Medicinal Chemistry Research
(
2E,5E)-2,5-Bis(3-ethoxy-4-(prop-2-yn-1-yloxy)benzylidene)
= CH-, C-2, C-2′), 122.5 (Ar-C, C-9, C-9′), 114.4 (Ar-C, C-
8, C-8′), 112.2 (Ar-C, C-5, C-5′), 78.3 (-C ≡ CH-), 76.3
cyclopentanone (4d)
(
-C ≡ CH-), 64.7 (OCH -CH ), 56.8 (Ar-OCH ), 14.9
2
3
2
+
Yellow coloured crystal; yield 81%; mp: 177–179 °C; IR
(OCH -CH ); LC-MS: Calcd for C H O [M + H] ,
2 3 27 27 5
−
1 1
(
(
KBr) νmax 3253, 2119, 1672, 1581, 1505 cm ; H NMR
431.5, found: 431.1
CDCl , 400 MHz,): δ = 7.53 (2H, s, Ar-CH = C-, H-3, H-
3
3
7
′), 7.23 (2H, dd, J = 8.4 Hz and 1.6 Hz, Ar-H, H-9, H-9′),
.15 (2H, d, J = 1.6 Hz, Ar-H), 7.11 (2H, d, J = 8.4 Hz, Ar-
(1E,4E)-1,5-Bis(3-methoxy-4-(prop-2-yn-1-yloxy)phenyl)
penta-1,4-dien-3-one (4g)
H), 4.83 (4H, d, J = 2.4 Hz, Ar-OCH ), 4.15 (4H, q, J =
2
7
.2 Hz, -OCH CH ), 3.10 (4H, s, -CH ), 2.53 (2H, d, J =
Yellow coloured crystal; yield 82%; mp: 155–157 °C; IR
(KBr) νmax 3253, 2109, 1660, 1571, 1495 cm ; H NMR
2
3
2
1
3
−1 1
2
.4 Hz, -C ≡ CH), 1.49 (6H, t, J = 7.2 Hz, -OCH -CH );
C
2
3
NMR (CDCl , 100 MHz,): δ = 196.1 (C = O, C-1), 148.9
(CDCl , 400 MHz,): δ = 7.71 (2H, d, J = 16 Hz, Ar-CH =
3
3
(
=
Ar-C, C-7, C-7′), 148.3 (Ar-C, C-6, C-6′), 135.8 (Ar-CH
C-, C-3, C-3′), 133.6 (Ar-CH = C-, C-2, C-2′), 130.2 (Ar-
C, C-4, C-4′), 124.0 (Ar-C, C-9, C-9′), 115.6 (Ar-C, C-8, C-
′), 114.4 (Ar-C, C-5, C-5′), 78.3 (-C ≡ CH-), 76.1 (-C ≡
CH-), 64.7 (OCH -CH ), 56.7 (Ar-OCH ), 26.5 (-CH ),
C-, H-3, H-3′), 7.22 (2H, d, J = 8.4 Hz, Ar-H, H-9, H-9′),
7.17 (2H, s, Ar-H, H-5, H-5′), 7.07 (2H, d, J = 8 Hz, Ar-H,
H-8, H-8′), 6.98 (2H, d, J = 16 Hz, Ar-CH = CH-, H-2, H-
8
2′), 4.84 (4H, d, J = 2.4 Hz, Ar-OCH ), 3.96 (6H, s,
2
1
3
-OCH ), 2.57 (2H, t, J = 2.4 Hz, -C ≡ CH); C NMR
2
3
2
2
+
3
1
4.8 (OCH -CH ); LC-MS: Calcd for C H O [M + H] ,
(CDCl , 100 MHz,): δ = 188.6 (C = O, C-1), 149.8 (Ar-C,
2
3
29 29
5
3
4
57.5, found: 457.2.
