4
Journal of Chemistry
(E)-3-(3-Methoxyl-4-hydroxy phenyl) Propyl Acrylate (6c).
(E)-2-Acetoxyl Benzoic Acid-[4-(3-oxethyl-3-oxo-1-propenyl)-
1
Yellow oil, 77% yield. 1H NMR (CDCl , 300 MHz) ꢄ: 1.01 (t,
2-methoxyl] Phenyl Ester (7b). Yellow solid, 48% yield. H
3
ꢃ = 6.8 Hz, 3H, CH ), 1.75 (m, 2H,CH ), 3.94 (s, 3H, OCH ),
NMR (CDCl , 300 MHz) ꢄ: 1.37 (t, ꢃ = 7.1 Hz, 3H, CH ),
3
2
3
3
3
4.15 (t, ꢃ = 7.4 Hz, 2H, COOCH ), 6.31 (d, ꢃ = 15.9 Hz, 1H,
2.32 (s, 3H, COCH ), 3.88 (s, 3H, OCH ), 4.28 (q, ꢃ = 7.1 Hz,
2
3
3
C=CH), 6.93 (d, ꢃ = 8.0 Hz, 1H, Ar-H), 7.05 (m, 2H, Ar-H),
7.63 (d, ꢃ = 15.9 Hz, 1H, CH=C); ESI-MS: m/z 237 [M+H]+.
2H, COOCH ), 6.42 (d, ꢃ = 15.9 Hz, 1H, C=CH), 7.18 (m,
2
4H, Ar-H), 7.39 (m, 1H, Ar-H), 7.68 (m, 2H, Ar-H), 8.26 (d,
ꢃ = 15.9 Hz, 1H, CH=C); ESI-MS: m/z 385 [M+H]+.
(E)-3-(3-Methoxyl-4-hydroxy phenyl) Isopropyl Acrylate (6d).
Red solid, 69% yield. 1H NMR (CDCl , 300 MHz) ꢄ: 1.32 (d,
(E)-2-Acetoxyl Benzoic Acid-[4-(3-propoxy-3-oxo-1-propenyl)-
2-methoxyl] Phenyl Ester (7c). Yellow solid, 43% yield. H
3
1
ꢃ = 6.2 Hz, 6H, 2CH ), 3.92 (s, 3H, OCH ), 5.14 (m, 1H,
3
3
COOCH), 6.27 (d, ꢃ = 15.9 Hz, 1H, C=CH), 6.91 (d, ꢃ =
8.0 Hz, 1H, Ar-H), 7.03 (m, 2H, Ar-H), 7.60 (d, ꢃ = 15.9 Hz,
1H, CH=C); ESI-MS: m/z 237 [M+H]+.
NMR (CDCl , 300 MHz) ꢄ: 1.00 (t, ꢃ = 7.4 Hz, 3H, CH ),
3
3
1.74 (m, 2H, CH ), 2.30 (s, 3H, COCH ), 3.86 (s, 3H, OCH ),
2
3
3
4.18 (t, ꢃ = 6.8 Hz, 2H, COOCH ), 6.42 (d, ꢃ = 15.9 Hz, 1H,
2
C=CH), 7.8 (m, 4H, Ar-H), 7.39 (m, 1H, Ar-H), 7.68 (m, 2H,
Ar-H), 8.26 (d, ꢃ = 15.9 Hz, 1H, CH=C); ESI-MS: m/z 399
[M+H]+.
(E)-3-(3-Methoxyl-4-hydroxy phenyl) Butyl Acrylate (6e). Red
1
oil, 73% yield. H NMR (CDCl , 300 MHz) ꢄ: 0.97 (t, ꢃ =
3
7.3 Hz, 3H, CH ), 1.45 (m, 2H, CH ), 1.69 (m, 2H, CH ), 3.93
3
2
2
(s, 3H, OCH ), 4.20 (t, ꢃ = 6.6 Hz, 2H, COOCH ), 6.29 (d,
(E)-2-Acetoxyl Benzoic Acid-[4-(3-isopropoxy-3-oxo-1-propenyl)-
2-methoxyl] Phenyl Ester (7d). Yellow oil, 46% yield. 1H NMR
(CDCl , 300 MHz) ꢄ: 1.32 (d, ꢃ = 6.2 Hz, 6H, 2CH ), 2.30 (s,
3
2
ꢃ = 15.9 Hz, 1H, C=CH), 6.92 (d, ꢃ = 8.0 Hz, 1H, Ar-H), 7.04
(m, 2H, Ar-H), 7.61 (d, ꢃ = 15.9 Hz, 1H, CH=C); ESI-MS: m/z
251 [M+H]+.
