to give a semisolid
5
8
2
2
3
˝
1
compound. Yield = 51%, HCl: mp: 197–99 C. H-NMR (400 MHz, CDCl )
δ 2.32 (s, 3H, NCH ), 3.59
3
3
(
s, 2H, NCH ), 3.62 (s, 2H, NCH ), 4.30–4.40 (m, 4H, OCH CH O), 6.55 (d, J = 2.2 Hz, 1H, Ch-Ar), 6.58
2 2 2 2
(
dd, J = 8.0 and 2.2 Hz, 1H, Ch-Ar), 7.02 (d, 2H, J = 8.60 Hz, Bf-Ar), 7.20–7.61 (m, 10H, Ar), 7.75 (d, 1H,
-CH=CH), 7.79–7.97(m, 8H, Ar), 8.03 (d, 1H, J = 8.0 Hz, Ch-Ar), 8.75 (d, 1H, J = 15.60 Hz
CH=CH); 13C NMR (101 MHz, CDCl3):
61.05, 61.62, 64.34, 64.66, 103.88, 106.96, 113.44, 121.33,
22.85, 126.14, 126.99, 128.19, 128.51, 128.76, 128.83, 129.72, 130.43, 132.48, 132.47, 133.54, 135.54, 136.94,
J = 16.4 Hz,
α
β
,
δ
1
1
+
+
38.23, 143.63, 162.59, 165.11, 166.65, 197.50, 192.81. (ESI ) m/z: 648 [M + H] .
-{2-[4-(4-Benzylmethylaminomethylbenzoyl)phenoxy]ethoxy}-2-(3,4,5-trimethoxyphenyl)chroman-4-one (
Reaction of Bp (1.0 mmol, 0.33 g) and flavone (Fl) 13 (1.1 mmol, 0.48 g) gave a crude product
that was purified by flash chromatography (CH Cl /CH OH 9.5:0.5) to give a semisolid compound.
7
6).
8
2
2
3
˝
1
Yield = 59%, HCl: mp: 182–94 C. H-NMR (400 MHz, CDCl )
δ 2.32 (s, 3H, NCH ), 2.87 (dd, 1H,
3
3
J = 16.5 and 2.8 Hz, H3a-Fl), 3.06 (dd, 1H, J = 16.5 and 13.1 Hz, H3b-Fl) 3.70 (s, 2H, NCH ), 3.74 (s, 2H,
2
NCH ), 3.87 (s, 3H, OCH ),3.90 (s, 6H, OCH ), 4.40–4.46 (m, 4H, OCH CH O), 5.37 (dd, 1H, J = 13.1
2
3
3
2
2
and 2.8 Hz, H2-Fl), 6.57 (d, J = 2.2 Hz, 1H, Fl-Ar), 6.70 (dd, J = 8.0 and 2.2 Hz, 1H, Fl-Ar), 6.75 (s, 2H,
Fl-Ar), 7.00 (d, 2H, J = 8.60 Hz, Bf-Ar), 7.26–7.36 (m, 5H, Bn-Ar), 7.78 (d, 1H, J = 8.60 Hz, Bf-Ar), 7.81
(
5
1
d, 2H, J = 8.60 Hz,Bf-Ar), 7.86 (d, 2H, J = 8.60 Hz,Bf-Ar); 13C-NMR (101 MHz, CDCl3):
δ
42.45, 56.10,
9.21, 61.05, 61.62, 64.34, 64.66, 83.44, 101.74, 103.86, 106.93, 113.46, 126.98, 128.12, 128.54, 128.76, 128.82,
29.78, 130.45, 132.43, 134.91, 136.92, 138.22, 143.67, 153.21, 138.74, 163.25, 165.11, 166.65, 197.51, 190.21.
+
+
MS (ESI ) m/z: 689 [M + H] .
-{2-[4-(4-(Benzylmethylaminomethylbenzoyl)phenoxy]ethoxy}-2-(naphthalen-1-yl)chroman-4-one
Reaction of Bf (1.0 mmol, 0.33 g) and Fl 13 (1.1 mmol, 0.44 g) gave a crude product that was purified
by flash chromatography (CH Cl /CH OH 9.5:0.5) to give a semisolid compound. Yield = 45%, HCl:
7
(7).
8
2
2
3
˝
1
mp: 172–95 C. H-NMR (400 MHz, CDCl )
δ 2.22 (s, 3H, NCH ), 3.03 (dd, 1H, J = 16.5 and 2.8 Hz,
3
3
H3a-Fl), 3.26 (dd, 1H, J = 16.5 and 13.1 Hz, H3b-Fl) 3.54 (s, 2H, NCH ), 3.61 (s, 2H, NCH ), 4.36–4.48
2
2
(
(
m, 4H, OCH CH O), 6.21 (dd, 1H, J = 13.1 and 2.8 Hz, H2-Fl), ), 6.57 (d, J = 2.2 Hz, 1H, Fl-Ar), 6.58
2 2
dd, J = 8.0 and 2.2 Hz, 1H, Fl-Ar), 7.02 (d, 2H, J = 8.60 Hz, Bf-Ar), 7.20–7.61 (m, 10H, Ar), 7.79–7.97(m,