C-7, C-7′), 149.0 (Ar-C, C-6, C-6′), 143.0 (Ar-CH = CH-,
C-3, C-3′), 129.0 (Ar-C, C-4, C-4′), 124.0 (Ar-CH = CH-,
C-2, C-2′), 122.5 (Ar-C, C-9, C-9′), 113.7 (Ar-C, C-8, C-
8′), 110.5 (Ar-C, C-5, C-5′), 78.0 (-C ≡ CH-), 76.3 (-C ≡
CH-), 56.6 (Ar-OCH ), 56.0 (OCH ); LC-MS: Calcd for
(
2E,5E)-2,5-Bis(3-methoxy-4-(prop-2-yn-1-yloxy)
benzylidene)cyclopentanone (4e)
2
3
+
Yellow coloured crystal; yield 83%; mp: 178–180 °C; IR
C H O [M + H] , 403.4, found: 403.1
25 23 5
−
1 1
(
(
KBr) νmax 3251, 2117, 1671, 1580, 1503 cm ; H NMR
CDCl , 400 MHz,): δ = 7.78 (2H, s, Ar-CH = C-, H-3, H-
(2E,6E)-2,6-Bis(3,5-dichloro-2-(prop-2-yn-1-yloxy)
3
3
′), 7.10 (2H, d, J = 8.4 Hz, Ar-H, H-9, H-9′), 7.03 – 6.98
benzylidene)cyclohexanone (4h)
(
4H, m, Ar-H, H-5, H-5′, H-8, H-8′), 4.84 (4H, d, J =
2
2
1
7
1
1
.4 Hz, Ar-OCH ), 3.93 (6H, s, -OCH ), 2.57 (2H, d, J =
Yellow coloured crystal; yield 84%; mp: 146–148 °C; IR
(KBr) νmax 3243, 2109, 1661, 1560, 1423 cm ; H NMR
2
3
13
−1 1
.4 Hz, -C ≡ CH), 2.50 (4H, s, -CH2); C NMR (CDCl3,
00 MHz,): δ = 196.4 (C = O, C-1), 149.1 (Ar-C, C-7, C-
′), 148.5 (Ar-C, C-6, C-6′), 136.0 (Ar-CH = C-, C-3, C-3′),
33.9 (Ar-CH = C-, C-2, C-2′), 130.4 (Ar-C, C-4, C-4′),
24.3 (Ar-C, C-9, C-9′), 115.8 (Ar-C, C-8, C-8′), 114.6 (Ar-
(CDCl , 400 MHz,): δ = 7.87 (2H, s, Ar-CH = C-, H-3, H-
3
3′), 7.42 (2H, d, J = 2.4 Hz, Ar-H, H-7, H-7′), 7.22 (2H, d,
J = 2.4 Hz, Ar-H, H-5, H-5′), 4.71 (4H, d, J = 2.4 Hz, Ar-
OCH ), 2.78 (4H, t, J = 8.0 Hz, -CH -CH -CH ), 2.54 (2H,
2
2
2
2
C, C-5, C-5′), 78.5 (-C ≡ CH-), 76.4 (-C ≡ CH-), 64.8 (Ar-
t, J = 2.4 Hz, -C ≡ CH), 1.82-1.76 (2H, m, -CH -CH -CH );
2
2
2
1
3
OCH ), 56.8 (-OCH ), 26.5 (-CH ); ESI-MS: Calcd for
C NMR (CDCl , 100 MHz,): δ = 189.0 (C = O, C-1),
2
3
2
3
+
C H O [M + H] , 429.5, found: 430.0
151.3 (Ar-C, C-9, C-9′), 138.8 (Ar-CH = C-, C-3, C-3′),
33.3 (Ar-CH = C-, C-2, C-2′), 131.3 (Ar-C, C-7, C-7′),
2
7
25
5
1
(
1
1E,4E)-1,5-Bis(3-ethoxy-4-(prop-2-yn-1-yloxy)phenyl)penta-
,4-dien-3-one (4f)
130.2 (Ar-C, C-6, C-6′), 129.7 (Ar-C, C-5, C-5′), 129.5 (Ar-
C, C-8, C-8′), 128.5 (Ar-C, C-4, C-4′), 77.8 (-C ≡ CH-),
6
1.0 (Ar-OCH ), 28.5 (-CH ), 22.7 (-CH ); LC-MS: Calcd
2 2 2
+
Yellow coloured crystal; yield 85%; mp: 144–146 °C; IR
for C H Cl O [M] , 520.2, found: 520.0
26 18 4 3
−
1 1
(
(
KBr) νmax 3263, 2120, 1645, 1579, 1502 cm ; H NMR
CDCl , 400 MHz,): δ = 7.67 (2H, d, J = 16 Hz, Ar-CH =
(1E,4E)-1,5-Bis(3,5-dichloro-2-(prop-2-yn-1-yloxy)phenyl)
3
C-, H-3, H-3′), 7.20 (2H, dd, J = 8.4 Hz and 2 Hz, Ar-H, H-
, H-9′), 7.16 (2H, d, J = 2 Hz, Ar-H, H-5, H-5′), 7.06 (2H,
penta-1,4-dien-3-one (4i)
9
d, J = 8.4 Hz, Ar-H, H-8, H-8′), 6.95 (2H, d, J = 16 Hz, Ar-
CH = CH-, H-2, H-2′), 4.82 (4H, d, J = 2.4 Hz, Ar-OCH2),
Yellow coloured crystal; yield 80%; mp: 181–183 °C; IR
(KBr) νmax 3285, 2126, 1664, 1599, 1554 cm ; H NMR
−
1 1
4
2
.15 (4H, q, J = 7.2 Hz, -OCH CH ), 2.54 (2H, d, J =
(CDCl , 400 MHz,): δ = 8.03 (2H, d, J = 16 Hz, Ar-CH =
2
3
3
1
3
.4 Hz, -C ≡ CH), 1.50 (6H, t, J = 7.2 Hz, -OCH -CH );
C
C-, H-3, H-3′), 7.57 (2H, d, J = 2.4 Hz, Ar-H, H-7, H-7′),
7.45 (2H, d, J = 2.4 Hz, Ar-H, H-5, H-5′), 7.12 (2H, d, J =
16 Hz, Ar-CH = CH-, H-2, H-2′), 4.78 (4H, d, J = 2.4 Hz,
2
3
NMR (CDCl , 100 MHz,): δ = 188.8 (C = O, C-1), 149.3
3
(
Ar-C, C-7, C-7′), 149.2 (Ar-C, C-6, C-6′), 143.0 (Ar-CH
1
3
=
CH-, C-3, C-3′), 129.0 (Ar-C, C-4, C-4′), 124.0 (Ar-CH
Ar-OCH ), 2.57 (2H, t, J = 2.4 Hz, -C ≡ CH); C NMR
2