3
3
3H, COCH ), 3.84 (s, 3H, OCH ), 5.15 (m, 1H, COOCH), 6.39
3
3
(d, ꢃ = 15.9 Hz, 1H, C=CH), 7.14 (m, 4H, Ar-H), 7.36 (m, 1H,
Ar-H), 7.66 (m, 2H, Ar-H), 8.24 (d, ꢃ = 15.9 Hz, 1H, CH=C);
ESI-MS: m/z 399 [M+H]+.
(E)-3-(3-Methoxyl-4-hydroxy phenyl) Isobutyl Acrylate (6f ).
Yellow oil, 63% yield. 1H NMR (CDCl , 300 MHz) ꢄ: 0.98 (d,
3
ꢃ = 6.8 Hz, 6H, 2CH ), 2.03 (m, 1H, CH), 3.92 (s, 3H, OCH ),
3
3
3.98 (d, ꢃ = 6.6 Hz, 2H, COOCH ), 6.30 (d, ꢃ = 15.9 Hz, 1H,
(E)-2-Acetoxyl Benzoic Acid-[4-(3-butoxy-3-oxo-1-propenyl)-
2
1
C=CH), 6.91 (d, ꢃ = 8.0 Hz, 1H, Ar-H), 7.05 (m, 2H, Ar-H),
7.62 (d, ꢃ = 15.9 Hz, 1H, CH=C); ESI-MS: m/z 251 [M+H]+.
2-methoxyl] Phenyl Ester (7e). Yellow solid, 41% yield. H
NMR (CDCl , 300 MHz) ꢄ: 0.97 (t, ꢃ = 7.4 Hz, 3H, CH ),
3
3
1.42 (m, 2H, CH ), 1.69 (m, 2H, CH ), 2.28 (s, 3H, COCH ),
2
2
3
(E)-3-(3-Methoxyl-4-hydroxy phenyl) Amyl Acrylate (6g). Yel-
3.82 (s, 3H, OCH ), 4.21 (t, ꢃ = 6.6 Hz, 2H, COOCH ), 6.40
1
3
2
low oil, 58% yield. H NMR (CDCl , 300 MHz) ꢄ: 0.88 (m,
3
(d, ꢃ = 15.9 Hz, 1H, C=CH), 7.16 (m, 4H, Ar-H), 7.37 (m, 1H,
Ar-H), 7.64 (m, 2H, Ar-H), 8.22 (d, ꢃ = 15.9 Hz, 1H, CH=C);
ESI-MS: m/z 413 [M+H]+.
3H, CH ), 1.36 (m, 4H, 2CH ), 1.70 (m, 2H, CH ), 3.91 (s,
3
2
2
3H, OCH ), 4.20 (t, ꢃ = 6.7 Hz, 2H, COOCH ), 6.28 (d,
3
2
ꢃ = 15.9 Hz, 1H, C=CH), 6.90 (d, ꢃ = 8.0 Hz, 1H, Ar-H), 7.04
(m, 2H, Ar-H), 7.60 (d, ꢃ = 15.9 Hz, 1H, CH=C); ESI-MS: m/z
265 [M+H]+.
(E)-2-Acetoxyl Benzoic Acid-[4-(3-isobutoxy-3-oxo-1-propenyl)-
1
2-methoxyl] Phenyl Ester (7f ). Yellow solid, 45% yield. H
NMR (CDCl , 300 MHz) ꢄ: 0.99 (d, ꢃ = 6.8 Hz, 6H, 2CH ),
3
3
(E)-3-(3-Methoxyl-4-hydroxy phenyl) Isoamyl Acrylate (6h).
2.01 (m, 1H, CH), 2.30 (s, 3H, COCH ), 3.84 (s, 3H, OCH ),
Yellow oil, 46% yield. 1H NMR (CDCl , 300 MHz) ꢄ: 0.95 (d,
3
3
3
4.00 (d, ꢃ = 6.6 Hz, 2H, COOCH ), 6.42 (d, ꢃ = 15.9 Hz, 1H,
2
ꢃ = 6.6 Hz, 6H, 2CH ), 1.56 (m, 2H, CH ), 1.81 (m, 1H, CH),
3
2
C=CH), 7.16 (m, 4H, Ar-H), 7.37 (m, 1H, Ar-H), 7.66 (m, 2H,
Ar-H), 8.24 (d, ꢃ = 15.9 Hz, 1H, CH=C); ESI-MS: m/z 413
[M+H]+.
3.91 (s, 3H, OCH ), 4.22 (t, 2H, ꢃ = 6.8 Hz, COOCH ), 6.29
3
2
(d, ꢃ = 15.9 Hz, 1H, C=CH), 6.91 (d, ꢃ = 8.0 Hz, 1H, Ar-H),
7.07 (m, 2H, Ar-H), 7.61 (d, ꢃ = 15.9 Hz, 1H, CH=C); ESI-MS:
m/z 265 [M+H]+.
(E)-2-Acetoxyl Benzoic Acid-[4-(3-pentyloxy-3-oxo-1-propenyl)-
1
2-methoxyl] Phenyl Ester (2g). Yellow solid, 42% yield. H
3.2. General Procedure for the Preparation of 7a–7h. To a stir-
ring solution of 6 (1.0 mmoL), DCC (618 mg, 3 mmoL), and
DMAP (73.2 mg, 0.60 mmoL) in dichloromethane (50 mL)
aspirin (540 mg, 3 mmoL) was added at room temperature.
en the mixture was stirred at 25∘C for 3-4 h. Afer being fil-
tered and concentrated, the target compounds were obtained
by column chromatography (ethyl acetate-petroleum ether).
NMR (CDCl , 300 MHz) ꢄ: 0.95 (t, ꢃ = 6.8 Hz, 3H, CH ),
3
3
1.39 (m, 2H, CH ), 1.55 (m, 2H, CH ), 1.72 (m, 2H, CH ),
2
2
2
2.30 (s, 3H, COCH ), 3.86 (s, 3H, OCH ), 4.21 (t, ꢃ = 6.8 Hz,
3
3
2H, COOCH ), 6.41 (d, ꢃ = 15.9 Hz, 1H, C=CH), 7.16 (m,
2
4H, Ar-H), 7.39 (m, 1H, Ar-H), 7.66 (m, 2H, Ar-H), 8.25 (d,
ꢃ = 15.9 Hz, 1H, CH=C); MS ESI-MS: m/z 427 [M+H]+.
(E)-2-Acetoxyl Benzoic Acid-[4-(3-isopentylvoxy-3-oxo-1-pro-
penyl)-2-methoxyl] Phenyl Ester (7h). Yellow solid, 42% yield.
1H NMR (CDCl , 300 MHz) ꢄ: 0.97 (brs, 6H, 2CH ), 1.60 (m,
(E)-2-Acetoxyl Benzoic Acid-[4-(3-methoxyl-3-oxo-1-propenyl)-
1
2-methoxyl] Phenyl Ester (7a). Yellow solid, 42% yield. H
3
3
2H, CH ), 1.81 (m, 1H, CH), 2.30 (s, 3H, COCH ), 3.84 (s,
NMR (CDCl , 300 MHz) ꢄ: 2.33 (s, 3H, COCH ), 3.86 (s, 3H,
2
3
3
3
3H, OCH ), 4.25 (d, ꢃ = 6.8 Hz, 2H, COOCH ), 6.41 (d, ꢃ =
OCH ), 3.89 (s, 3H, COOCH ), 6.44 (d, ꢃ = 15.9 Hz, 1H,
3
2
3
3
15.9 Hz, 1H, C=CH), 7.12 (m, 4H, Ar-H), 7.37 (m, 1H, Ar-H),
7.64 (m, 2H, Ar-H), 8.25 (d, ꢃ = 15.9 Hz, 1H, CH=C); ESI-MS:
m/z 427 [M+H]+.
C=CH), 7.20 (m, 4H, Ar-H), 7.44 (m, 1H, Ar-H), 7.70 (m, 2H,
Ar-H), 8.28 (d, ꢃ = 15.9 Hz, 1H, CH=C); ESI-MS: m/z 371
[M+H]+.